Basic Tables For Chemical Analysis

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.^'^^r"^
AlllDb 3MD1D7
<5
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^''ffCAU O* " NBS TECHNICAL NOTE 1096
U.S. DEPARTMENT OF COMMERCE / National Bureau of Standards
Basic Tables for Chemical

Analysis
Thomas J. Bruno
Paris D.N.Svoronos
QC
100
.U5753
#1096
1
_ _ >"
1986
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i\!< RESEARCH
3EAR(
INFORMATION
.ô CENTER
Basic Tables for Chemical Analysis ^^^
Thomas J. Bruno
Thermophysics Division
Center for Chemical Engineering
National Engineering Laboratory
National Bureau of Standards
Boulder, Colorado 80303
Paris D.N. Svoronos

Department of Chemistry
Queensborough Community College
City University ofNew York
Bayside, New York 11364
and
Georgetown University
Washington, DC 20057
U.S. DEPARTMENT OF COMMERCE, Malcolm Baldrlge, Secretary
NATIONAL BUREAU OF STANDARDS, Ernest Ambler, Director
Issued April 1986

National Bureau of Standards Technical Note 1096
Natl. Bur. Stand. (U.S.), Tech Note 1096, 240 pages (Apr. 1986)
CODEN:NBTNAE
U.S. GOVERNMENT PRINTING OFFICE

WASHINGTON; 1986
For sale by the Superintendent of Documents, U.S. Government Printing Office, Washington. DC 20402
CONTENTS
Page
Abstract 1
Introduction 1
I. Tables for Gas Chromatography 5
Mesh Sizes and Particle Diameters 7
Gas Chromatographic Support Materials 9
Carrier Gas Properties 12
Properties of Some Liquid Phases 15
Stationary Phases for Packed Column Gas Chromatography 33
Silicone Liquid Phases 35
Adsorbents for Gas-Solid Chromatography 48
Porous Polymer Phases 51
Cryogens for Subambient Temperature Gas Chromatography 58
Some Useful Fluids for Supercritical Fluid Chromatography 60
II. Tables For Liquid Chromatography 61
Solvents for Liquid Chromatography 63
Modes of Liquid Chromatography 66
Reverse Phase Materials and Solvents 67
HPLC Column Packings 68
III. Tables for Ultraviolet Spectrophotometry 71
Solvents for Ultraviolet Spectrophotometry 73

Transmittance - Absorbance Conversion 76
Correlation Table for Ultraviolet Active Functionalities 80
IV. Tables for Infrared Spectrophotometry 85
Infrared Optics Materials 87
Wavelength - Wavenumber Conversion Table 91
Useful Solvents for Infrared Spectrophotometry 94
acetonitrile 95
benzene 96
bromof orm 97
111
CONTENTS (cont.)
Page
carbon disulfide 98
carbon tetrachloride 99
chloroform 1 00
cyclohexane 1 01
dimethyl sulfoxide 1 02
1 ,
4- dioxane 1 03
ethyl acetate 1 04
n-hexane 105
isopropanol 1 06
methyl ethyl ketone 107
n-octane 108
paraffin oil 1 09
tetrahydrof uran 110
toluene Ill
Polystyrene Wavenumber Calibration 112
IR Correlation Chart 113

Aromatic Substitution Bands 114
Infrared Absorptions of Major Chemical Far:ilies 115
Hydrocarbon Compounds 116
Organic Oxygen Compounds 122
Organic Nitrogen Compounds 137

Organic Sulfur Compounds 146
Organic Silicon Compounds 149
Organic Phosphorous Compounds 150
Organic Halogen Compounds 152
V. Tables for Nuclear Magnetic Resonance Spectroscopy 155
Tables for Nuclear Magnetic Resonance Spectroscopy 157
Magnetic Properties of Some Nuclei 158
NMR Correlation Chart 1 59
Proton NMR Absorptions of Major Chemical Families 1 60
Hydrocarbons 1 61
Organic Oxygen Compounds 162
Organic Nitrogen Compounds 166
IV
CONTENTS (cont.)
Page
Organic Sulfur Compounds 169
Some Useful ^H Coupling Constants 171
Solvent Positions of Residual (Impurity) Protons

in Incompletely Deuterated Solvents 172
^^C Chemical Shifts of Useful NMR Solvents 174
VI. Tables for Mass Spectrometry 1 77
Natural Abundance of Important Isotopes 179
Rules for Determination of Molelcular Formula I8l
Chlorine - Bromine Combination Isotope Intensities 183

Common Fragmentation Pattern of Families of Organic Compounds. .. 1 86
VII. Tables for Qualitative Analysis 193
Organic Group Qualitative Tests 195
Protocol for Chemical Tests 197
Inorganic Group Qualitative Tests 207

Acid (Anion) Tests 208
Metal (Cation) Tests 211
VIII. Miscellaneous Tables 21 7
Common Drying Agents for Organic Liquids 219

Flammability Hazards of Common Solvents 221
Properties of Hazardous Solids 225

Hazardous Material Log Sheet 229
Unit Conversions 230
BASIC TABLES FOR CHEMICAL ANALYSIS
THOMAS J. BRUNO
Thermophysics Division
Center for Chemical Engineering
Boulder, CO 80303
and
PARIS D.N. SVORONOS

Queensborough Community College
City University of New York
Bayside, NY 11364
and
Georgetown University
Washington, DC 20057
Tables of important data for use in the analytical

chemistry laboratory are provided. These tables contain
information for use in gas chromatography, liquid
chromatography, infrared and ultraviolet spectrophotometry,
mass spectrometry, and wet chemical techniques. Tables
relating to safe practice in the analytical laboratory
are also included.
Key words: chemical analysis; instrumental analysis.
Introduction
This set of tables is intended to serve as a handy reference for both the
practicing chemist and student. Included are data which are not easily
obtainable elsewhere, collected in a source which is intended to reduce the
need for consulting a bookshelf of reference works in the daily practice of
analytical chemistry.
This technical note grew out of a booklet of tables which accompanied a
series of lectures on analytical chemistry presented by one of the authors
(T.J.B) for the professional staff and students working at the National Bureau
of Standards Boulder Laboratories. That booklet has now been expanded and
augmented by the authors in this volume. The primary purpose of these tables
is to support the teaching and research activities of the authors, and it is
offered to the scientific community as a low-cost source of useful information
for the practicing scientist.
The topics covered in this volume include gas chromatography, liquid
chromatography, thin layer chromatography, infrared and ultraviolet
spectrophotometry, mass spectrometry , and "wet" chemical tests. Aspects of
safety in the analytical laboratory are also considered. Topics such as
atomic absorption, x-ray methods, and electroanalytical chemistry have not
been included in the present volume but will be included in a future edition.
While the authors have endeavored to include data and information which
they perceive to be most useful, there will undoubetdly be areas which have
been slighted. V/e therefore ask you, the reader, to assist us in this regard
and inform the corresponding author (T.J.B.) of any topics which should be
included in future editions. The authors have made every effort to provide
correct and up-to-date information in this volume. For the occasional mistake
which may have crept into these pages, however, each author blames the other.
The authors would like to acknov/ledge the assistance of Juli Schroeder in
the preparation of several of these tables. Terry Yenser, Barb Powers, and
Marlene Deutsch are to be thanked for the excellent word processing services.
The authors would like to acknowledge one of their teachers. Professor Charles
F. Hammer of Georgetwon University, who taught them much of what they know
about spectroscopy. One of the authors (T.J.B.) gratefully acknowledges the
financial support of the Gas Research Institute and the United States
Department of Energy, Office of Basic Energy Sciences.
DISCLAIMER
CERTAIN COMMERCIAL EQUIPMENT, INSTRUMENTS, OR MATERIALS ARE IDENTIFIED IN
THIS TECHNICAL NOTE IN ORDER TO PROVIDE AN ADEQUATE DESCRIPTION. SUCH
IDENTIFICATION DOES NOT IMPLY RECOMMENDATION OR ENDORSEMENT BY THE NATIONAL
BUREAU OF STANDARDS, NOR DOES IT IMPLY THAT THE MATERIALS OR EQUIPMENT
IDENTIFIED ARE NECESSARILY THE BEST AVAILABLE FOR THE PURPOSE.
Note
Occasional use is made of non-SI units in order to conform to standard and
accepted practice in modern analytical chemistry.

I. Tables for Gas
Chromatography
—
Mesh Sizes and Particle Diameters
The following tables give the relationship between particle size diameter
(in ym) and several standard sieve sizes. The standards are as follows:
United States Standard Sieve Series, ASTM E-11-61
Canadian Standard Sieve Series, 8-GP-16
British Standards Institution, London, BS-il10-62
Japanese Standard Specification, JI S-Z-8801
French Standard, AFNOR X-1 1-501
German Standard, DIN-41 88
Particle British Japanese Canadian

Size, U.S. Sieve Tyler Mesh Sieve Sieve Sieve
ym Size Size Size Size Size
4000 5 — ——
2000
—9.2
10 9 8 8
1680 12 10 — —
1420 14 12 — — —
1190 16 14 — — —
1000 18 16 — — —
841 20 20 18 20 18
707 25 24 — — —
595 30 28 25 28 25
500 35 32 — — —
420 40 35 36 36 36
354 45 42 — — —
297 50 48 52 52 52
250 60 60 60 55 60
210 70 65 72 65 72
177 80 80 85 80 85
149 100 100 100 100 100
125 120 115 120 120 120
105 140 150 150 145 150
88 170 170 170 170 170
74 200 200 200 200 200
63 230 250 240 250 240
53 270 — 300 280 300
44 325 — 350 325 350
37 400 — — —
French and German
Sieve Sizes
Particle Sieve
size, ym size
2000 34
800 30
500 28
400 27
315 26
250 25
200 zn
160 23
125 22
100 21
80 20
63 19
50 18
40 17
Gas Chromatographic Support Materials
The following table lists the more common solid supports used in packed
column gas chromatography, along with relevant properties [1-M]. The
performance of several of these materials can be improved significantly by
acid washing and treatment with DMCS (dimethyldichlorosilane) to further
deactivate the surface. Most of the materials are available in several
particle size ranges. The use of standard sieves will help insure
reproducible packings from one column to the next.
REFERENCES
[1 ] Poole, C.F., Schuette, S.A., Contemporary Practice of Chromatography ,
Elsevier, Amsterdam, 1984.
[2] Gordon, A. J., Ford, R.A., The Chemist's Companion , John Wiley and Sons,
New York, 1972.
[3] Heftmann, E., ed., Chromatography; A Laboratory Handbook of Chromato-

graphic and Electrophoretic Methods 3i"d ed.. Van Nostrand Reinhold, New
,
York, 1975.
[4] Grant, D.W., Gas Liquid Chromatography , Van Nostrand Reinhold, London,
1971 .
gas
low
high than
low sur- surface °C; com-
to deform
density.
for
strength; separations
250
compounds.
compound
due
preparative
to
capacity;
low
moderate
strength
of polarity
useful
strength; high strength;
high
tends
polar polar
for very difficult
phase
high
for temperature
activity. activity; for

mechanical
capacity;
mechanical mechanical
is charge;
compressed;
of
supports;
activity;
useful liquid
moderately
.
chromatography;
separation.
CO
analysis
CD surface surface activity; maximum handling pounds
liquid static
-P lower pink
o most high high high face when
2 of
i.
O JJ 4J -p
r-i c CO —1 c — f-<
o i-i >> x: x:
o CX o 3 CX 3 3
6^ 6^
Maximum
liquid loading
C\J
in o
CV-1
LTi
Surface
in O O in
area
mVg o
LP. LH
=
I^ CO CO
g/mL
CO 0^
(packed LO C\J
Density
o o o o o
fall)
g/mL
CO CO CM
Density
(free
o o o o o
c
CD
t,
>,
^ (D
p)
x:
J-)
•.-1 •r-l -.H •^ CD
E E S- E O
Support
type
O diatomite O Xi O t.
pi P) jJ o
CO CO t. CO D
•r-l r-l i-H
•o a CO
jJ
CD
P)
A G T >,
I—
-p X5 O
CX
o <x> o O
ClE CO CO
CXCO o o
D C Chromosorb Chromosorb
E E Chromosorb
cyD O o
s_ L
x: x: a.
CJ) o
10
I
gas
low
high than
low sur- surface °C; com-
to deform
density.
for
strength; separations
250
compounds.
compound
due
preparative
to
capacity;
low
moderate
strength
of polarity
useful
strength; high strength;
high
tends
polar polar
for very difficult
phase
high
for temperature
activity. activity; for

mechanical
capacity;
mechanical mechanical is charge;

compressed;
of
supports;
activity;
useful
liquid
moderately
chromatography;
separation.
CO
analysis
surface surface activity; maximum handling pounds.
liquid
p> lower pink
static
o most high high high face
of
when
2:
O p> p>
<-\ c CO rH c rH rH
o r-i >> x; x; x:
o CX O 3 CX 3 3
&S.
Maximum
liquid loading
LO
C\J
in o
m in LPl
Surface
in o o LTl
area
mVg
C\J o -3- C—
in LTi LO
Q. 1^ CX) OO
g/mL
CO c» CTn
(packed) LO CNJ
Density
o o O o O
fall)
g/mL
o CX) CO CM
Density
(free
o o o o O
c
>,
^ x:
pi pio •p -p
rH M rH iH
E E E L E o
Support
type
O O O XI o
4^ pi pi o
03 03 03 t, 03 3
rH '>-{ •t-\ r-l rH
a a CD Cm a. Cm
03
JP
-P
o :3 >,
I—
XI X) X) X) XI O
L J- CX
O O O O o o
a.E CO CO CO CO CO
D.03 O O o o
3 C E i E E E
00 O O o o
u H
x; x: X k x; a.
o o o o
11
Carrier Gas Properties
The following table gives the properties of common gas chromatographic
carrier gases. These properties are those used most often in designing
separation and optimizing detector performance. The density values are
determined at 0°C and 0.101 MPa (760 Torr) [1]. The thermal conductivity
values are determined at 48.9°C (120°F) [1]. The viscosity values are
determined at the temperatures listed, and at 0.101 MPa (760 Torr) [1]. The
heat capacity (constant pressure) values are determined at 15°C and 0.101 MPa
(760 Torr) [2].
REFERENCES
[1 ] Weast, R. C, ed., Handbook of Chemistry and Physics , 63rd ed., CRC

Press, Boca Raton, 1983.
[2] Dal Nogare, S., Juvet, R. S. Gas-Liquid Chromatography: Theory and

,
Practice, John Wiley and Sons Interscience ) New York, 1962.

( ,
12
CY-l
o o
O o o o O o
Molecular
Weight
CM CM OO OO
OO CM CM
1^ U3 OO
O O o
OO OO
Heat
Capacity
(J/kg-K)
OO CM CJ^ O o
CM
(20.7°C) 4°C) 0°C) (20.0°C) 0°C) 0°C) O

o
O
o
O
o
O
o
CJ
o o
O O O O
o o o
o o o
o o o
O O LPi <— t^ O ^ CM I>- l>- o
t^-
O O O
CM O O
CT^
^ t>-
CM C^
1^ l>-
CM
t- ^
CM
^ vr>
CM CM CM
[^-
Viscosity
(Pa's)
(129. (299. (100. (200.
^^ ^ CM --^ ^ CM ^ CM
.- CM v-' — 0^
t- ^ LO CO OO i>- ^ ^ C3^ OO ro CO
CO OO o r- >X) t— OO CT^ LTi LT^ CO
^
^
0.876 1.086 1.381 1.941 2.281 2.672 O OO ^D o...
in o C- >- LP, t>- LO
CM CM CV-) ^ CM CM ^ CM CM
LTi
(Ar)
oo CO CO CJ> CO
.
6X
OO o O o
ivity
(NJ C7^ o OO
Conduct
.
en o
o o
1
Difference
CM 1 o
SX 1
al
Therm o C7^
(He)
1 O CO CJ^ o
1
CO CM Cv) CM OO
6A
1 7 1 1
10-2
LO LOi
1^ OO ô
Thermal Conductivity (W/m-K) 1
LTi oo cm' CM* CVJ

X
OO o LPi o
CO OO o LPi
CTn
CO
CO O
LTi
o
LTi
Density (kg/m^)
O ^3" CM
o O o
C
CD CD
Carrier Gas faO C c
o ::! CO CD
monoxide
x: faO nitrogen
carbon
r-H >>
>> CD CD X
E o
13
in ^3- CM O
o o O O
Molecular
Weight
o
on
CO
C\J ^5- on
CO
LO
o o
>-o
Heat
1 1 CM 1
Capacity
(J/kg.K)
1 1 LPl CO 1
O
o
CJ>
o
o
o
o o
o o o
(l; o o o
o o o
O
o o o
CJ
CLJ o
o
o o
o o o
O
o
>> C\J -^ CYI O O O <J^ .=r CY^ O O O O r- =r
.^
CO
in ^-^
CO
t-O O
^ O O
COO
O O
CM
tr—
.—
O
O
0>
CTv
O O O
CM O O
O
CM
CM
CTi
CO
cr> CM
^
1
O
O
O
^ •
03
v-^ r- C\J -^ CM -—- .^ CM
X
•M
CO
—
a.
^ m cr cc ^- ^ LO CJ^ ro f- ir^ oo O ^ ^ O O
> O >— o
C3>
-^S"
.:T
O
O
LH
CM
^
LTi
C3^
I>-
O
O
LPi
(\J
^ C7^ CM
CM <D CM
CO Ô CM
^ CO CM
in
.=3-
CD ^ ^ o' ^ ^ CM CM CO ^ ^ cm' O
on C~- cx)
(Ar)
In
^ 1 O o CM
1
6X
o ° (3 O1
o
1
O
1
ivity
Conduct (N^)
CM LTi
CO
CM
CJN
m CM
Difference
o O O O O o
6\ 1 1 1 1 1 1 1
al
Therm
(He)
o 0^
CM
r>~i CO CTn
6X
no
,_
m on .3-
1 1 1 1 1 1
o o CM CO
Conductivity
10"'
(W/m-K) .
en o C7^ CO CO
Thermal
C\J CM cm'
X
o o O o O c O
vO o o
in
o CT>
O
m
CO
C7^
O
O
CM
Density (kg/m^)
m C\J O CJ^ LO •—
CM CM
CD
X3
•rH
r-l CO 0) 0) C
t, CO CD c c -o 03
t. o c c 03 c O -rH D Ci-i
CO 03 Q) Ci. o £1 X <;-< 03
o x:
4->
SZ
4-3
O bO t, o
•-<
i-H
3
X
J- 03 1
03 o -a C CO -C
14
Properties of Some Liquid Phases
The following table lists some of the more common gas-chromatographic
liquid phases, along with some relevant data and notes [1,2], Most of these
have been largely superseded by silicone phases used in capillary columns, but
these liquid phases still find application in many instances. The minimum
temperatures, where reported, indicate the point at which some of the phases
approach solidification, or when the viscosity increases to the extent that
performance is adversely effected. The maximum working temperatures are
determined by vapor pressure (liquid phase bleeding) and chemical stability
considerations. The liquid phases are listed by their most commonly used
names. Where appropriate, chemical names or common generic names are provided
in the notes.
The McReynolds constants tabulated here are based on the retention
characteristics of the following test probe samples:
Constant Test probe
X benzene
Y 1-butanol
Z 3~pentanone
U 1 -nitroporpane
S pyridine
Compounds which are chemically similar to these probe solutes will show
similar retention characteristics. Thus, benzene can be thought of as
representing lower aromatic or olefinic compounds. Higher values of the
McReynolds constant usually will indicate a longer retention time (higher
retention volume) for a compound represented by that constant, for a given
liquid (stationary) phase.
15
Properties of Some Liquid Phases (cont.)
Solvents : Ace - acetone MeCl - methylene chloride
Chlor - chloroform Tol - toluene
Pent - pentane MeOH - methanol
DMP - dimethylpentane HjO - water
Polarity: N - nonpolar
P - polar
I - intermediate polarity
H. B. - hydrogen bonding
S - specific interaction
REFERENCES :
[1] McReynolds, W.O., J. Chroraatogr. Sci, 8, 685, 1970.
[2] McNair, H. ., Bonelli, E.J., Basic Gas Chromatography , Varian Aerograph,

Palo Alto, 1968.
16
1
)-2-
weakly -ethanol
CO C
CD 03 pressure pressure pressure pressure pressure pressure pressure
4-> oil oil oil oil oil oil oil

o 3
JD
(8-Heptadecenyl
C
03 oxazoline,
>,
vapor vapor vapor vapor vapor vapor vapor
•H hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon hydrocarbon
a
imidazoline-1
cationic
50^ 2- low
low low low low low low
CM CO
00
CM
m CM LO LH LP
CO -=r ro CM CM LP
c ^ C7^ LO CC) 00 LO LP
o CM
o
CO CM LO LPl CO cn
•a
M IS!
CM
5 CO CM CM C^
O -
c
CX3 CM CM LPl
>H C» in cn CM CM CY-)
CM
o
5:
t^ CO CM CO CM
00 LH en on ro 00 CO
X
CO
4->
c i.
rH rH a: rH rH rH r-\ rH
CD rH rH rH rH rH rH
rH x: x: x: x: x: x: X: x: jr. x:
00
E 2: s S s S S
>>
-P
•H
S-
03
-H
1—1 1— HH M Cu 2: ;s 2 s 2; 2 2;
+
X LO LO LP
OS CM 00 LO CX)
e CM 00 CY-) CM fv-1 CY-) CM
c LTi LO C3>
•H
E
1 CM in LO s cn S LPl LPl LP
'0
c c c
03
Jj) -H -P - -P
TD 3 E-<
X2 rH 1 03
03 C •H •H Cn
03 J_ L bO t, CM 2
rH X -P C- 3 CM
>. H CO c C c c c c
T3 c x: M>> -P C -P
N N
•rH 1 03 c N N [Si
3 C
-P Ln
HCX •H
CO 03
03 - -P ::< -H rH •r( •H •H •H •H •r-i
•rH x: CM -H 73 rH E CX CX CX Q. CX a.
J 03 -— 03 03 < 03 < < < < <
17
E
3
•rH
CD
acid
c
C aliphatic,
o
•rH
s
amine CO CO
hydrocarbon
f-H
o heterocyclic
fatty
>, CD
heptatetra-
•rH
of
O ,-t
-P CD CD •rH
CO CO rH
•rH
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X X X X X
26
(ethylene
acid (ethylene-
of a
100
CO
and phenoxypolyethyleneoxy
=
9
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CD aliphatic
30 n
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2 =
boiling pentaerythritol
n
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o o o o o
1
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1 1
Cu <- --' x: X. c x: x: hH HH HH HH HH HH CQ .rH
27
petroleum
c
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of
CO
CO (U
S-
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28
11 1 )
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29
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31
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glycol, glycol, glycol, glycol,
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32
stationary Phases for Packed Column Gas Chromatography
The following stationary phases have been shown to be useful in
separating the following classes of compounds, using coated packed columns.
The resolution obtained will probably be lower than that obtainable with
capillary columns. Alternative stationary phases are to be found in the
previous table.
Compounds Suggested Stationary Phase
- Alcohols
Ci - c. Hallcomid M-18 OL, Carbowax 600 - Carbowax 1540
*
r - c FFAP, Carbowax 20M
Di-Poly FFAP, QF-1, Porapak Q, Porapak QS
- Aldehydes
Ci - c. Ethofat
C 5 ~ Ci 8 Carbowax 20M
- Alkaloids QF-1, SE-30
- Amides Versamid 900, FFAP, Ethofat or Carbowax 600 (on

Chromosorb T)
- Amino Acid Derivatives DEGS/EGSS-X
- Amines Dowfax 9N9/KOH, Pennwalt 213, Chromosorb 103
- Boranes Apiezon L, Hexadecane, Octadecane, Squalane
- Essential Oils * ** FFAP, Carbowax 20M
- Esters DNP, Porapak Q
- Ethers Carbowax 1500 - 20M
- Glycols Porapak-Q, QF-1
- Halogen Compounds Carbowax 1500-20M, QF-1, FS-1265, FFAP Porapak

(for freons)
* - consider a capillary column
** - consider HPLC
33
stationary Phases for Packed Column Gas Chromatography (cont. )
Compounds Suggested Stationary Phase
- Hydrocarbons
Ci - C3 Carbowax 400 - Carbowax 1500, Proplyene Carbonate,
Tributylophosphate Didecylphalate
,
c - c * Carbowax 20M, SE-30, Squalane
Aromatics Tetracyanoethylatedpentaerythritol, DNP, Liquid

Crystalline Phases (such as Cyanobiphenyls,
Cholesterics)
- Ketones Lexan, FFAP, Carbowax 20M
- Nitriles FFAP, XF-1150
- Organometallics** FFAP, SE-30 (lower temperatures)
- Phosphorous Compounds SE-30, STAP
- Silanes SF-96, STAP
- Sulfur Compounds Carbowax 20M, FFAP, DNP, Solid Absorbents
* - consider a capillary column
** - consider HPLC
34
Silicone Liquid Phases
The following table lists the chromatographic properties of some of the
more popular polysiloxane based liquid phases [1-8]. The polysiloxanes are
the most widely used stationary phases in gas chromatography, and are
especially applicable to capillary columns. The listing provided here is far
from exhaustive. Since it is impractical to present the structures of all
polysiloxane-based phases, the OV phases have been chosen as representatives
since their properties are among the most well characterized. The phases
which are listed in the notes as "similar phases" have thermal and
chromatographic properties which are similar to the phase described.
The McReynolds constants are indices with respect to the following test
probe compounds:
McReyno Ids Test

Consta nt Probe
1 benzene
2 1-butanol
3 2-pentanone
4 1-nitropropane
5 pyridine
6 2-methyl-2-pentanol
7 1-iodobutane
8 2-octyne
9 1 ,4-dioxane
10 cis-hydrindane
The use of these constants is described in the previous table
35
Solvents
Ace - acetone Chlor - chloroform
Tol - toluene
Note : denotes a phenyl group in a structure.
REFERENCES :
[1] Yancey, J.A. , J. Chromatogr. Sci., 23, 161, 1985.
[2] McReynolds, W.O., J. Chromatogr. Sci., 8, 685, 1970.
[3] Mann, J.R. , Preston, S.T., J. Chromatogr. Sci., 11, 216, 1973.
[4] Trash, C.R., J. Chromatogr. Sci., 11, 196, 1973.
[5] McNair, H.M. , Bonelli, E.J., Basic Gas Chromatography , Varian Aerograph.
Palo Alto, 1969.
[6] Heftmann, E., Chromatography: A Laboratory Handbook of Chromatographic
and Electrophoretic Methods , 3rd ed.. Van Nostrand Reinhold, New York,
1975.
[7] Grant, D.W., Gas Liquid Chromatography , Van Nostrand Reinhold, London,
1971.
[8] Coleman, A.E., J. Chromatogr. Sci., 11, 198, 1973.
36
I
CNI in
I CO in
00
o
CN
00 en en CM
CM CM -J- (7^
w
d
C3^ 00 CO
CO
CO O
a
o
o vO eg m O
w
en in O
T3
O lO CN en 00 00 00
a 00 CM
C3^
Csl 1—1
CM
CO iT) in
00
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in un 00
o csl
o
p
OJ
> o o u u u
1—1
o
< < . rH >.^ >M-(
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CO 4-) CO 4-> CO +J CO
I— OJ r-H (U i-H QJ r-t
S >. E >. s >.
73 ^ P XI r-i x: ^ x:
- 4-> O
^
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I I 1 1
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T3 00 O T3 i^-i
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38
00
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39
1I 1(
11 I I 1 I
CN <t 00 lO
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w
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p
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X LO LO LO in LO
CO CO CO CO CO
s
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•H OJ >. u CM >, (U LO >. XI -H > XI -H > •iH -r-l >• 'H -H
hJ CM o OiT) O Ph-O o T3 W O "O w
40
!-i
(0
r-H
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W
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4-» Id
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T3 r-l C i-H fl d O d o
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ftT3
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41
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CO CO
00 00
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CM in in in
4-1
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CO oo
M
c
o <f CM 00
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W
T)
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c
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cri TO 1 m s I -H 4-1 I -H 4-1 1 •H 4-1
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o O 73 O -U S O -u E O Hi E
42
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I-H o
1+^ <f o
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acn
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0) u >> CI a
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ft fto
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S-i i-H i-lw 5h W !h W
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1
r— a 
1
e
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o U T3 O +J S O 4-) S o S 00
43
(
I
I 1 <1
CM
m
o
in
OO
c
CM
4-> (N
w
C
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u o 00
CsJ
w
r—
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O
OS CN
00
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CO CO CO
cn 00
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CM
CM 00
c 0)
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Csl c x: x: CM >. •H w
1 TO 4J 4-1 u 1—1 X
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1
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44
cu
c:
o
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1
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5^ O t\3 !-i rH 4J
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<N Oi ft U w S-i
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m
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rn
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ro III
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CO
3
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o o
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45
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00
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to CO
o
o o
CM
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3 W W CO
cr (15 X X
•w jn OJ
1^ a^ Q Q
46
1 t1 * 1 1
1 u ^ . >^ S^ >. u
xl 1— TO JS TO Oi
^-) o o +J o U
OJ Cu <v u
E o o e o
(U u J-» I— 1—1 4J r-H
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QJ >>
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TO
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<JJ
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CJ W w !-l U U W U
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— —X
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o
c_). en i—i TO CJ CJ en I— XI
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en
I
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CJ
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II
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1
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X CQ
X X f— U
CJ PQ i)
J h*w e
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u u
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< o o
o o o o
o o
4-» O CM \0 On OsJ
o
o
<!
T3 1—
•H (U •H •H
3 w W CQ
cr TO X X
•H XI OJ
hJ cu Q o
47
Adsorbents for Gas-Solid Chromatography
The following table lists the more common adsorbents used in gas-solid
chromatography, along with relevant information on separation and tech-
nique [1-3]. They are used chiefly for the analysis of gaseous mixtures. The
maximum temperatures listed represent the point of severe resolution loss. The
materials are chemically stable to much higher temperatures. The 60-100 mesh
sizes are most useful for chromatographic applications. All of these materials
must be activated before being used, and the degree of activation will influence
the retention behavior. Due to surface adsorption of solutes, some
experimentation with temperature may be necessary to prevent tailing or to avoid
statistical correlation (or a propagating error) among replicate analyses 1^2.
REFERENCES ;
[1 ] Jeffery, P.G., Kipping, P. J., Gas Analysis by Gas Chromatography , Pergamon

Press, Oxford, 1972.
[2] Cowper, C.J., DeRose, A. J., The Analysis of Gases by Chromatography ,
Pergamon Press, Oxford, 1983.
[3] Breck, D.W., Zeolite Molecular Sieves , John Wiley and Sons, New York, 1973-
[4] Bruno, T.J., J. Res. Nat. Bur. Stds. (U.S.), 90(2), 1127, 1985.
48
Maximum
Packing Temperature
Name °C Separation Effected Notes
silica 300 H2, Air, CO, Ci to C4 normal used often as a second column (with
gel hydrocarbons, alkenes and a molecular sieve); very hydrophil-
alkynes ic; requires activation; can be un-
predictable; largely replaced by
porous polymers.
porous 300 Same as silica gel higher surface area than silica gel;
silica often used with a humidified carrier
gas; can be coated with a conven-
tional liquid; Spherosil and Porasil
are examples.
alumina 300 light hydrocarbons at ambi- often useful with controlled water-
ent temperature (Ci to C5) preadsorption after activation; can
H2 and light hydrocarbons at be coated with a conventional liquid
subambient temperature phase.
activated 300 H2, CO, CO 2, Ci to C3 requires oxygen-free carrier gas;

carbon alkanes, alkenes and largely replaced by porous polymers.
alkynes
graphite 300 light hydrocarbons, H2S, often modified with small quantities
SO2, CH3SH, sour gas (1.5-555) of conventional liquid
phases; requires oxygen-free carrier.
carbon 300 H2 (O2, N2 co-elute), CO, high affinity for hydrocarbons; re-
molecular CH^, H2O, CO2, Ci to C3 quires oxygen-free carrier.
sieve alkanes, alkenes, alkynes
molecular 225 air and light gas analysis; synthetic calcium alumino-silicate
sieve, 5A H2, O2, N2, (CH^, CO, NO, (zeolite) having an effective pore
SFg co-elute) diameter of 5A; CO2 is adsorbed
strongly; 5A usually gives the best
results of all synthetic zeolites;
should be activated before use, and
used above critical adsorption tem-
perature; 21.6% (wt/wt) water capa-
city.
49
Maximum
Packing Temperature
Name °C Separation Effected Notes
molecular 200 same as 5A, but with C^ to sodium alumino-silicate (zeolite),

sieve, 13X C^ alkanes, alkenes, and having a larger pore size than 5A,
alkynes being separated as thus producing lower retention times
well and less resolution; 28.655 (wt/wt)
water capacity.
molecular 200 light permanent gases potassium alumino-silicate (zeolite);

sieve, 3A 20? (wt/wt) water capacity, smaller
pore size than 5A, thus different
retention characteristics.
molecular 200 light permanent gases sodium alumino-silicate (zeolite);

sieve, 4A 22/5 (wt/wt) water capacity; reten-
tion characteristics differ from
5A due to smaller pore size.
50
Porous Polymer Phases
Porous polymer phases, first reported by Mollis [1 ], are of great value
for a wide variety of separations. They are usually white in color, but may
darken during use at higher temperatures. This darkening does not effect
their performance. High temperature conditioning is required to drive off
solvent and residual monomer. The polymers may either swell or shrink with
heating; thus flow rate changes must be anticipated. The retention indices
(c) reported here are from the work of Dave [2]:
Index Test Probe
w Benzene
X t-butanol
Y 2-butanone
Z acetonitrile
The physical property data were taken from the work of Poole and Schuette [3]^
References:
[1] Mollis, O.L., Anal. Chem., 38, 309, 1966.
[2] Dave, S., J. Chromatogr. Sci., 7, 389, 1969.
[3] Poole, C.F., Schuette, S.A., Contemporary Practice of Chromatography ,
51
Packing Maximum Material Free Fall Surface Pore
Name Temperature Type Density Area Diameter
°C Av. ,\jm
Chromosorb 275 styrene- 0.30 <50 0.3-0.4

101 divinylbenzene
copolymer
Chromosorb 250 styrene- 0.29 300-500 0.0085

102 divinylbenzene
copolymer
Chromosorb 275 polystyrene 0.32 15-25 0.3-0.4

103 cross-linked
Chromosorb 250 acrylonitrile 0.32 100-200 0.06-0.08

104 divinylbenzene
copolymer
Chromosorb 250 acrylic ester 0.34 600-700 0.04-0.06

105 (polyaromatic)
52
, ,
Packing Retention Indices Separation effected Notes
Name W X Y Z
Chromosorb 745 565 645 580 free fatty acids, hydrophobic, condition
101 glycols, alcohols at 250°C; not recom-
alkanes, esters, mended for amines or
aldehydes ketones
, anilines lower
,
ethers retention times than

obtained with
Chromosorb 102
Chromosorb 650 525 570 460 subambient temperature: may entrain some
102 H2, O2, N2, Ar, NO, CO; species; hydrophobic;
Ambient temperature: condition at 225°C; not
H2, (Air + Ar + NO + recommended for amines
CO), CH4, CO2, H2O, or nitriles; little
N2O, CgHg; Above tailing of water or
ambient temperature: oxygenated hydro-
C1-C4 hydrocarbons, carbons
H2S, COS, SO2 esters,
,
ethers, alcohols,
ketones, aldehydes,
glycols
Chromosorb 720 575 640 565 ammonia, light amines, hydrophobic; high
103 light amides, alcohols, affinity for basic
aldehydes, hydrazines species; not recom-
mended for acidic
species, glycols,
nitriles, nitro
alkanes
Chromosorb 845 735 860 885 sulfur gases, ammonia, hydrophobic; condition
104 nitrogen oxides, at 225°C; not recom-
nitriles, nitroalkanes mended for glycols and
xylenols, water in amines; moderately
benzene polar
Chromosorb 635 545 580 480 permanent and light hydrophobic; less
105 hydrocarbon gases; polar than Chromosorb
aqueous solutions of 104; condition at
light organics such 225°C; not recommended
as formalin for acidic species,
glycols, amines and
amides
53
,

Av ,\^m
.
Chromosorb 250 polystyrene 0.28 700-800 0.05

106 cross-linked
Chromosorb 250 acrylic ester, 0.30 400-500 0.8

107 cross-linked
Chromosorb 250 acrylic ester, 0.30 100-200 0.25

108 cross-linked
Porapak-Q 250 ethylvinylben- 0.35 500-700 0.0075

zene-divinyl
benzene copolymer
Porapak-P 250 styrene-divinyl 0.28 100-200

benzene copolymer
Porapak-N 200 vinylpyrolidone 0.39 225-350
Porapak-R 250 vinylpyrolidone 0.33 300-450 0.0076
54
Name W X Y Z
Chromosorb 605 505 540 405 fatty acids from fatty hydrophobic, not recom-
106 alcohols, up to C5; mended for glycols and
benzene from nonpolar amines
organic compounds
Chromosorb 660 620 650 550 aqueous solutions of hydrophobic; moderately

107 formaldehyde; alkynes polar; not recommended
from alkanes for glycols and amines
Chromosorb 710 645 675 605 polar materials such hydrophobic; condition
108 as water, alcohols, at 250°C
aldehydes, glycols
Porapak-Q 630 538 580 450 similar to Chromosorb similar to Chromosorb

102 102; condition at 250°C
Porapak-P 765 560 650 590 similar to Porapak-Q hydrophobic; low

polarity; larger pore
size than Porapak-Q,
thus lower retention
times are observed;
not recommended for
amines or anilines;
condition at 250°C
Porapak-N 735 605 705 595 similar to Chromosorb condition at 175°; not
105; high water recommended for
retention; CO2 NH3,
, glycols, amines, or
H2O, C2H2 from
, acidic species
light hydrocarbons
Porapak-R 645 545 580 455 ethers, esters, H2O moderately polar;
from chlorine gases condition at 250°C; not
(HCl, CI2) nitriles recommended for glycols
and nitroalkanes and amines
55
°C g/cm^ m^/g Av. ,[Jm
Porapak-S 250 vinyl pyridine 0.35 300-450 0.0076
Porapak-T 200 ethylene glycol- 0.44 250-300 0.009

dime tha cry late
Porapak-QS 250 ethylvinylben-

zene-divinyl-
benzene copolymer
Porapak-PS 250 styrene-divinyl-

benzene copolymer
Tenax 375 p-2,6 diphenyl- 0.37 18.6

phenylene oxide
polymer
56
Name W X Y Z
Porapak-S 645 550 575 465 normal and branched high polarity; not
alcohols, aldehydes, recommended for acidic
ketones, halocarbons species and amines,
condition at 250°C
Porapak-T 675 700 635 water in formalin condition at 180°C;

(and other aqueous highest polarity of
organic mixtures), Porapak series; not
retention charac- recommended for glycols
teristics similar and amines
to Chromosorb 107
Porapak-QS 625 525 565 445 similar to Porapak-Q silanized Porapak-Q,

reduces tailing of
high polarity
compounds; condition
at 250°C
Porapak-PS similar to Porapak-P silanized Porapak-P,

condition at 250°C
Tenax similar to Porapak-Q highest thermal

stability of all
porous polymers
57
.
Cryogens for Subambient Temperature Gas Chromatography
The following table lists properties of common cryogenic fluids used to
produce subambient temperatures for gas chromatographic columns [1-4], These
properties are of value in designing low temperature chromatographic
experiments efficiently and safely. Due to the potential dangers in handling
extremely low temperatures and high pressures, appropriate precautions must be
observed
REFERENCES :
[1 ] Zabv^takis, M. G., Safety with Cryogenic Fluids , Plenum Press, New York,
1967.
[2] Cook, G. A., ed .

Argon,
, Helium and the Rare Gases , John Wiley & Sons
(Interscience ) New York, 1961.
[3] Brettell, T. A., Grob, R. L. , Am. Laboratory, 17 (10), 19, 1985.
[4] Cowpe'",C. J., DeRose, A. J., The Analysis of Gases by Chromatography ,
Perganon Press Oxford, 1983.

o
r-4
.—1
expansion
ratio o
CJ^
o
CO
in
CO
Liquid/Gas
CO CO
s
o
i-
Q-i
C3>
Critical
Temperature
CM co' CM
°C CY-l CO
1 CM
T 1 1 1
Cv
CTn CO '^ t^
(15.6°C) (15.6°C)
CO
. <o
^ .
cn
Heat
Capacity,
J/kg.K 638.06
1686.99 cn
^
.
LTi
00
cn CM
^ ^
^ .
LPl
LTi
cn V-
cn -^
Cp
CO o (15.6°C) v£5
CO
^-^
00
cn
•^
^--
. . . .
Heat
Capacity,
J/kg-K
2205.39 LPi cn ^ cn ^
cn LTi ^ ^
<\J CM CM CM CM
oo ^ CM --^
in
in
>>l
JJ O
^
^
^ o
•rH »— CO vo :g- vo
(0 X o CM CM t^ LPi CJN
.
o to
^' CM ^ CM CM CM CM CM ^ CM
CO •
•H CO
> a,
^
CY-I ^^ 00 ^
O
T— o
=r
°
'S
1—
LPl ^
^
CM CM S-,
^
Conductivity
^
Thermal
o o • CM . ^^ rH M
3
-p
w/m-K
CD --- CO
> > ^
^ ^ CD
i-H rH Cl.
B
> >
-P 4^
c C 4->
CD c
Pressure
CM
I^-
O
o •H
Vapor (MPa) S- t.
* * * * * CD d) £1
in CM Ci cx
CO
IP ,—
4->
T 1 CO
LP LP
rH
°C CM cd
5 .. •H
CY^ LO LPl CO CO .p
CO CO CO \o -p •H
Boiling
CM •rH i^
Point, 1 1 1 1 1 1 e .•
•rH c i-
rH
• bn Q.
>, iU >, D
-P •H X CO
•H a:
c r— CO
cu
"0 c •rH -rH
bO CD JD
o e C c bO s CO a
>. cO CO c f; •H
o
Dioxide x: ^ faO L
2
CM •H
^ X
CO D
Carbon
CO2
P X >. CM bO i, -P
CD X ClH
5: < 2 X *
59
Some Useful Fluids for
Supercritical Fluid Chromatography
The following table lists some useful carrier fluids for supercritical
fluid chromatography, along with relevant critical properties [1]. These
fluids have either been used or proposed for use in supercritical fluid
chromatography or supercritical extraction.
Fluid Tc(°C) Pc (g/mL) Pc (MPa)
Carbon Dioxide 31 .3 0.460 7.4
Ammonia 132.3 0.235 11.3
Nitrous Oxide 36.5 0.450 7.2
Sulfur Dioxide 157.5 0.520 7.9
Water 374.4 0.40 23.0
Methanol 240.5 0.272 8.0
Isopropanol 235.3 0.273 4.8
n-?entane 196.6 0.232 3.4
n-Hexane 23*^.2 0.234 3.0
D i chl or of luorom ethane 178.5 0.522 5.2
Trichlorofluoromethane 196.6 0.554 4.2
Chlorotr if luorom ethane 28.8 0.578 4.0
dichlorotetrafluoroethane 146.1 0.582 3.6
dichlorodifluoromethane 111.7 0.558 4.0
Benzene 288.9 0.304 4.9
Xenon 16.6 1.155 5.9
Toluene 320.8 0.29 4.2
[1 ] Bruno, T.J., Proc. 2nd Symp. Energy Engineering Sciences, 81, 1984,
60
II. Tables for Liquid
Chromatography
61
Solvents for Liquid Chromatography
The following table provides the important physical properties for the
selection of solvent systems for high performance liquid chromatography (HPLC)
[1-5]. These properties are required for proper detector selection, and the
prediction of expected column pressure gradients. The values of dielectric
constant aid in estimating the relative solubilities of solutes and other
solvents.
REFERENCES ;
[1] Willard, H.H., Merritt, L.L., Dean, J. A., Settle, F.A., Instrumental
Methods of Analysis 6^'^ ed., Wadsworth Publishing Co., Belmont, 1981.
,
[2] Snyder, L.R., Kirkland, J. J., Introduction to Modern Liquid

Chromatography ,
2'^'^ ed., John Wiley and Sons (Interscience) , New York,
1979.
[3] Dreisbach, R.R., Physical Properties of Chemical Compounds Number 22 of ,
the Advances in Chemistry Series, American Chemical Society, Washington

D.C., 1959.
[4] Krstulovic, A.M., Brown, P.R., Reverse Phase High Performance Liquid
Chromatography John VJiley and Sons (Interscience), New York, 1982.
,
[5] Weast R.C., Handbook of Chemistry and Physics , es'"*^ ed., CRC Press, Boca
Raton, 1983.
63
Viscos ity uv Refractive Boiling Dielectric
Solvent mN'sec /m^ Cutoff Index Point Constant
(20° C) nm 20 °C °C (20°C)
acetic acid ^ 15) 1.372 117.9 6.2

1 .31
acetone 0.30^ 25) 330 1.359 56.3 20.7 ^^')

acetonitrile 0.34^ 25) 190 1.344 81.6 37.5
benzene 0.65 278 1.501 80.1 2.284
1 -butanol 2.95 215 1.399 117.7 17.8
2-butanol 4.21 260 1.397 99.6 15.8 (^=)
n-butyl acetate 0.73 254 1.394 126.1
butyl chloride 0.47^ :0 220 1 .402 78.4

carbon tetrachloride 0.97 263 1.460 76.8 2.238
chlorobenzene 0.80 287 1.525 131 .7 2.708
chloroform 0.58 245 1.446 61 .2 4.806
cyclohexane 0.98 200 1.426 80.7 2.023
cyclopentane 0.44 200 1.406 49.3 1.965
o-di chlorobenzene 1.32^ 25) 295 1 .551 180.5 9.93 ^^^^
n,n-dimethylacetamide 2.14 268 1.438 166.1 37.8

dimethylformamide 0.92 268 1.430 153.0 36.7
dimethyl sulfoxide 2.20 286 1.478 189.0 4.7
dioxane 1.44^ 15) 215 1.422 101 .3 2.209 ^^'^
2-ethoxyethanol 2.05 210 1.408 135.6
ethyl acetate 0.46 256 1.372 77.1 6.02 ^2=)
ethyl ether 0.24 218 1.352 34.6 4.335
glyme (ethylene glycol 0.46^ 25) 220 1.380 93.0
dimethyl ether) i
heptane 0.42 200 1.388 98.4 1 .92
hexadecane 3.34 200 1 1 .434 287.0

hexane 0.31 200 1.375 68.7 1 .890
isobutyl alcohol 4.70^ 15) 220 1.396 107.7 15.8 (^')

methanol 0.55 205 1 .328 64.7 32.63 ^^=)
2-methoxyethanol 1 .72 210 1

1 .402 124.6 16.9
2-methoxyethyl acetate 254 1.402 144.5
64
Viscosity uv 1 Refractive Boiling Dielectric
Solvent mN«sec/m^ Cutoff Index Point Constant
(20°C) nm 20 °C °C (20°C)
methylene chloride 0.45^^') 233 1 .424 39.8 9.08

methyl ethyl ketone 0.42(^') 329 1.379 79.6 18.5
methyl isocimyl ketone 330 1 .406 -144.0
methyl isobutyl ketone 0.54(25) 334 1 1.396 1 16.5
N-methyl-2- pyrrol i done 1.67('') 285 1

1.488 202.0 32.0
nonane 0.72 200 1 1.405 150.8 1.972
pentane 0.24 200 1.357 36.1 1.84
petroleum ether 0.30 226 1

30-60
6-phenethyl amine 285 1

1.529(25) 197-198
1
-propanol 2.26 210 1
1.386 97.2 20.1 (^0
2-propanol 2.86(»^) 205 1 1.377 82.3 18.3 ^'')
propylene carbonate 1.419 240.0
pyridine 0.95 330 1.510 115.3 12.3 ^"^
tetrachloroethylene 0.93(10 295 1.506 121 .2
tetrahydrof uran 0.55 212 1

1.407 66.0 7.6
tetramethyl urea 265 1.449(20 175.2 23.0
toluene 0.59 284 1 1.497 110.6 2.379 (")
trichloroethylene 3.4 (is)
0.57 273 1.477 87.2
1 ,2,2-trichloro-1 ,2,2-
trif luoroethane 0.71 231 1.356(") 47.6
2,2, 4-trimethylpentane 0.50 215 1.391 99.2
water 1.00 <190 1
1.333 100.0 80.0
o- xylene 0.81 288 1.505 144.4 2.568
p-xylene 290 1 .5004 138.5 2.270
65
Modes of Liquid Chromatography
The following flow chart provides a rough guide among the various liquid
chromatographic techniques, based on sample properties [1].
Low
polarity
Reverse phase,
Aqueous mobile phase
Nonionic
Medium high
polarity
Liquid, solid, or
bonded phase
MW < 2000
Acidic
Anion exchange/ion pair
Ionic
Sample Basic
Cation exchange/ion pair
Water soluble
Steric exclusion,
Aqueous mobile phase
MW > 2000
Water insoluble
Steric exclusion.
Nonaqueous mobile phase
[1 ] Courtesy of Millipore Corporation, Waters Chromatography Division,
66
Reverse Phase Materials and Solvents
The following chart provides a rough guide to basic solvent systems for
bonded reverse phase packings [1]. These packings are the most widely used in
high performance liquid chromatography.
Sample Column packing Mobile phase
Low/moderate polarity Bonded C- 18 Methanol/ water

(soluble in
aliphatic
hydrocarbons)
Moderate polarity Bonded C-8 Acetonitrile/water

(soluble in
methyl ethyl
ketone)
High polarity Bonded C-2 1 ,4-Dioxane/water

(soluble in
lower alcohols)
[1 ] Reprinted with permission from: Willard, H.H., Merritt, L.L., Dean,

J. A., Settle, F.A., Instrumental Methods of Analysis 6^^ ed., Wadsworth
,
Publishing Co., Belmont, 1981.
67
HPLC Column Packings
The following table provides a summary of the general characteristics of
the more popular stationary phases used in modern high performance liquid
chromatography [I-3]. The most commonly used phases are the bonded reverse
phase materials, in which separation control is a function of the mobile
(liquid) phase. The selection of a particular phase and solvent system is an
empirical procedure involving survey analyses. The references provided below
will assist the reader in this procedure.
REFERENCES
[1 ] Snyder, L.R., Kirkland, J. J.,Introduction to Modern Liquid

Chromatography ,
2^^^ ed., John Wiley and Sons, New York, 1979.
[2] Poole, C.F., Schuette, S.A., Contemporary Practice of Chromatography ,
[3] Krstulovic, A.M., Brown, P.R., Reverse-Phase High Performance Liquid

Chromatography, John Wiley and Sons Interscience) New York, 1982.
( ,
68
1 1 1 1 1 1
•o -o
c CO
CO CO
•• •H rH
3 £1 to C^H-H
L TD CX o O i. •H JD
c -p H O •
a o c
X3 .— 1
-a ci_, CO O E •H
S O -P i—i • c H C E
D CO Cm -.H CO o CO CO -0 c o TD .O
•- C <i-i O X3 o •iH o >> .p •
X3 t. o •iH -p o i^ -a pp -p >. CO -P
CO C D CO E Jj CO -P C CO •H x: 3 CO
CD -H C CO ---1 CO o ^bO > > cx 3
x: CO •t-t •i-H -P 3 E H -H to rH E
Q. CO O "O x: 5- .— O CO E a -p -p i- CD
x: -H -p cx o c O -H bO •H Xcx
o CO +j o p cx cx i, o CO CO o t,
r-l C -P CO o o CO CO O ^ c 4-J
•^ r-l C p> CO H-l tn CO to 4J1 •-
CO £> t- 3 -rH O t- o i- CO CO E CO
c O CO -rH ^•^ cO c M -p o>. •
o E rH
o g Cn CO -P CO x: to x: 3 o x: CO CO S- .o
iH Q-i i. c o -P C
t^H x: -p CO o x: C -H .
J-> i. -rH O o
bO CO •rH •rH •H o O CO I>-
CO CO -O •- C CO •l-l o 3 CO .- o 3 -H f— E CO
o r— 1 CO CO 4J o -.H 3 CO 1— •iH c E o -a
f-l O C Q. x: !L CO CO Jj •o c CO 4-> •- GO o o cx c
,—t Q. O 3 O O s_ Cn CO .- o 3 CD rH O CO
Cl c o -p L. -.H f-t t- -H c £1 O c CO c
ex O "O S^ O J- c 3 i- cpi CO jJ •H •H CD 3 •P O C\J
< C bO jj CO •H f— 1 CO CD " .— x: I—i
o
CO •H
O -P c
CO jj o -p •o O L. -p -H p>
a x: CO i. CO c r— o O cx CO c CO 00 X S r-^3
c jJ) iD CO 3 3 o o to E cx o CO CO .
to •^ 1— TO o i- t^ >> a x: o O 3 I>-
^
1 1
S CO O -p to CO CO cx -P •H C CO pi
CO — CX C 3 c x: •H x: x: •p N CD TD
O
1
.-HO o o o bO o t. -p H •rH .-H i. -O C

-P >» Q-i JU .—1 o
.,-1 >5 •H 4-> •H CO o i- CO •H CD
O CO 4J O CO J-> c -P x: CO x: rH 3 CO x: -a
2 3 .^ jJ Q. c i^ -rH •H t- 3 o cx cx c rH bO
>, -H C
C\J
> C O L ^_^ •i-H > x: -o cx CO E •iH
>> -M O -M o -p i- • •H bO >> CO •H o x: •H c
.— -P -rH "O CO 4J CD to -p 3 x: >> L, rH to
rH O
1
4J> -O o ^ o o o o r-H M 3 -o • -P
CO tU CO L CO J2I •rH -H x: -Q cx CO Cw CO O
J
C 3
D ,-1 O cx TD s ^ M -p t^ E §3 jJ
H CD Jj •H 4_)
CO o c o o o •H .,H .—1 CD CO •M x: CO O Cu to
35 CO p-H D -P CO -p 00 CO 00 CD O CO X 3 cx 13 O X E -Q
CO
t^
1 CO T3 T3 o TD
CD >
C C c x: -o T3 -o a
o O o cx c c c c L
•iH •M •H o o o o
-U 4-> -P rH iD JH X3 X2 ••
CO -a CX cx CO TD
J- o S- L e i. CO i- CO i. CO t- CO CO
CO s: o o ^ CO CO to CO CO CD CO CD •O CD
a CO CO o -H x: -H x: p-H x: ^ X c x:
a a c o cx o cx o cx o cx o cx
00 <£. < tx a. &, Cu CQ
c 1
rH O -H
CO t, CD
c --ox:
o ex i-H >i O
—1 Z5 CM CM >. x:
4J O DC 2 X o o c
2 o o 2
1 1
O t- 1 1 O <o
c o 1 1 1 1 -O
CO O
-X2
L
D
Cx. -P CO 1
o c o
o
o1
o 1
1
•H O •H
00 GO
D
o
m 1
1
-H
o
1
o o
c cx C\J o oo o
o >.
CQ h-
o
iH
CM
M
1
•H H1
M 1 1
•H H1
t^
c/0 <c OO o OO OO 00 GO
en CO
^^ CO
C
^ T3
rH
-a -H •a o o
CO cx O L •H S_ c t. .— J-
sz >^ • M 3 e 3 O -H •O -P X3 O •a .p
Cu H ^ CX 3 cx C E C -H C -H C -H 00
•rH V_^ r— 1
O CD o c o -a o c Q
00 < CQ CQ CQ CQ o
69
1 1 1 11 11 1 1 1
.. x: 3
<D jj jJ O
CO o to -! x:
CO i. X3 sz 4->
x: o CL x: CO !*-, •-4
a. .. bO s x: CO -!-> O CO 3
CO L O —1 1-
a Cn bO CO •- 'r-i x: 3 •r^ C »
<D O C nH CO 3 •
i. cx CtH o >
o •.H CO O CO •-^ .-4 CO
C CO L
-i*: CO -a s S •' o 4-> i- to
O CD o o CO eCO O C x:
JD .^ (0 Ct^ x: CO J-) CO C — E -o cx
O D. cx zs CO C O 4-1 4J) C •
r-{ CD a >. O -^ to CO E >>

>, c:x c a •' CO — 1 E D t. 3 4J>
O CO CO CO CO JJ O O o • -4 tH
« CO a 4J 4-) C CO •O -H c >
o x: CO c CO C c =i c c O -4
CO CO> a c O CO rH - cr CO O E 4J
c j-i ,-1 1 o X2 x: > --H CO "O CO •r-^
E O
o o o -rH D. .— CO > 1 c to
o > o > C o x:
— O
• CO 1—1
.,-H CO -l-> s.
4-> c >> t. to 00 CO C 3 O •-H 4-> >5
03 cu -^ ^ S- x: s:
1
•a o c 4J> O t- CO
O x: •r-i > CO J-) f- s c to X3 to
•rH 4J CO i. cx o CO x: c t- c -o
.— c CO i, a CO C -tJ CO
-i-> to o £- C
D, c o r— CO c c s: •^ CO r-H ti-i a. 4J to
a CO •'-1 o ti-H CO CO Q. 3 x: o o 4->
<c x: 4J D. O E x: 4^ D. CO ^ c
jJ to >, -t-> OO 3 CO O
TD
C
i- 4J C
o >
o to CO -o j^ Ci-l • - -o 15 .-4
C CO C C >, i. C CO O CO cr 4.5
m O Cl CO -^ i- o - o c C CO c
.,-1 CD <L 1— 4J 3 C 00 > .-H -r-l CO CO O -^ •
CO -U CO •rH a CO Q 4J to E c •-1 cn x: 4J>
jj CD
D
.-H C
<i-,
ti-H
CO r— C
1— O
1
.^
o
o j_ to
O
-i->
-iJ
o
'f-i
C
CO
CO
c o
4-> 4J>
C-
z
o C O CD •rH >> CO i_ • —1 c a i- en 4J O o
CO CO x: TD x: O CO ll-H (0 c to >> to CO -4 Cw 4J 4J
i-H 3 4-:i C_ i:^-! cw x: CO >^ CO i- C^H C
-^ C >> .—1 4^ 4-3 .-H 4J 4J O t.
CO 1— 1— E 4J r-l3 r-H CO bO L c • CO •'-1 CO t.
.-H e 3 Jj (0 CO 3 O t. ^ CO i- C -a ^ C ,-H
>> c_ CO S- C^H s CO CO O CtH O CO to CO •^ Q-,
JJ 3 Jj 3 rH 3 i-^ Q. I. <Ui c -o cx bO to E <i-.
O O CO C O CO o o o o 4J 3 o x: x: •M —4
H -JDS
s-
O J =s bO J cx c OO CO X2 o to OO O Cl 00 TD
CO CO bO
J- t. CO c bO bO
to CO c C
> > x: x: to CO
c Q. o x: x:
o :_ i_ t. X o o
•iH O X X
-(-> <D •• » CO
CO -a •O a -H e c
L O CO CO CO o c c
CU S O CO T3 CO E > •r^ o o
Q. c sz c x: t- 4-> .-4 •rH
0) O Q. o cx O t, CO c c
CO CQ CQ 2 O cC cC
o >,
r— c -^ L
CO CD
O m O to E
c O Xi X < C 3 C\J
o ex
D
1 i- O O
L "-1 •-V
•M C CO C C^
P o o p. e -H 4J O X
o :-
o ^
o c r— 1 c ^ E o
c t. —1 >, o to E
D >^ -O CO x: Cw 3 CO 2
Cl, p >, x: O' 1
o x: o
o 00
» >1 tH
CO .—I CO CO CO
•O CD .-H
a
1
c
o >>
O o o •-H CO
3
O •-H r4
J-
1 1 1 i- 1 S-
CO E- rH •M i-H CO CO -^ cO CO
00 OO OO > 3 00 > >
CD
bO bO bO
0) c c c
CO <D .—1 to ca CO
CO O- >. x: x: x:
x: >^ c o o o
a- H CO C X C X C X
(^3 s: x: O O O
O ^ Cl. 1—1 h- HH
70
III. Tables for Ultraviolet
Spectrophotometry
71
Solvents for Ultraviolet Spectrophotometry
The following table lists some useful solvents for ultraviolet
spectrophotometry, along with their wavelength cutoffs and dielectric
constants [1-4].
REFERENCES :
[1 ] Willard, H.H., Merritt. L.L., Dean, J. A., Settle, F.A., Instrumental

Methods of Analysis 6 '^ ed., Wadsworth Publishing Co., Belmont, 1981.
,
[2] Weast, R.C., ed.. Handbook of Chemistry and Physics ,

63'"'^ ed., CRC Press,
Boca Raton, 1 983.
[3] Dreisbach, R.R., Physical Properties of Chemical Compounds Advances in ,
Chemistry Series, No. 15, American Chemical Society, Washington, D.C.,

1955.
[4] Dreisbach, R.R., Physical Properties of Chemical Compounds Advances in ,
Chemistry Series, No. 22, American Chemical Society, Washington, D.C.,

1959.
Wavelength Dielectric
Cutoff Constant
Solvent nm (20°C)
acetic acid 260 6.15

acetone 330 20.7 (25°C)
acetonitrile 190
benzene 280 2. 284
2-butanol 260 15.8 (25°C)

n-butyl acetate 25M
carbon disulfide 380 2.641
carbon tetrachloride 265 2.238

1 -chlorobutane 220 7.39 (25°C)
chloroform ''
245 4.806
cyclohexane 210 2.023
1 ,2-dichloroethane 226 10.19 (25°C)
1 - stabilized with ethanol to avoid phosgene formation
73
Cutoff Consi:ant
Solvent nm (20 'O
1 , 2-dimethoxyethane zno
N, N-dimethylacetamide 268 59 (83°C)
N, N-dimethylf ormamide 270
dimethyl sulfoxide 265
1 , 4-dioxane 215 2.209 (25°C)

diethyl ether 218 4.335
ethanol 210 24.30 (25°C)
2-ethoxyethanol 210
ethyl acetate 255 6.02 (25°C)

ethylene chloride 228
glycerol 207 42.5 (25°C)

n-hexadecane 200 2.06 (25°C)
n-hexane 210 1.890
methanol 210 32.63 (25°C)
2-met ho xy ethanol 210
methyl cyclohexane 210 2.02 (25°C)

methyl ethyl ketone 330 18.5
methyl isobutyl ketone 335
2-methyl-l -propanol 230 1
n- met hylpyrroli done 285
pentane 210 1.844

pentyl acetate 212
1 -propanol 210 20.1 (25°C)
2-propanol 210 18.3 (25°C)
pyridine 330 12.3 (25°C)
74
Cutoff Constant
Solvent nm (20°C)
tetrachloroethylene 2 290
tetrahydrofuran 220
toluene 286 2.379 (25°C)
1 , 1 ,2-trichloro-
1 ,2,2-trifluoroethane 231
2,2, 4-trimethylpentane 215 1.936 (25°C)

o-xylene 290 2.568
p-xylene 290 2.270
m-xylene 290 2.37M
water 78.54 (25°C)
2 - Stabilized with thymol (isopropyl meta-cresol)
75
Transmittance - Absorbance Conversion
The following is a conversion table for absorbance and transmittance.
Included for each pair is the percent error propagated into a measured
concentration (using the Beer-Lambert Law), assuming an uncertainty in
transmittance of ± 0.005 [1]. The value of transmittance which will give the
lowest percent error in concentration is O.368. Where possible, analyses
should be designed for the low error area.
REFERENCE:
[1 ] Kennedy, J. H. Analytical Chemistry Principles

, , Harcourt, Brace and
Jovanovich, San Diego, 1984.
Transmittance Absorbance Percent Error
0.990 0.004 50.227

0.980 0.009 25.242
0.970 0.013 16.915
0.960 0.018 12.752
0.950 0.022 10.256
0.940 0.027 8.592
0.930 0.032 7.405
0.920 0.036 6.515
0.910 0.041 5.823
0.900 0.046 5.270
0.890 0.051 4.818
0.880 0.056 4.442
0.870 0.060 4.125

0.860 0.065 3.853
0.850 0.071 3.618
0.840 0.076 3.412
0.830 0.081 3.231
76
0.820 0.086 3.071
0.810 0.091 2.928

0.800 0.097 2.799
0.790 0.102 2.684
0.780 0.108 2.579

0.770 0.113 2.483
0.760 0.1 19 2.396
0.750 0.125 2.316
0.740 0.131 2.243
0.730 0.137 2.175

0.720 0.143 2.1 13
0.710 0.149 2.055

0.700 0.155 2.002
0.690 0.161 1.952
0.680 0.167 1.906
0.670 0.174 1.863
0.660 0.180 1.822
0.650 0.187 1.785

0.640 0.194 1.750
0.630 0.201 1.717

0.620 0.208 1.686
0.610 0.215 1.657

0.600 0.222 1.631
0.590 0.229 1.605
0.580 0.237 1.582
0.570 0.244 1.560
0.560 0.252 1.539

0.550 0.260 1 .520
0.540 0.268 1.502
0.530 0.276 1.485
0.520 0.284 1.470
0.510 0.292 1.455
0.500 0.301 1.442
0.490 0.310 1.430
77
0.480 0.319 1.419

0.470 0.328 1.408
0.460 0.337 1.399
0.450 0.347 1.391
0.440 0.356 1.383
0.430 0.366 1.377

0.420 0.377 1.372
0.410 0.387 1 1.367
0.400 0.398 1.364
0.390 0.409 1.361
0.380 0.420 1.359

0.370 0.432 1.358
0.360 0.444 1.359
0.350 0.456 1.360
0.340 0.468 1.362
0.330 0.481 1.366
0.320 0.495 1.371
0.310 0.509 1.376

0.300 0.523 1.384
0.290 0.538 1.392
0.280 0.553 1 .402
0.270 0.569 1.414

0.260 0.585 1.427
0.250 0.602 1.442
0.240 0.620 1.459

0.230 0.638 1.478
0.220 0.657 1.500
0.210 0.678 1.525
0.200 0.699 1.553
0.190 0.721 1.584
0.180 0.745 1.619
0.170 0.769 1.659
0.160 0.796 1.704
0.150 0.824 1.756
78
O.UO 0.854 1.816

0.130 0.886 1.884
0.120 0.921 1.964
0.110 0.958 2.058
0.100 1.000 2.170
0.090 1.046 2. 306
0.080 1.097 2.473
0.070 1.155 2.685
0.060 1.222 2.961
0.050 1.301 3.336

0.040 1.398 3.881
0.030 1.523 4.751
0.020 1.699 6.387

0.010 2.000 10.852
79
Correlation Table for Ultraviolet Active Functionalities
Chromophore System ^Max ^Max Am ax ^Max Am ax ^Max
Ether -0- 185 1000
Thioether -s- 194 4600 215 1600
Amine -NH2- 195 2800
Thiol -SH 195 1400
Disulfide -s-s- 194 5500 255 400
Bromide -Br 208 300
Iodide -I 260 400
Nitrile -C=N 150
Acetylide -c=c- 175-180 6000
Sulfone -SO2- 180
Oxime -NOH 190 5000
Azido >C=N- 190 5000
Ethylene -c=c- 190 8000
Ketone >C=0 195 1000 270-285 18-30
Thioketone >C=S 205 strong
Esters -COOR 205 50
Aldehyde -CHO 210 strong 280-300 1 1-1
Carboxyl -COOH 200-210 50-70
Reprinted (with modifications) with permission from: Willard, H.H., Merritt, L.L.,
Dean, J. A., Settle, F.A., Instrumental Methods of Analysis 6^^^ ed., Wadsworth
,
Publishing Co. Belmont, 1981.

,
80
Chromophore System Am ax ^Max '^Max ^Max ^Ma) ^Max
Sulfoxide >S>0 210 1500

Nitro -N02 210 strong
Nitrite -ONO 220-230 1000-2000 300-4000 10
Azo -N=N- 285-400 3-25
Nitroso -N=0 302 100
Nitrate -ONO2 270 12
(shoulder )
-(C=C)2- 210-230 21 ,000
(acyclic)
-(0=03- 260 35,000
CO
s -(C=C)i|- 300 52,000
-(C=C)5- 330 118,000

00
n -(C=C)2- 230-260 3000-8000

<v
n3
3 (alicyclic)
'-)
C c=c-c=c 219 6500
o
o
C=C-C=N 220 23,000
c=c-c=o 210-250 10,000-20, 000 300-350 weak
C=C-N02 229 9500
Benzene 184 46,700 202 6900 255 170
Diphenyl 246 20,000
Naphthalene 220 112,000 275 5600 312 175
Anthracene 252 199,000 375 7900
Pyridine 174 80,000 195 6000 251 1700
81
Quinoline 227 37,000 270 3600 314 2750
Isoquinoline 218 80,000 266 4000 317 3500
Note: $ denotes a phenyl group.
82
IV. Tables for Infrared
Spectrophotometry
85
Infrared Optics Materials
The following table lists the more common materials used for optical
components (windows, prisms, etc.) in the infrared region of the
electromagnetic spectrum. The properties listed are needed to choose the
materials with optimal transmission characteristics [1,2]. The thermal
properties are useful when designing experiments for operation at elevated
temperatures [3,5]. This listing is far from being exhaustive, but these are
the most popular materials used in instrumentation laboratories.
REFERENCES:
[1 ] Gordon, A. J., The Chemist's Companion , John Wiley and Sons, New York,
1972.
[2] Willard, H. H. Merritt, L. L.

, Dean, J. A., Settle, F. A.,
, Instrumental
Methods of Analysis 6th ed., Van Nostrand, New York, 1985.
[3] Touloukien, Y. S., Powell, R. W., Ho, C. Y., Klemens, P. G.,

Thermophysical Properties of Matter: Thermal Conductivity of
Nonmetallic Solids Vol. 2, IF - Plenum Data Corp., New York, 1970.
[4] Touloukien, Y. S., Kirby, R. K. Taylor, R. E. Lee, T. Thermophysical

, ,
Properties of matter: Thermal Expansion of Nonmetallic Solids, Vol. 13 ,
IF - Plenum Data Corp. New York, 1977.
[5] Weast, R.C., ed. Handbook of Chemistry and Physics , 63rd. ed .

, CRC Press,
Boca Raton, 1
87
1 ' — — 1 1 — s 11
i ', — 1 X
. x: o o
.—1 >> o CO :H -.-1 bO
03 o3 -u> J^ CO CO CO CO C i.
—1 L - r— :_ 03 03 -1 o
s_ o CO cj> -P t. O .— C XI C XI c ^
Q-i C crs CO J-J Cw >H •t-H •rH •fH
-U O 2 CO E x: -P E x: -P 03 C
m .- •.H x: .— Q. 03 jj x: -P O
XI -^ x
1
E S_ J-> -o jj x: t, 3 •M bO "^.t^-a
D jJ CQ Ci-1
:- 3 -H j_ 3 - O -P CJ
n C -P .-1 -U CO .— o ^ O ^ D CO
S_ ^ -O
1
CD O 03 O Oi 03 L
O
O CO
3 E
G. '+H
o
CO Cl-H
a
CO
O O C C
bO
jj E 3 CO i. » - •-H
o E 3 c Cm 03 a — c > -o -< c > Ci_i CO CT3 -^ o
s o to CO jj O -iJ XI - CO O 3
1
-^ O 3 -^
— x: C
O X3 3 03 C •r-t ^ C O !3r bO -P O CT bO P> -H i, o
t. O CO JJ 3 o o -o K) -rH O -H bO -^ O --1 3 2 jP 3
J-^ o 3 > CUH Jj -M -nH rH J_ CO ^ i. CO C^-, ^ cr
CD CO D .-H .—1 fci2 ,— p P> c 4-> -PC bO - i_
O X3 CT CO o o CO Q-, O O i. -M O i, -M CO — X -P S-
S Oi 05 3 CO CO 3 O i- CO 2 O C CO 2 O C CO o x:
1
o CO C^-i
^-^ ^-N ^—^ ^-^ ,-— ^_^ ^_^ ^ ^ ^-x ,—^ ^— ^—. ^— ,— ,
^ isi ii: i=i i^: iii :^ i^ ii^ isi i^ ^ >^

•:^
o o o o o o o o o tn o O O O
o o o o o o tn
o o O CM IXi O O O
rH
c
O -U
^
^^-^
LO
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^r Ln ^D
^_^ >-_^ ^_-^
J3-
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^X5
v._^
cn
V ^
CO OO
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CD \CO i- :=r CO o =r CO on C-- .— O - - CM ^ ô
x: D. J CD . . • .
E- X O Q. o o o o o o o ^ o o o o o o
w
-'-~v ^-^ ^.^^ ^,_^ ^, ^ ,—V ^-v .-^

>, ^•^ ^ i^ ^ ii^ isi isi i^ i-^ ^~.
JJCXJ ,~v ,^^ .-^ ^-- Li^ Oi OO O LTi CM CM CM bi; ^^ --^
•.H o isi iii ii:: ^^ . . •
m
• • • • [>- ixi i^:
1—1 .^
>
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m o o
c— o o
in
c-
^
o
CM
c—
CT^
v£> ^
rg CO OO cn
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OO
CM
C7>
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CM
03 jJ — cv c^ .=r CM m on CM c>n
C--
cn m m ^T IT,
--' OO ^
e o i=d ^_^ ^^ N^^ V_^ N ^ S ^ ^^^ V ^ v^ y,.^^^ s ^ ^.^ V •
^ D •
o
CD "O
x: c \
s , — in , o tr~- o ^ O
C3> LO
^ o o c:!> ^ ^ o^
^ ^
^n \D CO O CX3 OO o> t— c— .
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o • •
o t>- v£) â- LPi ^3- ^3- o o o ^— o> ^3-
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;l
CD eg
>
-> Jj
JJ 03 CM oo o
a
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.
o CM
.
^=T
03 . .
^ T t CM CM T
Ci-i"O
c
CE 1—
S- >— o
0) LPi o 'S\
m yO
o o
1
X3 E CM CO
e o
D
^ 1
^r
1
^r
1
CM
1
t
c - O o o O <—
CD
M O o o o
o-
1
CD o o- o o
> C •• •>
I>-
03 03 o o in o vD
^
5 L ^T ^:t eg rg
x:
JJ E
bO 3- ^jD LO LO
C t CM cn OO o^
- 1 1 rg 1 1
,— 1 CD LTi
CM
li^ 1 o IXi
CD tiO CM ;=r Lf> ,
> C • • • ^ •
03 03 O O o o o
:3 S-
E
r^ D
nj a rH CD o E T3
3 -M N
•H E -M 1— CO -o i_ -rH r-l i, -a
L
-H O
:^ 5- o CO --H i-
> O
J- ObO >
— 1 S- •^
O O
i_ Cl,
E
^ EO
CD 03 03 cn CG 03 1
JJ -a ^. S j^ O i^ ,-H 1— 1 =£ bO ,-H 3 O
to o jr o a- -^ x: •M i. <£ 03 —
S CO o Q- X) CO o CO x: O Ci-i
handle TlBr,
a
handled
4J>
C-Br C-Br
4255 •iH
CO
CO sensitive, o
toxic,
for for
be
o care care;
-o
frequencies frequencies
Til E
stretching stretching 3
3
Shock
should
with
Useful Useful
Highly
with 5855
O
CO
>
iC •iC ^ (400K) (500K) (600K) (373K) (473K) (400K) (500K) (600K) (400K) (500K) (600K)
CD CD
CD CD CD
O
^ in ^
o-i ,- CO
percent
Expansion
en kO CTy
Thermal
AL/L
CM ^^ 0.526 1.063
.645
0.464 1.026 0.086 0.175 0.272 0.033 0.066 0.102
O CD CD 1
i^ i^ i^ 7K) 7K)
OK)
•=r in in
(284K) (305K) (370K)
CJ^ t- c~-
\D en^^ (277. (296. (360.
CM en en
Conductivity
^ O
Thermal W/m-K(X102)
v£>
11.7 10.9 10.5
CM o t- 1.15 1.05 9.50
C7> CO t-
2ym)
at
Refractive
en ^3- o in
CM CM en
Index
en
o o o O o
number cm"''
!>• o CO in
OO
kO
CO CM CM CM in
1 1 1 1 1 1
o o
1
O o o o o o
o
o O o o o
o
o
o
O o o o
Wave
range,
o O o o o o
CM
o
in
CM
in
ym in CM
in
en I
Wavelength
I o 1 CO T o
CM en in in in CM
T
range,
O
1 1
o O
t-H
CO c
•rH o
%~
Br-Tll
ZnSe
germanium
Ge
o
fluoride
bromide
thaliura
bromide thalium
selenide
—1 -.H
barium cesium CsBr cesium iodide iodide
4J BaFp Csl (KRS-5) r-l 00
zinc
CO rH
CO
Tl
89
many
for compounds
CO
<u
-p
o useful
organic
not
(400K) (500K) (600K)
percent
Expansion
Thermal
0.075 0.148 0.225
CM '^ CM
. bti •
on c^ CM
o CM on
CM m ::^
Conductivity
^
Thermal W/m-K(X102)
on CM
LTl ^ a-
CM CM ^
2ym)
at
^
Refractive 1.76
^
Index
number cm~^
50,000-1538
en
CM
625-33
1
range,
Wave
LTl
ym
Ln
CM
.=r
0.20-6.5
Wavelength
1 '
16-300
range,
CM
CD
c
f—l
i-H
OS (Sapphire)
sz
4-J
aluminum
AUO3
CD
(D oxide
mica
4-5
OS Q
cn.
90
WAVELENGTH-WAVENUMBER CONVERSION TABLE
Wavenuraber (cm-M
1 2 3 4 5 6 7 8 9
2.0 5000 4975 4950 4926 4902 4878 4854 4831 4808 4785
2.1 4762 4739 4717 4695 4673 4651 4630 4608 4587 4566
2.2 4545 4525 4505 4484 4464 4444 4425 4405 4386 4367
2.3 4348 4329 4310 4292 4274 4255 4237 4219 4202 4184
2.H 4167 4149 4232 4115 4098 4082 4065 4049 4032 4016
2.5 4000 3984 3968 4953 3937 3922 3006 3891 3875 3861
2.6 3846 3831 3817 3802 3788 3774 3759 3745 3731 3717
2.7 3704 3690 3676 3663 3650 3636 3623 3510 3597 3584
2.8 3571 3559 3546 3534 3521 3509 3497 3484 3472 3460
2.9 3448 3436 3425 3413 3401 3390 3378 3367 3356 3344
3.0 3333 3322 3311 3300 3289 3279 3268 3257 3247 3236
3.1 3226 3215 3205 3195 3185 3175 3165 3155 3145 3135
3.2 3125 3115 3106 3096 3086 3077 3067 3058 3049 3040
3.3 3030 3021 3012 3003 2994 2985 2976 2967 2959 2950
3.4 2941 2933 2924 2915 2907 2899 2890 2882 2874 2865
3.5 2857 2849 2841 2833 2825 2817 2809 2801 2793 2786
3.6 2778 2770 2762 2755 2747 2740 2732 2725 2717 2710
3.7 2703 2695 2688 2681 2674 2667 2660 2653 2646 2539
3.8 2632 2625 2618 2611 2604 2597 2591 2584 2577 2571
3.9 2654 2558 2551 2545 2538 2532 2525 2519 2513 2505
4.0 2500 2494 2488 2481 2475 2469 2463 2457 2451 2445
4.1 2439 2433 2427 2421 2415 2410 2404 2398 2387 2387
4.2 2381 2375 2370 2364 2358 2353 2347 2342 2336 2331
4.3 2326 2320 2315 2309 2304 2299 2294 2288 2283 2278
4.4 2273 2268 2262 2257 2252 2247 2242 2237 2232 2227
4.5 2222 2217 2212 2208 2203 2198 2193 2188 2183 2179
4.6 2174 2169 2165 2160 2155 2151 2146 2141 2137 2132
4.7 2128 2123 2119 2114 2110 2105 2101 2096 2092 2088
4.8 2083 2079 2075 2070 2066 2062 2058 2053 2049 2045
4.9 2041 2037 2033 2028 2024 2020 2016 2012 2008 2004
5.0 2000 1996 1992 1988 1984 1980 1976 1972 1959 1965
5.1 1961 1957 1953 1949 1946 1942 1938 1934 1931 1927
5.2 1923 1919 1916 1912 1908 1905 1901 1898 1894 1890
5.3 1887 1883 1880 1876 1873 1869 1866 1862 1859 1855
5.4 1852 1848 1845 1842 1838 1835 1832 1828 1825 1821
5.5 1818 1815 1812 1808 1805 1802 1799 1795 1792 1788
5.6 1786 1783 1779 1776 1773 1770 1767 1764 1751 1757
5.7 1754 1751 1748 1745 1742 1739 1736 1733 1730 1727
5.8 1724 1721 1718 1715 1712 1709 1706 1704 1701 1598
5.9 1695 1692 1689 1686 1684 1681 1678 1675 1672 1559
6.0 1667 1664 1661 1568 1656 1653 1650 1647 1645 1642
6.1 1639 1637 1634 1631 1629 1626 1623 1621 1518 1616
6.2 1613 1610 1608 1605 1603 1500 1597 1595 1592 1590
6.3 1587 1585 1582 1580 1577 1575 1572 1570 1557 1565
91
)
WAVELENGTH-WAVENUMBER CONVERSION TABLE
Wavenumber ( cm" ^
6.4 1563 1560 1558 1555 1553 1550 1548 1546 1543 1541
6.5 1538 1536 1534 1531 1529 1527 1524 1522 1520 1517
6.6 1515 1513 1511 1508 1506 1504 1502 1499 1497 1495
6.7 1493 1490 1488 1486 1484 1481 1479 1477 1475 1473
6.8 1471 1468 1466 1464 1462 1460 1458 1456 1453 1451
6.9 1449 1447 1445 1443 1441 1439 1437 1435 1433 1431
7.0 1429 1427 1425 1422 1420 1418 1416 1414 1412 1410
7.1 1408 1406 1404 1403 1401 1399 1397 1395 1393 1391
7.2 1389 1387 1385 1383 1381 1379 1377 1376 1374 1372
7.3 1370 1368 1366 1364 1362 1361 1359 1357 1355 1353
7.4 1351 1350 1348 1346 1344 1342 1340 1339 1337 1335
7.5 1333 1332 1330 1328 1326 1325 1323 1321 1319 1318
7.6 1316 1314 1312 1311 1309 1307 1305 1304 1302 1300
7.7 1299 1297 1295 1294 1292 1290 1289 1287 1285 1284
7.8 1282 1280 1279 1277 1276 1274 1272 1271 1269 1267
7.9 1266 1264 1263 1261 1259 1258 1256 1255 1253 1252
§ 8.0 1250 1248 1247 1245 1244 1242 1241 1239 1238 1236
^ 8.1 1235 1233 1232 1230 1229 1227 1225 1224 1222 1221
5 8.2 1220 1218 1217 1215 1214 1212 121 1 1209 1208 1206
^ 8.3 1205 1203 1202 1200 1199 1198 1196 1195 1193 1192
^ 8.4 1190 1189 1188 1186 1185 1183 1182 1181 1179 1178
^ 8.5 1176 1175 1174 1172 1171 1170 1168 1167 1166 1164
^ 8.6 1163 1161 1160 1159 1157 1156 1155 1153 1152 1151
8.7 1149 1148 1147 1145 1144 1143 1142 1140 1139 1138
8.8 1136 1135 1134 1133 1131 1130 1129 1127 1126 1125
8.9 1124 1122 1121 1120 1119 1117 1116 1115 1114 1112
9.0 1111 1110 1109 1107 1106 1105 1104 1103 1101 1100
9.1 1099 1098 1096 1095 1094 1093 1092 1091 1089 1088
9.2 1087 1086 1085 1083 1082 1081 1080 1079 1078 1076
9.3 1075 1074 1073 1072 1071 1070 1068 1067 1066 1065
9.4 1064 1063 1062 1060 1059 1058 1057 1056 1055 1054
9.5 1053 1052 1050 1049 1048 1047 1046 1045 1044 1043
9.6 1042 1041 1040 1038 1037 1036 1035 1034 1033 1032
9.7 1031 1030 1029 1028 1027 1026 1025 1024 1022 1021
9.8 1020 1019 1018 1017 1016 1015 1014 1013 1012 1011
9.9 1010 1009 1008 1007 1006 1005 1004 1003 1002 1001
10.0 1000 999 998 997 996 995 994 993 992 991
10.1 990 989 988 987 986 985 984 983 982 081
10.2 980 979 978 978 977 976 975 974 973 972
10.3 971 970 969 968 967 966 965 964 963 962
10.4 962 961 960 959 958 957 956 955 954 953
10.5 952 951 951 950 949 948 947 946 945 944
10.6 943 943 942 041 940 939 938 937 936 935
92
WAVELENGTH-WAVENUMBER CQIJVERSION TABLE
Wavenumber (cm-M
1 2 3 4 5 6 7 8 9
10.7 935 934 933 932 931 930 929 929 928 927
10.8 926 925 924 923 923 922 921 920 919 918
10.9 917 917 916 915 914 913 912 912 911 910
11.0 909 908 907 907 906 905 904 903 903 902
11.1 901 900 899 898 898 897 896 895 894 894
11.2 893 892 891 890 890 889 888 887 887 886
11.3 885 884 883 883 882 881 880 880 879 878
11. n 877 876 876 875 874 873 873 872 871 870
11.5 870 869 868 867 867 866 865 864 864 863
11.6 862 861 861 860 859 858 858 857 856 855
11.7 855 854 853 853 852 851 850 850 849 848
11.8 8M7 847 846 845 845 844 843 842 842 841
11.9 840 840 839 838 838 837 836 835 835 834
12.0 833 833 832 831 831 830 829 829 828 827
12.1 826 826 825 824 824 823 822 822 821 820
12.2 820 819 818 818 817 816 816 815 814 814
12.3 813 812 812 811 810 810 809 808 808 807
^2.i^ 806 806 805 805 804 803 803 802 801 801
12.5 800 799 799 798 797 797 796 796 795 794
12.6 794 793 792 792 791 791 790 789 789 788
12.7 787 787 786 786 785 784 784 783 782 782
12.8 781 781 780 779 779 778 778 777 776 776
12.9 775 775 774 773 773 772 772 771 770 770
13.0 769 769 768 767 767 766 766 765 765 764
13.1 763 763 762 762 761 760 760 759 759 758
13.2 758 757 756 756 755 755 754 754 753 752
13.3 752 751 751 750 750 749 749 748 747 747
^3.^ 746 746 745 745 744 743 743 742 742 741
13.5 741 740 740 739 739 738 737 737 736 736
13.6 735 735 734 734 733 733 732 732 731 730
13.7 730 729 729 728 728 727 727 726 726 725
13.8 725 724 724 723 723 722 722 721 720 720
13.9 719 719 718 718 717 717 716 716 715 715
U.O 714 714 713 713 712 712 711 711 710 710
U.I 709 709 708 708 707 707 706 706 705 705
1M.2 704 704 703 703 702 702 702 701 701 700
14.3 699 699 698 698 697 697 696 696 695 695
U.i4 694 694 693 693 693 692 692 691 691 690
U.5 690 689 689 688 688 687 687 686 686 685
U.6 685 684 684 684 683 683 682 682 681 681
U.7 680 680 679 679 678 678 678 677 677 676
U.8 676 675 675 674 674 673 673 672 672 672
U.9 671 671 670 670 669 669 668 668 668 667
93
Useful Solvents for Infrared
Spectrophotometry
The following tables provide the infrared absorption spectra of several
useful solvents. The spectra were measured using a double beam spectropho-
tometer using a neat sample against an air reference. The physical properties
listed are those needed most often in designing spectrophotometric
experiments [l-^]. The refractive indices are values measured with the
sodium-D line. The Chemical Abstract Service registry numbers are alos
provided for each solvent.
REFERENCES ;
[1 ] Hawley, G.G. ed., The Condensed Chemical Dictionary , Van Nostrand

Reinhold Co., New York, 1971.
[2] Weast, R.C., ed., Handbook of Chemistry and Physics ,

52"^ ed.. The
Chemical Rubber Co., Cleveland, 1971.
[3] Dreisbach, R.R., Physical Properties of Chemical Compounds, Advances in

Chemistry Series Number 22, American Chemical Society, Washington, D.C.,
,
1959.
[4] Jamieson, D.T., Irving, J.B., Tudhope, J.S., Liquid Thermal Conductivity
- a data survey to 1973, Her Majesty's Stationary Office, Edinburgh,
1975.
94
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The following tables provide expected IR absorptions of the major
chemical families [1-13].
Abbreviations:
s Strong
m Med i um
w Weak
vs Very strong
vw Very weak
sym Symmetrical
asym Asymmetrical
REFERENCES ;
[1 ] Nakanishi, K., Solomon, P.H., Infrared Absorption Spectroscopy ,
Holden-Day, Inc., San Francisco, 1977.
[2] Conley, R.T., Infrared Spectroscopy , 2nd edition, Allyn and Bacon,
Boston, 1972.
[3] Silverstein, R.M., Bassler, G.C., Morrill, T.C., Spectrometric

Identification of Organic Compounds John Wiley and Sons, New York, 1981.
,
[4] Williams, D.H., Fleming, I., Spectroscopic Methods in Organic Chemistry ,
McGraw-Hill, London, 1973.
[5] Kucsman, A., Ruff, F. , Kapovits, I., Tet .

, 22, 1575 (1966).
[6] Kucsman, A., Ruff, F. , Kapovits, I., Acta, Chim. Acad. Sci. Hung., 40, 75
(1964).
[7] Kucsman, A., Ruff, F. , Kapovits, I., Acta. Chim. Acad. Sci. Hung., 54,
153 (1967).
[8] Shah, J., Can. J. Chem., 53, 2381 (1975).
[9] Tsujihara, K., Furukawa, N. , Oae , S., Bull. Chem. Soc . Japan, 43, 2153
(1970).
[10] Lambert, J.B., Shuzvell, H.F., Verbit, L. Cooks, R.G., Stout, G.H., ,
Organic Structural Analysis MacMillam Pub. Co., New York, 1976.

,
[11] Fuson, N., Josien, M.L., Shelton, E.M., J. Am. Chem. Soc, 76, 2526,
1954.
[12] Meyers, C.Y., Eighth Annual Report on Research, 1963, Sponsored by the
Petroleum Research Fund, American Chemical Society, Washington, D.C.,
1964.
[13] Meyers, C.Y., Estratto dalla Gazzetta Chimica Italiana, 93, 1206, 1963.
115
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s).
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650,
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spectra
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(1 the
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X
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dilute to
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CD Organic
O
2 Nitrogen
pounds
See
x:
o or or
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i-
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CO
•o
o 1300-1175(s)
o
1
c 950-910(s)
bands) bands)
C
O
(J
two two
CO
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c
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c
e
o 1790
the
o frequencies
considerably
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raises
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1735-1715(m/s((sym)
and Conjugation
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o j->
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1850
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c II
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to
bO
o
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to ^
frequency
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to
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Cyclic
acylic
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03
Amides
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(i):
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C , CO -H O O '-^ C3^
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x:
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CO o
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s
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CO CO
1
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CO •rH
CO acids c X
CO o
(v): c.
o
126
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s:
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CD
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127
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128
CO
CD Compounds. Compounds.
o
II
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2
II
l660-l6lO(m)(>C=CC)
CJ
~1000(m),909(m)
/\
Organic Organic
CO
(>C=C-H)
Nitrogen Nitrogen
o
LTi
See See
1
trace
a
<D stretch
to
C 1075-1020(s) 1075-1020(s)
•H symmetrical
4-5
C
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CJ 1
s >C-0-C<
o
CO
very
c CO
D
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cx
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hO 3: to
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o stretch
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adjacent
off
asymmetrical
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c creates 1225-1200(s) CO CO CO CO
CO
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in on LH
CM UD cv-i
due due
o >C-0-C<
1150-1085(3) 1275-1200(3)
>- ^ o o
T T T T
branching
carbons
oxygen
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o in oo Lo
C7^ CTn LHC7^
T- r- C, O
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CO M rH M rH CM
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CE ^ >> C O " CC ^
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II
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C5 O
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cc 1
CC CC CC CC CC CC cc
alkyl
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CD
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CO •o o CO CD
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129
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1— CO rH +-)
l-l C) ^ 1 ^
s c
CO
Uu
o
>>
O
1
S w to
QQ
1
Jj
--^^
i>i; faO
131
I1 ' ^ V
^ — ^ V —— ^
1 —
S=
CO o o
0) .H c^
J-> c
o 03 c
2: bO n) •
J. bO CO
O o o
t. c
(D -1-) D
CD •rH o
00 2 D.
CO CO CO CO CO CO CO CO
^ jx: ^ js: ^
03 03 03 03 OS OS 03 OS
<V CD <D CD 0) 0) <D
a. a. CX Q. Q. ex D. en.
o
o o O o o o o o
0) 5 3 3 3 3 3 3 3
L j-3 4-5 -l-> 4J 4J jJ
CO CO CO CO CO CO CO CO CO
O o
LTi
O
LTi
O
LO
o o
in LTl
o
ITi
o
LTi
o
LO
O O O O o o O O O
I
I I
o o
I 1 1
o o o o CD o
o o o o o o O o
on on on on en m on on
CD
C
•f-i x:
•4-> o
c CO CO
o CD
CJ) o o
CO
^"^
CO
^~v
CO
CM
U3
^
LTi
CO >.-• '^—.^ T t
•o
o in o 1 1
c CO CO
VO
MD
vO
o
in
o t>-
O
Q.
CD o <— .— <0 LO
X3
e S
o 3
(j> C
CD
c > c
03
bO bO ^—
LTl O Jj
in t- CD
o I^ -n .—
X3
s: 1 3
o LPl 1
O
c CX3 s o
03 CD f— •k
bO '— c to
S_ 0)
^_^
O CO
— — ^^
JJ x: -p in
• V ,^-v ,' ,-
CD 3 c y— ^•— ,
o CO CO m
— CO CO ^ (D CO CO t—
II
^^.-^ >. -- ^. ^ V • n ^ CO •^w--' v_^ T
o LO o o o O 3 1 CD o o 1
/\ on tr- ^g- C\J LPi O id i. <D a^ •in

t- I>- co t^- t- •a
^"^
o a. C— f— r*
t-
T T T T Y Y J
>—X-o
M Oj C
03 — c •rH
L 3 o
CD S /
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C L ^-^ ^r on C\J ^^ cn .3- on >1 S
(D O '^ a. 3
^
I
O
,
\,
o^/
II II II II II 11 II II 1
s O
^— X X X X X X X X "
Ci) 1
x: 1 x: x: 3
T3 1 4-> t. 4-) 1 J-3 C
£- 3 J- -o
4-5 3 o -U o 3 o C bO
03 4-> 4J 03 4J jJ J-> 03 >,
S- 03 CO 03 X
3 CO 1 rH c 1 CO 1 rH O
CO jJ c 3 >5 3 a c s >5
1— CO a) 03 3 c .'^ c 3 C
•rH S c CO 1 1 1
- o o • • •»
o •>
x:
S 03 o <o >- ca •o XJ
• • ^-^ -o bD -o X3 4-)
o
II
03 jJ 4J .. ^-^ CD L 'j-\ >, ^— t.

U. o o ^-^ y-^ ,—^ ^^ ^ JJ m /^ •r-i -pX > -p 03 o
03 Oi -M 03 J2i o 03
'f-i o - •rH m o •rH 03 O -iJ
_J _J ^^ — ' ^^-^
132
CO Com- Com- Com- Com- Com-
4J
o Organic Organic Organic Organic Organic
2
Nitrogen Nitrogen Nitrogen Nitrogen Nitrogen
pounds. pounds. pounds. pounds. pounds.
See See See See See
o
0)
CO
o
o1
a>
3
C
•iH
o
c
o 0)
o 4-3
CO
CO
TD \/
C o
3
o
II
O
cx /\
E
o
o
c
bO
X
o
x:
o
c
CO
bO
S-
o
o
11
rH CO
03 i-H o
S- 3 II
CD S 2
c t. C\) 1 OJ
CD O o o 2 Cd
2 2 1
1 1
CO
CO n)
o C
c 3
3 CO O
O CD CX
CO Q, c E
CD E •f-l O
c CO O E o
.— CD O rt o
E -U CO CO
E 0) 03 O o o
03 S-
4J 4-> -p
•H •rH •H
2 2 2 2 2
133
1 o
o 1
o 1
CO
CO
4-5
o
- £o
2 1
e 4J>
O CD
O -P
CO
LTi
OO
1
•a
c
X O
1 O
o
1
o
CD
'^
O O
CO
O OO
O
CO
O
CO
LH
CO
2_
LPi -P
o 1 <— CO LO ro CD
o o ^ ^
CO i^ [^- ^- t^-
zs CO X3
c o T T T V 3
o
1
•rH O O LTiLO LTi O

c o
II O
1
1
O C\JO
CO CO
O CO
OO t--
^ -o
o /\
o
CO o
a c c
c o •rH
=!
O
D.
CD
t, ^ CO CO
CO
s
o
-P
CO
o
o CM to ---
on o i:
c 1 1 S- o
o o -Q o
1 o
f>o CO
o1
X OO CO cr:
o
CO CO
c
CO
o
o o
o (D
i-
3
> ^^
3
> '^ o —O "" ^
J-)
CO 1 o
^ > o > CO O
1
^ ^
O OJ C\J --^ 1
^
CO
^
CO
o OO o OO o o o
O O o O
1
LPl
o
1 1
o
1 1
O
1 o
CT^ ^ o
0^
o
^
cv
CO I>-
1 OO ( OO ( T 1
o
>, rH rH O rH .^ C\J
N :^ >> >> -rH >, O T
r— 1 CO C: rH t, O JJ O -rH O 1 M
CO i— 1 CO CO CO CO CO -i-> 1 O >,
^
rH
O II II II
iH II CO o >>
O :^0
1
^ i
C i-
(D O
o
1
1
(NJ
oc
^
fsl
cc
N Q,
a: -^
. rH
(M
cc
-
E
o
i.
o
1
1
— :
'-I
CO
II
t.
CO
11
- - - ^ -
a: CE cc
-
en
CO
^^ cc ^CO cc
•>
CO CO
aliphatic
aromatic
aliphatic
aromatic
•o O rH rH
acyl, •rH •rH -O >, >,
>> acyl,
o O -* J^ i,
CO CO S- rH CO
>1 >1 -O CO
s X X >,
CO
Peroxides
o ox:
^.. ^
(ii):
(iii):
(iv):
^ C .rH
(i): (D CD CO .rH -rH
CI. a. ^^ -^
134
1
Phos- Phos- Phos- Phos- Phos- Phos-
Compounds. Compounds. Compounds. Compounds. Compounds. Compounds.
CO
CD .
O Organic Organic Organic Organic Organic Organic
2
phorus phorus phorus phorus phorus phorus
See See See See See See
a
c -650(m)(out-of-
CD
(in-
CD Di: )
3 1 e
C o an
•i-i 1
plane) 1
4-3
c
broad)
p
o
o
CO
a x:
c o samples)
3 or
O <D sharp)
broad)
CX C-
E 4J solution)
o CO ~3100(m,
o ~36lO(m,
CHCI3 neat
c 1
CD
bO
o
1
(in CCli4 (in
>^
X
o
c
CO x:
bO o
-p
O CD
4->
CO E
o en
1
CM
T
X
iH CO II
II X CM
CO — CU
11
Oh
i- 3 >! CY-l a. II
E 11 Cu
C s- CO :i 1
CD O 1 II CU Cu
O [^ CC
CC
CC
a:
CO CO
CD
•0
T3 •r-H CO
•rH CD
CO X CO CO J-i
CD CD CO
CO 4-> JJ CO x:
CD CO CD CO 3 CX
>> c C C CO
r-l CO CO •H
•i-i rH x; x: x; x: x;
CX CX CX CX CX
CO CO CO CO CO
CD
x: x: x: x: £1 JC >,
CU Cu CU CU Cu
135
i1 —^ V^V 1i 1 . 1 1 i <
on en
o en cn en en -c tn
c •o c T!^ 7^ ^ o
3 c c C c 3
O 3 ^ 3 3 ^,
3
c:^ O o O Q Ci. O
C^ a. c
c
c •",
c Ci.
O B £= £= C s
o o o b o CJ o
c
o o o o
c
o i- i- t. J_^ 0)
o 3 3 3 3 tc b
•rH ^ c^ Cu-
—
5,-,
—c
4-.
^H ^H ,
— ,
r-J ,
C-H
o: •rH 3 3 3 3 "-^
c 3
CD 00 OO CO CO CO 00
-P
O o o O O O o o
2 'r-\ • ^ ..-* •^ •^ •l-f ^
C c c c c c c
CO CO CO CO CO CO CO
M to tiO bC bO bO bO
i- t. I. !L s_ t- t.
o o o C o O o
<D a; o (D (D o; o
0) GJ <D CD CD 0) 0)
w 00 OO OO 00 00 00
^
o
Jj y— ^—
o 0)
v-^-
CO CO
>.»-.'
0) i-
Jj o o
c
•-(
en o o
\0
\y , ^
—
c o ( 1
o II
o o
^
«
•o
c
o
D.
e
o
o
c
0)
hO
>> x:
X a
c ^ • s ,- —
en CO
^ N_^ x«_-^
jj uo LO
c m 1^-
bO o
II T 1
o o
/N
r— 1 nj
CO >— o
t. 3 J^
(D e ^
li^^^ ,<'^N
C L f T
0) O
O Cx.
O^
o c
cn
c;
en •o GO cn en
>> o .w
c
CD (D a)
o
r— en i 1 c en J-) en r-J TD
rH CD C^J ,zr C 3 CD CO CO o >, —I rH
E C ». • O O J-> C c c C !- X
nj o :,
^ — O Q. CO O o O o c o
JLj c •rH £ C^ C-H Ctj Cu^ Cw — c^
— —
1
• ,-H ^ S ^— -H O ^H .— 1
I— ^ SI
3 CO iD —1 o 3 3 3 3 3 O 3
cy CO CO CO CO CO CO CO
136
1 o )
in in
stretch samples stretch samples
bonding; bonding;
arise arise
CO
N-H N-H
4-> solid solid
o
2 of
hydrogen
values
samples.
of
hydrogen
values
samples.
in in
to to
Lowering Lowering
occurs hiêr dilute occurs higher dilute
due due
of
(stretch)
higher
groups
solution)
state)
with
solid state)
nitrogen
solution)
interaction (C-N)
solid
CO
obtained
(1700-I670)(s, (1680-I630)(s, (1680-I630)(s);
broad) attracting the

x: and
4J
CO
O (I650)(s, (I690)(s,
to to
•o (~1250)(m, are
c
3 due
(bend)
O
Q,
E electron attached
O values
o >C=0 >C=0
band
N-H >C=0
c
bO
O
t.
4-> broad)
broad)
1655-I620(m)(bend)
3520(m)(stretch) 3400(m)(stretch) 3500(w)(stretch) 3400(w)(stretch)
3500-3400(w) 1570-1515(w)
860-666(m,
X 860-666(m, 909-666(m)
c
2
1
CO (scissoring)
bO (stretch) l650-1580(m)
(wagging) (wagging) (wagging)

S-
O (bend)
1
(stretch)
1250-1020(m)
aromatic
I400(s)(stretch) l400(s)(stretch)
2
non-
O
1
conjugated 1342-1266(3)
(s)
amines)
amines
(for (for
400
iH CO CM cc N
CO 1— x X cc <"
J_3 2 2 2 CC
X
CM
E
C i-
O
O C)
1
1
O XJ
1
1
o — 1
1
2
1
cc cc cc CC
Secondary
Tertiary
E Primary Primary
CO
Amides Amines
137
) ) )
CO
CD
O
2
T3 CO
 (0
E CD
c D.
CD C
faO (D 3350-3310(w) CO E til E E
O >
CO x: o o
O O
in ^3-
o
909-666(m)
CO >-
2 (scissoring) CO CM CD LTi ITi
CM CM -H '— '—
1515(vw)
(stretch)
(wagging)
1 1 i- 1 1
O O CD O O
O O CO O LH
o
m 00CM -^ vo in
r- ^
to
hO
1250-1020(m) 13^2-1266(s) 1250-1020(m) 1342-1266(s)
aromatic aromatic
2 ugated
non-
O
1 non-
conjugated
amines
amines) amines amines

(for (for (for (for
conj
rH CO
CO .—1 CM CM
S- 3 CC cc 1
CD E X
2 Z
1
'^
Xm
C i- CC
CD O 1 tc
2
1
+
CC DC DC
salts
>>
r-H (continued)
Secondary
•rH Tertiary
E Primary
CO
Amines
Amine
138
' ^ ' ^ — ' ^ • .
CO
o
o
O
0^ '--
o
T3 CO oo
0) LT, 5 t—
C
4-)
o O O
O LH
c
O^
VD
in
t^
o T T T
o
1 3:
CO o o
c o
1
=O o
1
o
o
Ci CO
E CO ^^
O (D ^ o
CJ) £1 tfl c
S 0) o
c D. Jj '-^
CD C ,_^ ^^ ^^ ^_^ •« •*
1- o ^—
bO CD B E c
O > -—
CO
»—
ChH
C) —
^ —
-
CO
—
CO
—
CO dJ
> o
CO
^_^
i_ CO o o o o o o o —
£> IPI
4-> I
o u^ CO ^£3 LO o
^ o caD
^
c^ (M CD /—> LO CM ^-^ o •^ ^^ ^^
C\J C\J 3 CM CM -D CM a s
^^
,— a
1 1 1 1 CO CO c
o o
1 1
o O O O o o
1
0) O C^ o 0)
o o Cfi o CM O O i. Cvj L , in X3
—
c o
m t^
CM
^^ o .— >-D t^
CM
^
PO
J3 CO £) VD LO
t— >—
cd C\J CvJ
bO
s-
O
o
I
x;
o o o
o
o o
o
o
o
X 1 CO I on 1
X X X
CM
X
2 +
n::
2 +
1
X
2
d:
CJ o o
O tj CvJ
cc
on
CC
^ 1
+
1
+
1
>.
CO TD i. CO
>, CO o
CO i- C •.H ^-N
>, CO C -a cO L o CO
CO -^ c -H (D CO â.
-p o 4-> jJ
E c o i- CO o ,-H
CO c O CD D c CO
—Io 00 H C? tH v_^
E
<
139
1
x:
o
4-3 CO
CO
O
1
o
2 CNJ
/\
T
o
2
2
x:
o x:
^ o
CO S_ CD
o -!-> t.
o CO 4->
3 CO
c
O
CO ^
c CO CO
o
o CO CO
CO O LO
o ^ C7^
c ^ <\J
^
3 CvJ
o
CI
e
o
o
c
a>
bO 'co "e"
o
X O CTN
4->
2
1 ^ O
O ^ '--t~-
ro CO
1 ---1
O O CJ^
O O
on o ^
C\J
c
CO
bO
m T— c\j
i-
O p-
IR in
peak
in down
donating
in
spectrum
2
1
cm~*
11 allowed
2
(1576)(w);
unsymmetrical
lowered
1 1429 substituted azobenzenes
forbidden
electron
Raman
but
is to
r— CO
CO
i. 3
1
--H
2
/ ^C t
CD E CO 2
2
11
C ^ + 1- 11
2
O
X
2
2
1 V
cc
^ 1
CO
a
c CO
3 -o
E O C
r— 3 a. 3
•H •.-1 CO E O
e C CD O
CO o c o X E
IJL, E O o o o
E -H ISl tsl
<
lAO
{ — —
(P bO bO
c; c C
m :3 •rH •-H
jj •a c^ 1 C_
C CD CD
a o
1
<D i- X >
S a) •H CD •i-l CD
<D a sz CO S- Cm L
tH D 4-> CD
CD O o X3 ^-^ i3
Ci-l 11 s II fi
CD
>
ao O o CD CJ CD CO
ra /\ s /\ S CD
Q)
4->
•iH
4-5
S >^
4->
TD
•iH
III
o 05 C ) .-1 o C
2: bO COc o o Cti
<D CD c o C\l ^-~ o o >l
C £1 CD •H CM S t— c^ o
O jJ 4-> 4-> III t r o
£- d o. I 2 0> n CO
4-> O •.^ S- I o o
O -P
CD
o
CO
O
CO
^-' ,
f-
1>-
c— CD
1— 1 x: X5 cv CD
CD a -P CB C\J OO
CD S
D
C CO
•1-1
4-> x:
C o
o 4-)
o 0)
o
CO X3 CO
•o
c
3 CO 5
o
o O O
e o LTi O
o o CV-i O
o (\J CM
O
I
c OO o
CD
bO
c^
CM
O
^
^3-
O (M T—
4-5
•i-l
o
•iH a s o e •a
CD
505
c O 4-> O -p 4J •iH
CO
bO
^ OJ C\J OS 01 -P
CM x: CM o) bp 00 x: CM 0!
f- CM ex CM e 3 CM Ci CM S
O 1 —I I O -o •rH 1
O
1
O
vT)
rH
^r
r-\ t-
0)
o) 05
CM ^-- CM .:3- N ^ C^ '^-^
CM CM CM CM
iH 05
Oi iH o CO
L 3 X o
II
o
II
!=
C t-
2;
III
2
III
2 II
CJ
II
lu 1
2+
1
:0 2I I
2I
CE K
CO CO
CO
T3 CO 4J
m
CO CO r-{ CO c
O CO -rH 03
Ch 4-5 a s- .-H >,
>> E ^ 03 •rH P> •rH
O -H C C -1 i-
O S- c CO 03 03 C -P •rH
O -P
0 >> >. *t-i x:
C —1 N CO c 4J
OS C 05 •rH -H
CO CO ^-^ CO CO
O ca
141
1( —^ —
E
CO I 3
CD O
> o
<D CD 4->
CO CO Ci_i C ti-i
o CO bO O
4-> O 3 CO o
CO
1
to M
I
•'H Q.
0) E 3 o
+j o O
o o c J_
2 C —I bO ii
<D
3 V CD
cr o o O
CD II
t- a E C
< <i-i ^ CO •>-i
^bO bO bO
C C
o
CO
C -rH o
xs
o
•O CD
CD i- c o
•o
c
i. (D
JD
CO o
o CO i3 a.
n 1 o
1
CD
x:
•o iH
<D n o
3 D bO
C O CO CO <4-( c
•i-i •a •iH
jJ bO
C ,-. O O O O LO bO
o
o >H CM
o
IIo^ X
i^- CO
,
<o t— t— 3
,^ r- ,- ^ 2
II
o ,—
1
X
II
CO .*
^— y~^
c ^— 1
x: x:
3 o o o
o a 4-5 J->
ex
s -p
<D (D
J-
o
S- O 4J
o
CO
O
C7^
o CO JJ J-> <D LTi <\J
o 2
I
r— CO CO E ^ ^-N , ^^
D V ' v^-y' /\ E
O o o ô
1
c e >, f.
0)
o
D LTi o CO (M CO CM CO
bO
o
,
OJ
o
C\J
VO CO oo (0
s-
o
CD
.—1
D. -p
c
CO
•f-i
4J -O
o ty
E
S
I
bO rH C E
D O /\ >>
o E J=i CO
CO
1
1
r-\ m
o
I
Cfl r-H I
t. 3 O 2:
CD E II
o
II
C L
CD O
o
o
II
a
II
ci- o
-A . -/^ .
cc cc cE ce C\J
o
I
2_
O
1
fc,
cc
CO
c
>, rH c
r— e 1
rH CO •r-l
•r-i
CD ""* r-i E E
B c c E CO CO
CO CD CD CO jJ>
Dl. J-) 4-> U. O 4-)
CD CD CO
i^ i^ J
142
CO
-o
c
CO 3
CD o
-P
2O e
o
o
o
c
^
o
(P
00
S E O
>. >, jj ---
CO CO CD TD
CO CO S-, C
CO v-' --^ 4-> CD 1680-I650(vs)(trans)
CO JD
CD 1625-I6l0(vs)(cis)
CO CO
CD
3
o LTi LTi CO CO
v_- s_.
stretch stretch
850-750(vs)
CM
C
CO
o
<—
CM
»—
mo
en a^
II OO v£3
C O O O O
O
cl;
II
2 ^D
o^ri
2
o CY-)
1
1
t~-
m1
vO -N=0 >N-0
1<- ^ /\ CO tr-
CO
•o
c
3
o
s symmetric)
o
o >N-0
c
<X)
bO
(
O
S-
c (asymmetric)
bO >N-0
1-
o
2
1
>H CO
CO <H
s- 2 CM o
CD S O 2 II
c t. 2 III 2
CD O 1 O
a
1
t, O
DC
1 O
cc
>> CO CO
CD
4-5 compounds) +j
e CO
Nitriles
(cyano- •H
CO t. !L
-P -P
•rH H
2 2
143
CO
CD
4-i
O
2
(1520-1500)(s)(vapor)
e (1500-I480)(s)(neat)
CO
i_ o
CD
x:
4J )
CD
3
o •o
stretch
C c
CD N-N(1150-925)(m)
4-> JD
c
o O
o 2
CLJ
>N-0
CO
^^ CO
c CO '^ i. O
> CO Q) -H
O ^^ v^ 3 4J>
D. O O O CO
E rH x:
O
CJ >N-0
(stretch) c\j
en
^ m
.=r
T— 4J
(X
^
1 1 CO rH
C
CD
O
o>
'^
in X3
CO
bO on (>n j_ c
O ^ ^ O CO
S- CO x:
4-> ,^ .^ X3 4J
CO CO ^^ '-^ CO
> > CO CO CO
^^ v^ ^- v_, CO CD
O O CO O O -H
^3- c\j o o ^r '^
c on Ln on c 4J
stretch)
Lpi
,— -—-,— ^^-^ COCD
CO
bO -N=0
in
1 E
>5 o
1 Ê E
1 '^ E a
CO >> vo E o cr
1
t.
O ( ^C0<7^>>
vocoonco
J3-cnLn>>t-<D
LPicflmcocOS-
assign)
2 (difficult
O
1
870
to
r—
o II
2
ovj :^ >>
2
General Formula 1
O i-H L
2 CO CO
—
/\
(N
1 II II
CC CC cc CC cc
1—
Aliphatic
E Nitrocom-
pounds
Aromatic
samines
CO
Nitro-
144
1 — / ^ 1
^
1 y'-^ —
y
3 O O
Q) !-> CXD OO
1 r-i -1 tr- CO
O -O -P 1 )
m CO CO in o
O 4-> X3 C7^
J- CO 3 f- O
C\J
b ^ h
4^ C !L CO --^ •-' . Cw Ci-i cu,
-H
c
D O
O C
.. O 1— M rH
CD C CM 3 3 3
CD 0) •rH .. O O t- CO 00 00
-U 1 L bD 4J C --H -rH
O CO C CO t, -p -P - o . o . o •
2 O CO •^ CD 3 .— 3 --v •rH CO •rH CO •rH CO
o CO L • S_ ^ 4-> in ^ O c -cj c -o c -a
CM -O iU CD 4-> -rH .rr •-H t-- CO C COC CO c
C CO N 4_) CO -P t— -P C-- bO 3 hO3 bO 3
a 3 cy -^ O Q. CO 1 CO 1 t. O L O J- o
C O S- s. CO X3 LTi £> O O c:x o cx O Q.
CO Q. CD
E -o e
S^
CO
C 3
O CO
LTi
t-
3
CO
^
CO CD
s
O CD
E
O CD
E
O
o o C -H
^ O CO -c? x: .^ 1
v_^ 1 ~-^ 0) o O O CD O
O -P £3 cQ 00 00 CO
1 1
-1 o CD LPi
rH C
CO
t.
CO ^ '-- o ^
^
c^n
» « ^CO (U
c
-P
i, x: -
o o
m
--^
O
CO CD O O
CO
L
cv^
^-^
-H >
O
4J O
CD
sz x:
• —s
CO
-
,^^
CO
CV-i
O
CY-)
Ci.
1
Ci_,
'-
CO
^
'-~>
CD
t,
-P
LPi
t-
•o -p O -— ^-^ - O --^ O CO O
Q>
3
o
C stret (3075 (out-
•rH 1-U95 ring
1585-1539 phatic) (920-720) (2000-165 (1600,157
C -- matic)
O
O I
N=0
151
N-H C-H C=C
CO
o
c
o
o •fH
o. i-
E
o
o1
-^
d)
o 2 S
s
c >,
<D
bO
O
^
CO
^^
o
-rH
t.
JJ
c o1
<1>
s
bO 2 S
>.
O CO
^
CO
2
O
1
r-H CO
^ en
CE CM
n3 r-H /
/
X
2
1
i- 3
V
2 2
CD E o /rt^ CM III
C !- II
< { ) 2:
11
"^v O o
<D O 2 \v J -/ \ 00 CO
O Cl, 1
v-^/ CC
1 1
CC CC CC
CO
-o CO 1
>, 1c CD 1 1 c
1— O 3 C •rH CO CO
•iH CO O •^ CO C CO >,
E O Q. a ^
.-H
d) O (D O CO
CO i. E •rH Q-, C c^-, -a O CD
t, J^ O L rH -r^ rH •r-l •rH 4J
•^ O >, 3 E 3 E x: CO
2 a. OO 00 H
145
cm"'
frequency
region; 50-150 hydrogen-bonding.
CO
c
CD
s of
s popular
o that
o
to
lowering
around
Only due
3 CO
5
o o
CO o o
LTi O
CD C\J O
<o T
x: 1
§ o 1 LO
o o o
\/
C\J
o <o
CO OO X 1 o
a 1 00 II
o
1 1
c e 00 00 1
3 o 1 1 cc
O
cx c
s •rH CO CO
o
o 1 CO LTl
CO o
II o CJ^
3 CD 00 o 1 1
Q-i JD
E
CO I>- o
CO
1— CO
3 3 CT> 0^
00 2
CD CO CO
> o
C CO .H in LTl
CO J, CO ro
bO O -JJ
CD
S-
o
II
cy^ e 1 1
/N e o o
>, o
OO C\J
o CO CO CO
•r-i
J- o O O
O
-P
CD
OO
OO
o m
CM o
II B
00 S 1 1 1
CO
in O
CO
ITi
C7^
< ^3- C\J O
cNj
CC
O cc
O
CM
iH CO cc II 1
CO 1— 1
fsl
cc cc 00
t, 3 00 00 cc 1 1
2
1 1
CD e 1 X CM 1 2
c t- 00 1 00 II II II If
CD O 1 00 o 1 00 00 00
CM
00
CM
1 q:: C\J CM
cc cc en cc CC
r-H
c
1— o
CO >1 Q-.
CD >. rH
CO CO c o rH 3
>> CD c CO CO CO
.-H CO CO CO B
2 2
1 1 1
• -—
-p CD CD •iH
Q. jj a ^H
CO rH CO CO •f-t •nH
3 o Ci-i <^ Ct-( •H •rH
CO r-l r— rH •rH
•rH 3 3 3 •rH
Q 00 OO 00
146
) 1
groups
cause reduces acids
by absorp-
absorption
spectra
CO group
p numbers
bands
c donating
bonding
sulfonic
cm~^
E frequency
E
O phase aryl
o wave
cm"^
frequency
broad
the Hydrogen
Hydrated
1230-1150
Electron
slightly.
10-20 higher
Solid lower
tion. show
the
on
CO CO
o t-
fV-1 CO
en m^
c\J
^^
1
O O
1
LPi
CO a^ O vO
en en CM
en en en
-p
o O O
r- CM
(Continued)
X1
X1
cm~^
(
in
Compounds
II
00
Numbers
CO CO CO to CO
CO
Sulfur Wave
LTi o
CM
o
in LPi
LTl
(Symmetric)
T T o T
>S=0 T 1
o C3^
o .
o
rganic
to CM
o
o
co CO to CO CO
CO
LTi LTl o CM o
CV-)
OO
CV-I
en
o on
LTl CO
OO
(Asymmetric)
,_ ,
>S=0 T 1
o
1 1 1
O
t>-
CM o
LTl
o
in
en en ro OO CO
O
rH
to rH
CO
X
CM o en
,—
L 3 CM
1 1
CM X 1 oCM
E CM O O OO
O
OO
O
c u O 00 00 O
o 00 1 1 00 00 00
1 1 1 1
CC CC cc cc
CO
CO acids
o
-a CO to CO
r-i
E p CO o
•-{
.-H-a
>, •M
CO to (anhydrous)
E c c C CO C L
to o o o O -P o o
C<-H Cl-H Cm Sulfonic
Cm i-H Cm rH
rH .H rH rH to r-l £1
3 3 3 3 CO 3 O
00 OO 00 00 00
147
than
effect
reduces
effect
absorption
larger
>S-K)
CO electrone-
pi CO
c bonding
substituents
Inductive c
CD CO
(+)mesomeric
is
E the P>
E cx
o CO
o frequency
o
s_
sulfur (-)
Hydrogen increase frequency
slightly; gative
the The its

of
CO
aryl
thioester)
(S-alkyl
CO CO
(S-aryl
S
for
o o (2175-2l40)(s);
o
CO c^
o
CM
O
o
LH
CD CM
T
(1710)(s)
values
x: 1 1
o
4-) o O O
T3
o
LO
CM
(I690)(s) o
<X>
3 thiocyanates
CM
C
•.-I
4-> of OO
higher
X
c II -C=N
Q 1
o 00 o -C- OO
o 1
CO
o
c 1
3
o
a 00
II
E
O
o
3
Cw
I—
3
CO
(Symmetric)
>s=o
c
CO
bO
(Asymmetric)
>S=0
.-1
X CM
CO
CO iH eg 2 CC
t-3 III 00
X
E
C !U
o
?
00
o
1
— ôo
CJ)
00
1 o
1
1
— ô X
00
OO
1
O
1
IJ-i CM
<
1 1
CC CC cc cc
CO CO
into
i- CO
CO sul- p>
CO 4-> o
--I •o tri- c CO c
•rH •rH CO
E X Thiocarbonyls
>, CO x:
CO o merized
cyclic
o I-H rH cx
Q-H (not fides) o o
iH r-{ •rH •2 .2
3 x: x: x: x:
00 E-
1A8
— — . 1 — 1 — '
a -p S
o o
^m S
t.
tfl
-a o
v^ -rH c C\l
O
CO
*<-!
C
CO
X3
CO
1
vo o o
on
1
o
v-'
>, r-
xn CO
x: o .'-^
o CO 4-> o •rH ^-v y~^

o
1
o +j
CD
o
1
CD
t— ^
C/J
1
CO
^^
CO
v_^
o
1
o o
•r--\ i- 1 £) 1 (Y-) CM
00 43 o 3 1 LPi CM
O
CO
/\ m o> O t
»— w
O •rH o
o -a
« ^— I /
bO bO faO fciO bO
C C c c c
iH rH •rH H •rH
^ ^ ^ ^ JiC
o o o o o
o o o o o
5:: -O £- i^ L S- i-
C
O
1
CD
/\ X3 CO CO CO CO CO
o o
>^
o
VD
O
VO
O
MD
>X)
CM CM CM CM C\J
CO
o
c
o
D.
e V o
o CO o O ^—^ ^— o o
o t-
<D
00 CD
i^
C3^ O
CO
CO CO cr> CT\
c OI
-P 1 O LH 1 1
^
1
o
o
S O
C3>
o
CM CO t-
LO o
C3^
o
CJv
C CO CO 1 1 CO CO
CD
>
00
CO
bO
o o o
OO OO CO
O 1
00 o
C7>
o
C3>
o
CT^
CO CO OO
sz o o
o o ^^ LO
X -p ,_ CO ,—
1 CD CM
•rH t. 1 in 1
00 4J o
OO
en
,
O
VO
, CvJ CO
CM ) CvJ
,— 1 CO
CO i-H a: 00 a::
S- 3 >> cv^ CM o I o
(D e tn nc X an ^^—^
o
C i- •rH ,H r-t •rH l-^ r-\ 1
CD O 00 CO OO CO 00 OO •H CO
O tj
CE
X
cc
I C^
cr:
PO
cE
^
cc
-x
cc
00
a:
X
rH
>^
^ tn
^ iH >. 1—
iH >i ^ CO >> CO CO o t. o s
>. CO ^ l-l CO X CD
1
r-{ CD •rH CD •rH CO 1 CO

O
ô C 6
.-H (0 tH CO t- C. •rH r-\ rH i. >-, CD
•rH Q) C CO •rH •p CO CO CO O -rH O -P X C
id c o •rH tn CD r-^ X •rH X >. s^ >> CD O CO
CO CO s Q H H < o -o O O .P O -P
Ix^ M •O •H
>» CO
CO o 00
149
11 )' 1 ) . ) 1- o o
up
stretch
in
CO
cm"
4-) shift
o to
65
2 solvent
change
>P=0 due
to
can
stretch
-OH
0} '—- r— ^-~- 1— '—^ r-H

T3 ^ >! r-H >> i-l >^
C >. ;- >. s.
3 .^ 03 :^ 03 .ii: 03
O r-{ ^— .H ^-'
CI. 0) '-^ 03 '-- OJ
'-^
E >p-o-c<
--^ CO -~^ CO •-' CO
O stretch
o CO
^^ t—
LO CO m COin
-^ c—
CO
3
o CO
LA 1
O
LTi
CO
I
o
m
oo
o o
1
O O o o
o ^ en C7^
-- m ^ in
x: 1 1 CJ> C7^
a
1
CO
o
x: ^ 'e
o o O
CO CO CM
'e 'e 'S. CM CM
c >P-H stretch CM CM CM
CO o o
— m
O
1
O
1 1
bO
J-
CO x:
on c^ CO
O
in
O CM CM --- m
CM
ro
CM CM
1300-1100(s) 1285-1260(s) 1315-1290(s) CO CO (0 CO
o
o
CO
O LTi o
en
in <T>
O 4J »- o CM
II o
(doublet (doublet (doublet 1 1 1 1
c LO, LO in
'
CO CM
CM
CO ^ CM
1— 1 03
03 >— CM
tr
^ i O o o
c ^
O a,
11
1
a.^ — a;
C- — cT Ô
o
1 1
CO CO
J-> Jj
03 03
c c
1— o
x:
E Phosphates
alkyl
aryl D. Phosphine
alkyl
aryl §.
oxides
o; CO CO
O o
x: x:
a) b) a) b)
150
1 ) o O
o
CO
4->
o
2
x:
o
4-3
o t-
2700-2200(3, broad)(assoc.
CO
0)
c
4-)
c
o
o
x:
CO
o1
o
4->
a o 
CO
C
CO
bO
o CO
> CO 1310-1200(s)
band)
x: o o
O
o
4J
C30 o
CM
0)
T T
11
/^ 4J.
CO
o LO (single
CM C\J
CC
r-H (13 X CM
o
CO
i.
0)
3
E
.-H
o
CC
o, —
CC
o.
1
—
C t- II CM o
0)
O
O
Cx. a- cc O
CC
a.
CM
1
—
cc o::
CO CO
3 3 1
>> S. CO
— O O CO o en
•rH x: CO x: Qj x: o
s D. -a ex 4->
CO CO •'H CO -rH O CO
o o o s s- x:
x: to SZ CO >-> ex
Cu
151
I 1 — —V^ 1
x:
o O
-IJ O
CD ,
J_ <—
4-> 1
CO O
CNJ
o
1
II
• —
y
E •
>i E
o CO >>
+j CO CO
en v_y V_'
s- o o
-p O CO
CO CM O
rv-) T T
X O O
(J) cn o
1
CO • y—
E • ^^
c x: >, E
3 o CO 5^ g
O ^~. >i
Q. ^
-i-j
^—^
CO
— CO
CO '-^
E i. o o CO •
O CO
1
O E jj --- s
O o CO CM O
C7^ CO
c CM
X
1 1
(D CO o o o
o
1
bO S- Ln O LTi CNJ
O
-— £1
CD /^ on
r —
CM
T
^
CO
kO
1
CO E
X D
C
>
c cfl
CO IS
bO
J-
O x:
o
4-J o O 0)
0) ,— c CO
i_ o o^ o o o
4J t
O r- ^ C7^ o
CO 1 in i- CM CM
o O
1
CD
X o ^
1 1 1
CM > f- o
t ro
CO ^
LPi O ^£) o
o
1
T ^- vX> in
/^
i-H CC r-^ S,
CO .-1 t, o CQ 1—
L a
E II 11 II 11
C J-
<D O X X X X
O tL,
CO CO
>> CP <u CO
r—
l-i
•a
•r-l
a
••-I
CD
a
CO
cu
E e S- •iH •a
CT3 o o s •rH
[x. 3 •-t o •a
.—1 x: t. o
tL, o CQ (—
152
V. Tables for Nuclear Magnetic
Resonance Spectroscopy
155
Tables for Nuclear Magnetic Resonance Spectroscopy
The following tables provide valuable information on NMR spectroscopy. These
tables are by no means meant to cover the whole field of nuclear magnetic
resonance but should be more than adequate for the routine determination of
organic compound identity or structure [1,8].
REFERENCES :
[1] Silverstein, R.M., Bassler, G.C., Morrill, T.C., Spectrometric

Identification of Organic Chemistry 4th edition, John Wiley, New York,
,
1981 .
[2] Williams, D.H., Fleming, I., Spectroscopy Methods in Organic Chemistry ,
3rd edition, McGraw-Hill, London, 1980.
[3] Lambert, J.B., Shurvell, H.F., Verbit, L. Cooks, R.G., Stout, G.H.,
,
Organic Structural Analysis MacMillan Pub. Co., New York, 1975.

,
[M] Abraham, R.J., Loftus, P., Proton and Carbon-1 3 NMR Spectroscopy , Heyden,
London, 1980.
[5] Bruno, T.J., Tables for Instrumental Methods of Chemical Analysis Center ,
for Chemical Engineering, Chemical Engineering Science Division, Boulder,

1985.
[6] Jackman, L.M., Sternell, S., Applications of NMR Spectroscopy in Organic

Chemistry 2nd edition, Pergamon Press, New York, 1969.
,
[7] Varian Associates, High Resolution NMR Spectra Catalogue , Vol. 1, 1962;
Vol. 2, 1963.
[8] Bovey, F.A., NMR Spectrometry , Academic Press, New York, 1969.
[9] Tsujihara, R., Furukawa, N. , Oae , S., Bull, of Chem. Soc . Japan, 43,
2153, 1970.
157
Magnetic Properties of Some Nuclei [1,2]
Element Isotope Abundance Spin Number Resonance Frequency

(?) (magnetic at 4.2276 Wb/m^
moment) (Hz)
Hydrogen ^H 99.984 1/2 180.0

^H 0.016 1 27.6
192.0
^H <10"' 1 /2 19.34
Boron log 18.83 3 57.75

81 .17 3/2
Carbon 98.9
i^C 1 .1 1/2 45.3
Nitrogen 99.64 1 13.0

15^ 0.36 1/2 18.24
Oxygen 16Q 99.76

^'0 0.04 5/2 24.40
Fluorine 19p 100 1/2 169.34
Silicon 2«Si 92.28

^^Si 4.70 1/2 35.76
^°Si 3.02
Phosphorus 31p 100 1 /2 72.87
Sulfur 95.06
0.74 3/2 13.81
4.2
Chlorine ^=C1 75.4 3/2 17.64

^'Cl 24.6 3/2 14.68
Bromine ^^Br 50.57 3/2 45.1

8lBr 49.43 3/2 48.6
Iodine 1271 100 5/2 36.0
REFERENCES :
[1.] Silverstein, R.M., Bassler, G.C., Morrill, T.C., Spectrometric

Identification of Organic Compounds 4th edition John Wiley, New York,
,
1981 .
[1 . ] Streitwiesser A, Heathcock, C.H.,

, Introduction to Organic Chemistry ,
MacMillan, New York, 1985.
158
E
Q.
sz
4-i
•o
c
> I I 1 1 1 I I ^ I 5
8 IllB^ld 5 i i
0)
159
Proton NMR Absorptions of Major Chemical Families
The following tables give the region of the expected nuclear magnetic
resonance absorbtions of major chemical families. These absorptions are
reported in the dimensionless units of parts per million (ppra) versus the
standard compound tetramethylsllane (TMS):
CH3
CH 3""S i""CH 3
CH3
The use of this unit of measure makes the chemical shifts independent of the
applied magnetic field strength or the radio frequency. For most proton NMR
spectra, the protons in TMS are more shielded than almost all other protons.
The chemical shift in this dimensionless unit system is then defined by:
^ ^ ^^f ^ X 10^ (V -1)
where Vg and v^ are the absorption frequencies of the sample proton and the
reference (TMS) protons (twelve, magnetically equivalent), respectively. In
these tables, the proton(s) in question are indicated by underscore. For more
detail concerning these conventions, the reader is refered to the general
references listed in the introduction of the tables for NMR.
160
Hydrocarbons
Family 6 of protons underlined
Alkanes CH3-R -0.8 ppm
-CH^-R -1 . 1 ppm
-CH-R -1 . 4 ppm
(cyclopropane -0.2 ppm)
Alkenes CH3 CH3-C

>C= C< -1.6 ppm >C=C< -1.0 ppm
-CH2 -CH2-C
>C= C< -2.1 ppm >C=C< -1 .4 ppm
-CH -CH-C
>C= C< -2.5 ppm >C=C< -1 .8 ppm
>C=C< M 4.2-6.2 ppm
Alkynes CH 3""C— 1.^ - -1.7 ppm CH3-C-C=C- -1.2 ppm
-CH^-C=C - -2.2 ppm -CH^-C-C=C- -1.5 ppm
-CH-C=C- -2.7 ppm -CH-C-C=C- -1.8 ppm
R-C=C-H -2.4 ppm
Aromatics G
Range: 8.5 -6.9 ppm
P-
G=Elect ron withdrawing G=Electron donating

(e.g. -C-, -NO2, -C=N)
, (g., -NH2, -OH, -OR, -R)
o-p-closer to 7.3 Ppm
(more upfield)
o,p-c loser to 8.5 ppm
(more downf ield)
161
Organic Oxygen Compounds
6 of protons underlined
Alcohols
CH3-OH 3.2 ppm RCH^-OH 3.4 ppm R^CH-OH 3.6 ppm
i I I
CH3-C-OH 1.2 ppm RCH,-C-OH 1.5 ppm R2CH-C-OH 1.8 ppm
R- Q-H (1-5 - depending on concentration)
Aldehydes
CH3-C-H
GO
II
CH3-C-C-H
I II
2.2 ppm
1.1 ppm
RCH,-C-H
II
RCH2-C-C-H
I II
2.^ ppm
1.6 ppm
R2CH-C-H
~ II
2.5 ppm
Amides
See Organic Nitrogen Compounds
Anhydrides
~ 00
CH3-C-O-
II
CH3-C-C-O-
I II
1.8 ppm
1.2 ppm
RCH,-C-0-
II
RCH2-C-C-O-
I II
2.1 ppm
1.8 ppm
R2CH-C-O-
~
~l
II
R2CH-C-C-O-
II
2.3 Ppm
2.0 ppm
/C. /C,
C yc 1 i c CH^ \ CH-^ \
/°
3.0 ppm
CH2
/ 7.1 ppm
CH^ .
^C
1
162
Organic Oxygen Compounds (cont.)
Carboxylic acids
CH3-C-OH 2.1 ppm RCH,-C-OH 2.3 ppm R2CH-C-OH 2.5 ppm

""11
II ~ll
CH3-C-C-OH 1.1 ppm RCH2-C-C-OH 1.6 ppm R2CH-C-OH 2.0 ppm

"~l II ~"l II
R-C-O-H 11-12 ppm

II
~
Cyclic Ethers 1 . 9 ppm

2.7 ppm
2.5 ppm [^^^0
i1.7 ppm
\ y 3.8 ppm
6 ppm .7 ppm
/\
1 . 1
^^ -^ 1 . 6 ppm 3.6 ppm
V,
3.8 ppm\ y M.7 ppm
\q^ 3.6 ppm
1 . 9 ppm
4.5 ppm
6.3 ppm
7.4 ppm / h.2 ppm
Epoxides
See Cyclic Ethers
163
Esters
CH3-C-OR RCHj-C-OR R2CH-C-OR
R = alkyl 1 . 9 ppm 2.1 ppm 2.3 ppm

R = aryl 2.0 ppm 2.2 ppm 2.4 ppm
CH3-C-C-OR 1.1 ppm RCH2-C-C-OR 1.7 ppm R2CH-C-C-OR 1 .9 ppm
CH3-O-C-R 3.6 ppm RCH2-0-C-R 4.1 ppm R2CH-O-C-R 4.8 ppm

~~ ~" II
II
CH3-C-0-C-R 1.3 ppm RCH2-C-O-C-R 1.6 ppm R2CH-C-0-C-R 1.8 ppm
Cyclic 1.5 ppm
2.1 ppm 4.4 ppm 1.6 ppm// \ 4.1 ppm
2.3 PpmX ^0 2.3 ppm
Ethers
CH3-O-R RCH2-O-R R2CH-O-R
R = alkyl 3.2 ppm 3.4 ppm 3.6 ppm

R = aryl 3. 9 ppm 4.1 ppm 4.5 ppm
CH3-C-O-R RCH2-C-O-R R2CH-C-O-R
R = alkyl 1 . 2 ppm 1 . 5 ppm 1 . 8 ppm

R = aryl 1 . 3 ppm 1 . 6 ppm 2.0 ppm
164
)
Isocyanates
See Nitrogen Compounds
Ketones
CH3-C- RCH^-C- R2CH-C-

CH3-C-C- RCH,-C-C- R2CH-C-C-

I II I II "ill

a - hydrogens 2.0-2.3 Ppm (n>2)

3.0 ppm (n=2)
1.7 ppm (n=1
hydrogens 1.9-1.5 ppm
Lactones
See Esters, cyclic
Nitrocompounds
See Organic Nitrogen Compounds
Phenols
Ar-O-H 9-10 ppm Ar = aryl
165
Organic Nitrogen Compounds
Amides
of proton(s)
6 Primary Secondary Tertiary
(underlined) R-C(=0)NH2 6,ppm R-C( = 0)NHRi 6,pprr R-C(=0)NR,R2 6,ppm
(i) N-substitution
-C-N-H 5-12 5-12 — w>
a) alpha
-C-N-CH3 -2.9 -2.9
-C-N-CHg- -3.4 -3.4
1)
-C-N-CH- -3.8 -3.8
b) beta
-C-N-C-CH3 -1 .1 -1 .1 ~1 .1
I '
-C-N-C-CH^- -1 .5 -1.5 -1.5
-C-N-C-£H- -1.9 -1.9 -1.9
(ii) C-substitution
a) alpha
CHj-C- -1.9 -2.0 -2.1
"'CH2"'C~ -2.1 -2.1 -2.1
-CH-C- -2.2 -2.2 -2.2

""II
166
:
Amides (cont.
of proton(s)
(underlined) R-C(=0)NH, 6,ppm R-C( = 0)NHRi 6,ppn' R-C(=0)NR,R, 6 ppm
b)beta •
CHj-C-C- -1 .1 -1.1 -1.1
-CH,-C-C- -1.5 -1.5 -1.5
-CH-C-C- -1.8 -1.8 -1.8
Amines
of proton(s)
(underlined) R-NH2 6, ppm RN-HR 6, ppm RRRN 6, ppm
(i) alpha protons
>N-CH5 -2.5 2.3-3.0 -2.2
>N-CH^- -2.7 2.6-3.4 -2.4
>N-CH< -3.1 2.9-3.6 -2.8
(ii) beta protons
>N-C-CH, -1.1
>N-C-CHy- -1.4
1
>N-C-CH< -1.7
Cyanocompounds (Nitriles)
(i) Alpha hydrogens 6, ppm (ii ) Beta hydrog ens 6, ppm
CH,-C=N -2.1 CHj-C-C=N -1 .2
-CH,-C=N -2.5 -CH,-C-C=N -1.6

1
1
1
1
-CH-C=N -2.9 1
CH- C-C=N -2.0
167
Imides
i) Alpha hydrog ens 6, ppm (ii ) Beta hydrog ens 5, ppm
CH,-C-N-C- -2.0 CH3-C-C-N-C- -1.2
H H
-CH^-C-N-C- -2,1 -CH.-C-C-N-C- -1.3
OHO
I 1
H
1
-CH-C-N-C- -2.2 -CH-C-C-N-C- -1 .4

1
OHO
1
Isocyanates:
(i ) Alpha hydrogens 6, ppm
CH^-N=C=0 -3.0
-CH,-N=C=0 -3.3
-CH-N=C=0 -3.5
Isocyanides ( Isonitriles) ; Isonitriles: (See Isocyanides)
( i ) Alpha hydrogens 6, ppm Isoniocyanates 6, ppm
CH3-N=C; -2.9 CH3-N=C=S -3.4
-CH^-N=C; -3.3 -CH,-N=C=S -3.7
-CH- N=C: -4.9 -CH -N=C=S -4.0
Nitriles 6, ppm
-CH2-0-N=0 -4.
Nitrocompounds 6, ppm
CH3-NO2 - 4.1 -CH^-NO 2 - 4.2 -CH-NO2 - 4.4
CH,-C-N0. 'CH2 ~C-N0 2

- 2.1 -CH-C-NO, - 2.5
168
Organic Sulfur Compounds
Family 6 of proton(s) underlined
Disulfides CH3-S-S-R ~2.H ppm CH3-C-S-S-R ~1 .2 ppm
-CH2-S-S-R -2.7 ppm -CH,-C-S-S-R -1 .6 ppm
-CH-S-S-R -3.0 ppm -CH-C-S-S-R -2,0 ppm
Isothiocyanates CH^-N=C=S -2.4 ppm
-CH,-N=C=S -2.7 ppm
-CH-N=C=S -3.0 ppm
Mercaptans CH3-S-H -2.1 ppm CH3-C-S-H -1 .3 ppm

(Thiols)
-CHg-S-H -2.6 ppm -CH,-C-S-H -1 .6 ppm
-CH-S-H -3.1 ppm -CH-C-S-H -1 .7 ppm
Sulfates (CH3-0)2S(=0)2 -3.4 ppm
Sulfides CH3-S-R -2.1 ppm CH3-C-S-R -1 .2 ppm
-CH2-S-R -2.6 ppm -CH,-C-S-R -1 .6 ppm
-CH-S-R -3.1 ppm -CH-C-S-H -1 .9 ppm
169
Organic Sulfur Compounds (cont)
Family 5 of proton(s) underlined
Sulf ilimines CH^-S=N-R2 -2.5 ppm
R»
Sulfonamides CH3-SO2NH2 -3.0 ppm
Sulfonates CH3-SO2-OR -3.0 ppm
Sulfones CH5-SO2-R2 -2.6 ppm
Sulfonic acids CH5-SO3H -3.0 ppm
Sulfoxides CH5-S(=0)R -2.5 ppm
-CH7-S(=0)R -3.1 ppm
Thiocyanates CH^-S-C^N -2.7 ppm
-CH^-S-C=N -3.0 ppm
-CH-S-C^N -3.3 ppm
Thiols See Mercaptans
170
SOME USEFUL ^H COUPLING CONSTANTS (IN H^)
1 ) Freely Rotating Chains 2) Alcohols with No-Exchange

as in DMSO
H 1 ° - triplet)
I
5 .)- 2° = doublet) broad
>C— OH 3° = singlet)
Then add TFA, all = sharp single
~0
3) Alkenes
1
•H
H** ^H I
I
.-.. I
>c .c<
C C ^c = c^
// W
C C
k) Alkynes 5) Aldehydes
.
-2 1-2 2- 3
H-* te-H
/
>C — C=C-
^ ^'
I
C
W // w
c,
/
6) Aromatic
Adapted from the work of Professor C.F. Hammer, Georgetown University,

Washington D.C.
171
in Incompletelv Deuterated Solvents
Solvent Formula Group 5 (ppm)
d.-acetic acid CD, COD Methyl (CD 3-) 2.05
Hydroxyl (-0D) 10-12^
dg-acetone (CD,),C=0 Methyl (CD 3-) 2.05
dj-acetonitrile CD3CN Methyl (CD 3-) 1 .95-2.05
dg-benzene CsDe Methine (CD-) 7.2-7.3
d^-chlorof orm CDCl. Methine (CD-) 7.25
di 2-cyclohexane CeDi Methylene (CDj-) 1.M0
d^-dichloroethane CD2CICD2CI Methylene (CDj-) 3.69
d^-dimethyl- (CD3),NC-D Methyl (CD3-) 2.75

II
formamide (DMF)
Methyl (CD3-) 2.95
Formyl (D-C-) 8.05
dg-dimethyl- (003)280 Methyl (CD 3-) 2.5

sulfoxide (DMSO)
Absorbed water 3-41
dg-dioxane ^0
\ /
Methylene 3.55
dj g-hexamethyl- [(CD3)2N]3 P=0 Methyl (CD 3-) 2.60

phosphor amide
d^-methanol CD30D Methyl (CD 3-) 3.35
Hydroxyl (-0D) 3-6^
d2~methylene CD2C12 Methylene (CDj-) 5.35

chloride
dj-nitromethane CD3N02 Methyl (CH3) 4.33
172
in Incompletely Common Deuterated Solvents (cont.)
Solvent Formula Group 6 (ppm)
dg-pyridine -N, C-2 Methine 8.70
o C-3 Methine 7.20
C-4 Methine 7.58
d g-tetrahydrof uran a-Methylene 3.60
B-Methylene 0.75
dg-toluene CeDsCDs Methyl (CD3-) 2.3
Methine (CD- ) 7.2
dj-trifluoro- CF3COOD Hydroxyl (-0D) 10-12^

acetic acid
d2-water D2O Hydroxyl (-0D) -A

3.5-6 1
^ Exact value depends on the solute nature and concentration.
173
^^C Chemical Shifts of Useful NMR Solvents
Solvent Formula Chemical Shift (ppm)
acetone-dg (CD,)2C=0 29.2 (CD3) 204.1 (>C=0)
acetonitrile-dj CD3C=N 1.3 (CD3) 117.7 (C=N)
benzene-dg CeDe 128.4
carbon disulfide CS, 192.3
carbon tetrachloride CCl^ 96.0
chloroform-dj CDC13 76.9
cyclohexane-di2 CeDiz 27.5
dichloromethane-dj CD2CI: 53.6
dimethylformanide-d. (CD 3),,NCD 31 (CD3) 36 (CD3) 162.4 (DC=0)
dimethylsulfoxide-dg (003)2 s=o 39.6
dioxane-dg 67.4
"C>
methanol-d^, CD3OD 49.3
nitromethane-dj CD 3 -NO 2 57.3
pyridine-dg
9 124.0 136.0 150.0
1 ,1 ,2,2-tetrachloro- CDCI2-CDCI2 75.5

ethane-d2
tetrahydrof uran-dg
r—\^ 25.8 (
O'
trichlorofluoromethane CFCI3 117.6
Water (heavy) D2O -
174
VI. Tables for Mass
Spectrometry
177
Natural Abundance of Important
Isotopes
The following table lists the atomic masses and relative percent
concentrations of naturally occurring isotopes of importance in mass
spectroscopy [1-3].
REFERENCES :
[1 ] Rose, M.E., Johnstone, R.A.W., Mass Spectrometry for Chemists and

Biochemists , Cambridge University Press, Cambridge, 1982.
[2] Weast, R.C., ed.. Handbook of Chemistry and Physics, 63rd Ed. , The
Chemical Rubber Co., Boca Raton, 1984.
[3] McLafferty, F.W., Interpretation of Mass Spectra , University Science

Books, Mill Valley, 1980.
179
1 —^ ^
V — —N^ V
1 V ^^
1 V
-
11i — ' — 11
^_^
>—
^ ,_^
in ix^
,_^
cn CM =r C7^
C\J CM -=r
^ .=r
o ^
t^ ^ O
C^
CM
•« CV~I <o ^T
^~^
CD
CNJ
C3^
^-
o>
CO
[—
m
v£)
v£)
,
O C^ • VO o> C7^
c CJ^ <7^ CT^ •
rt
TD C-
•
—
CM
OO
^
ro
O
CO
c ^ on s^^ V ^
D - ,.' •^ v_^
X3 CO 1— t-
CO o
CD
o
J-
o m
+J ^ m m CD
c .-^
CD ^^ C^
O /-— OJ ^ N y— • • —
i- in ,— ^=r ^3" o-
q; ,
o • •
Q. o CXD '- o o
CJ>
1
— •.
o ,—
•> •>
T—
•» .:q-
^
•h
LPl v£)
D •*
on on ,
t^ xr
E
rt
o
T—
c^
o
m
o
o
o
C3>
• t~-
1 1 ^r o o o CO CTN
CM
CO
m
o •
,—
^
m
T
in
t
CM
cn
03 (\J N ^ N_^ ^^^ t-t s_^
E CO
^-^ CD o 2: ffl
CO
X CN
m OJ r-, ^ ^ m ^-^
(D
Q. ^— ,-— ,'^ ,— ,—
O
o ^-v ^-^ ^-N
^
^-~.
o CM o O LTl /^ o
4J -— CO C7^ CO •
cn o
o c^ • • • •
o CM
O o LTi LTl • ,
m
M <^ CT^
»"
CXD
<J^
o^
C7^
a^
CTn
o
"—
o C7^ C— o
LTl
jj
c^
CT^ *< * •« ^ ^ cn
^
» t-
^
LO
^
•k
^
^
c ^3- O
O
C~- ,— o CTN
^
vO ,— CO m .a-
CO
^ cn
^ o>
<M o
o
CY-1
a>
^r
-3"
co c— m
l>- O
CM
CO
VO
CO
,
o
C^
S- tX3 ,
o o o> CJ> <7^ c- t— CTN c^ •
o t- O o o o> o> • cr^ a^ • . <o

ex o • • • • • !>- • • =r CO CM
E
•^
o •
o
t—
CM
T—
-=r
r—
in
^—
OD
T— —
CM o
cn
r—
0-)
cn
— >-
^—
,—
-
•v„^ ^—^ ^— ^-^ v*^ x^ V—

o —
T
iH 1— t. 1—
t. CQ o 2 o li, CO cu CO o CQ r-
o :i: o CSI J- ID 01 CO CM m (T) CM
s "* '^ ^ '^ ^ ^ CM m m cn t^ "
<4-<
o m
0)
=ifc Q,
r-i
o
JJ
cn ^ I>- t- CO v^ CO ^- o
,
^
,
I^
,
cn
CM
CO O
4J CO
O -rH
E-
CO
D
c c Q) iL 0)
-!-> Q> 0) C c O c (D
C hO c bO c •M o i: i- •iH C Q)
CD O C o o <D I- o ex D su •M c
E S- o Xi J_ bO o •r-4 CO Cm o E M
(U TD t. C- Jj >, D .-< o r— r— O •o
iH >> o CO 1-1 X r— •r-l
x: 3 x: i. o
W a: m o 2 o tL. CO D_ CO o CQ 1—
180
Rules for Determination of Molecular Formula
The following rules are used in the mass spectroscopic determination of
the molecular formula of an organic compound [1 ]. These rules should be
applied to the molecular ion peak and its isotopic cluster. The molecular
ion, in turn, should be the highest mass in the spectrum, must be an
odd-electron ion and must be capable of yielding all other important ions of
the spectrum via a logical neutral species loss. The elements that are
assumed to (possibly) exist are carbon, hydrogen, nitrogen, the halogens,
sulfur and/ or oxygen. The molecular formula that can be derived is not the
only possible one and consequently help from nuclear magnetic resonance
spectrometry and infrared spectrophotometric data is necessary for the final
determination.
Rule 1 : An odd molecular ion value suggests the presence of an odd number of
nitrogens. An even molecular ion is due to the presence of zero or
an even number of nitrogens. Thus, m/e = 141 suggests 1, 3. 5, 7,
etc., nitrogen atoms while m/e = 142 suggests 0, 2, 4, 6, etc.,
nitrogen atoms.
Rule 2 : The maximum number of carbons can be calculated from the formula
Relative Intensity of M + 1 100

Relative Intensity of M 1.1
where M + 1 is the peak next to that of the molecular ion (M"^). This
rule gives the maximum number of carbons, but not necessarily the
right number. Thus, if for example the relative intensities of M"^
181
and M + 1 are 100? and 9% respectively, then the maximum number of
carbons is
9 100
X
100 1.1
There is a possibility for seven, six, etc., carbons but not for
nine or more.
Rule 3 • The maximum numbers of sulfurs can be calculated from the formula
Relative Intensity of M + 2 100

Relative Intensity of M"^ ^ 4.4
where M + 2 is the peak next to that of the molecular ion M"^.
Rule 4 ; The number of chlorines and/or bromines can be derived from the table
showing the relative ratio of the isotope cluster of the molecular
ion.
Rule 5 : The difference should be only oxygen and hydrogen. These rules
assume absence of phosphorus silicon or any other elements.
REFERENCE ;

182
Chlorine - Bromine Combination Isotope
Intensities
Due to the distinctive mass spectral patterns caused by the presence of
chlorine and bromine in a molecule, interpretation can be much easier if the
results of the relative isotope concentrations are known. The following table
provides peak intensities (relative to the P"^ at an intensity normalized to
100 percent) for various combinations of chlorine and bromine molecules,
assuming the absence of all other elements except carbon and hydrogen [1-3].
The mass abundance calculations were based upon the atomic mass data of Weast
[4].
REFERENCES ;
[1 ] McLafferty, F.W., Interpretation of Mass Spectra , University Science

[2] Silverstein, R.H., G.C. Bassler and T.C. Morrill, Spectrometric

Identification of Organic Compounds John Wiley and Sons, New York, 1981
,
[3] Williams, D.H. and I. Fleming, Spectroscopic Methods in Organic

Chemistry McGraw-Hill, London, 1973-
,
[4] Weast, R.C., ed.

Handbook of Chemistry and Physics. 63rd. Ed.
, , The
Chemical Rubber Company, Boca Raton, 1984.
183
Relative Intensities of Isotope Peaks for Combinations of
Bromine and Chlorine (P"^ = 1005^)
Bro Bri Br2 Br3 Bri4
P + 2 98.0 196.0 294.0 390.8

Clo P + 4 96.1 288.2 574.7
P + 6 94.1 375.3
P + 8 92.0
P + 2 32.5 130.6 228.0 326.1 424.6

P + 4 31.9 159.0 383.1 704.2
Cli P + 6 31.2 187.4 564.1
P + 8 30.7 214.8
P + 10 30.3
P + 2 65.0 163.0 261 .1 359.3 456.3

P + 4 10.6 74.4 234.2 490.2 840.3
CI, P + 6 10.4 83.3 312.8 791.6
P + 8 10.2 91.7 397.5
P + 10 9.8 99.2
P + 12 10.1
P + 2 97.5 195.3 294.0 393.3

P + 4 31 .7 127.0 99.7 609.8
P + 6 3.4 34.4 159.4 473.8
C13 P + 8 3.3 37.1 193.9
P 10
+ 3.2 39.6
P + 12 3.0
P + 14
P + 2 130.0 228.3 326.6 4.2

P + 4 63.3 190.9 414.9 735.3
P + 6 13.7 75.8 263.1 670.0
C14 P + 8 1.2 14.4 88.8 347.1
P + 10 1.1 15.4 102.2
P + 12 1.3 16.2
P + 14 0.7
184
Relative Intensities of Isotope Peaks for Combinations of
Bromine and Chlorine (P"*" = 100^)
Bro Bri Br2 Br3 Br4
P + 2 162.6 260.7 358.9

P + 4 105.7 265.3 520.8
P + 6 34.3 137.9 397.9
Cl^ P + 8 5.5 39.3 174.5
P + 10 0.3 5.8 44.3
P + 12 0.3 5.7
P + 14 0.5
P + 2 195.3
P + 4 158.6
Cl6 P + 6 68.8
P + 8 16.6
P + 10 2.1
P + 12 0.1
P + 2 227.8
P + 4 222.1
P + 6 120.3
CI7 P + 8 39.0
P + 10 7.5
P + 12 0.8
P + 14 0.05
185
Common Fragmentation Patterns of Families
of Organic Compounds
The following table provides a guide to the identification and
interpretation of commonly observed mass spectral fragmentation patterns for
common organic functional groups [1-4]. It is of course highly desirable to
augment mass spectroscopic data with as much other structural information as
is possible. Especially useful in this regard will be the confirmatory
information of infrared and ultraviolet spectrophotometry and nuclear magnetic
resonance spectrometry.
REFERENCES
[1 ] Pasto, D.J. and C.R. Johnson, Organic Structure Determination .
Prentice-Hall, 1969.

Books, 1980.
[3] Rose, M.E. and R.A.W. Johnstone, Mass Spectrometry for Chemical and
Biochemists , Cambridge University Press, 1982.
[4] Silverstein, R.M., G.C. Bassler and T.C. Morrill, Spectrometric

Identification of Organic Compounds, John Wiley and Sons, 1981.
186
—V VV
iH c Cm g
CO tlH O >> CO •'H Q
C O X2 rH 4-5 £- Cm
•H L ,-{ CD CD <4-l O
bO CO CO CO £1 bO
o + u •H --'CO C
^^
r-l CO CO
t. o o O > C o >.
O rH a: ti-. CD CT^ C CO o •H 4-5
CX CM O CD •H 4-5 L •
•- X5 rH C
(D
x: ^ t.
O X d::
"^H- CO
<D II
L O >.
CO
e '^ o
E E o:0 Cm •H
CO
J-)
•o
CO
r< i.
^X (LJ .^^
« CD
-^
CO
O CO
4J
•rH
CO •
S-
O
Cm J
CO 4J
CO
^ c O
C ^-' ^ CE CO E CO (D C CO O 4J
03 D (0 cv^ CD x: XD c •« s: c
Q) O x: II CX jJ> CX 4J •H
Cu J- O t. CO rH CO c CO CO S
ctS 0) 3 CD
11
^ 8 -rH •H x;
1
C-H hO
O E O CD \ ^ > o N >
X ^ Cm
. CO
Cm \ E
1
•iH CO
O
CO S (0 o 5 J-
J-> •o E rH Jj) 4JI o C
CO C rH x: -p o bO £3. c rH o o c
•rH O rH JJ JJ (0 X^ c -a CD •H L f^
L
q;
JD O -rH
>, 3
CO
^ O
O
O bO CD E
L c x: CD
• •^
CO CO
rH
XC-O
x:
4-> o O (0 rH ^ 4^ O O bO o •o 3 tJ rH
o >> CO CD CO CO L CO C c c E <
(0
tn
o1
>, rH CD D.
£1 CO ex o
V-- 4->
CO
4J
4J
CO CO CO L C
O O
1
CO
t. £h
Cfl o» 3 4-) CO C CO c • X3 ^— Cm •H rH
j:: >> O C -!-> CD - CO 4-5 N 4-5
o Di: rH (D C CD L bO'-^ C CD c Cm X r-t •H -H
rH C CD C O O CO -H tn • O o CO CO Q
•••
o1
CO CO C -H C|_i L CD to ^ CO ^— •
II J- O
CO 3 4-3 -H S a>5 -a>> sz >-> CM 4-5 CO (N Q. O
4-5 •. CO rH E O+ O jj S-, X C 4J X C E C-
C o 3 3 O L X x: x: ^ <x CJ> •H C o O 4J
0) E S- Ci.:o CD <M CD o bO o
s
1
CJ) • 1 -rH CX ON O -a O Cm CO Cu E SL.

bO c CO .- •M rH Cm •H CO CO Cm
rt ^ o oN C .. CO cd XJ CO CO CO 4-5
H
bO 4^ o x: •«
S- .H £) CO rH >> CO J c x: C •H 4J '-
L X Cm O rH x: o o o c c
Dl, (0
CO
Cw O
^ -rH
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191
VII. Tables for
Qualitative Analysis
193
Organic Group Qualitative Tests
The following flow charts and notes provide a step by step process for
the identification of functional groups which may be present in an unknown
sample [1-7]. These are meant to augment and confirm information obtainable
using instrumental methods pf analysis. It will usually be necessary to use
gas or liquid chromatography before these "wet" chemical tests in order to
determine the number of components present in a given sample. Since many of
these tests require the use of dangerous compounds, the strictest rules of
laboratory safety must be observed at all times. The use of a fume hood is
required.
Note: ppt = precipitate
cone = concentrated
dil = dilute
REFERENCES:
[1 ] Paste, D.J., Johnson, C.R., Laboratory Text for Organic Chemistry ,
Prentice Hall, Englewood Cliffs, 1979.
[2] Sarlo, E. Svoronos, P.D.N.

, Experiments for Organic Chemistry
, , Burgess
Publishing, Minneapolis, 1983.
[3] Roberts, R.M., Gilbert, J.C., Rodewald, L.B., Wingrove, A.S., An

Introduction to Modern Experimental Organic Chemistry Holt, Rinehart, ,
and Winston, New York, 1969.
[4] Hopkins and Williams Research Laboratory, Organic Reagents for Organic
Analysis Chemical Publishing Co., Brooklyn, 1946.
,
[5] Hodgman, CD., Weast, R.C., Selby, S.M., Tables for Identification of
Organic Compounds Chemical Rubber Publishing Co., Cleveland, 1950.
,
[6] Kam.Ti , 0., Qualitative Organic Analysis , John Wiley and Sons, Inc., New
York, 1932.
195
[7] Vogel, A. I., A Textbook of Practical Organic Chemistry , Longmans, Green,
and Co., London, 1951.
196
Protocol For Chemical Tests
Ceric ammonium nitrate : To 1-2 ml 5% eerie ammonium nitrate add 10 drops of
the compound to be tested. A change to an orange/red color is indicative of
an alcohol (detection limit 100 mg - compounds tested Ci-C-iq)-
Dichromate test ; Add ten drops of the alcohol to be tested to a mixture of
1 ml ^% Na2Cr20y and 5 drops cone. H2SO14. A blue-green solution is positive
test for a 1 ° or 2° alcohol. 3° alcohols do not react and, therefore, the
solution stays orange. (Detection limit 20 yg - compounds tested C-i-Cg).
2,4-Dinitrophenylhydrazine test (2,4-DNP) : Add 10 drops of the compound to be
tested to 1 ml of the 2,4-DNP reagent. A yellow to orange-red ppt is
considered a positive test. The 2,4-DNP reagent can be prepared by dissolving
1 g 2,4-dinitrophenylhydrazine in 5 ml cone. H2SO11 and then mixing it with
8 ml of water and 20 ml 95X ethanol. The solution should be filtered before
reacting it with the unknown compound. (Detection limit 20 pg - compounds
tested C-i-Cg) .
Ferric chloride test : Add 10 drops of 3% aqueous FeCl^ solution to 1 ml of a
5% aqueous (ethanol) solution of the compound in question. Phenols give red,
blue, purple or green colorations. The same test can be done by using
chloroform as a solvent (detection limit 50 yg).
Hinsberg test : To 0.5 ml of the amine (0.5 g, if solid) in a test tube add
1 g of p-toluenesulfonyl chloride and 8 ml ^0% NaOH. Stopper the tube and
shake for 3~5 minutes. Remove the stopper and warm the tube with shaking in a
197
hot water bath (70°C) for about one minute. No reaction is indicative of a 3°
amine, which is usually soluble upon acidification (pH = 2--4) with 1 0X HCl.
If a precipitate is present in the alkaline solution, dilute with 5-8 ml H2O
and shake. If the precipitate does not dissolve the original amine is,
probably, a 2° one. If the solution is clear acidify (pH = M) with 10? HCl.
The formation of a precipitate is an indication of a 1

° amine. (Detection
limit 100 mg - compounds tested C-j-C-ig.)
Iodoform test : The reagent calls for the mixture of 10 g I2 and 20 g KI in
100 ml water. The reagent is then added dropwise to a mixture of 10 drops of
the compound in question in 2 ml of water (or dioxane, to facilitate the
solubility) and 1 ml 10? aqueous NaOH solution until a persistent brown color
remains (even when heating in a hot water bath at 60°C.) A yellow precipitate
is indicative of iodoform (CHIo) formation and is characteristic of a methyl
ketone, acetaldehyde or an alcohol of the general formula CH^CHOH (R = alkyl,
R
hydrogen). Aldols (R-C-CH2-CH-R' ) also give a positive iodoform test by a
II I
OH
retro aldol condensation first yielding R-C-CHo + R'-C-H (detection limit
II II
1 00 mg).
Lucas test : The reagent is made by dissolving 16 g anhydrous ZnCl2 in 10 ml
cone. HCl with cooling to avoid HCl loss. Add 10-15 drops of the alcohol to
2 ml of the reagent. 3° alcohols form an emulsion (the alkyl halide) almost
immediately, 2° alcohols form it after 2-5 minutes while 1 ° alcohols react
after a very long time.
Sodium fusion test : 10 mg of the compound to be analyzed are mixed with a
fresh piece of sodium metal of the size of a small pea in a 4-inch test tube.
198
The test tube is warmed gently until melting of the sodium metal and
decomposition (indicated by charring) of the compound occurs. When it appears
that all the volatile material has been decomposed, the test tube is strongly
heated until the residue becomes red. After 3 minutes of constant heating,
the mixture is left to cool ^to room temperature, then a few drops of methanol
are added. If no smoke appears, an excess of sodium metal was not present and
incomplete conversion of the elements (N, S, halogens] to their anions (CN~,
S~^ , halides) is very likely. Addition of another tiny piece of sodium metal
and repetition of the heating process is necessary. If smoke appears then the
test tube is plunged in a small beaker containing 10-15 ml distilled water and
covered with a watch glass or a wire gauze. The test tube might shatter and,
therefore, having the small beaker inside a larger one is recommended. The
contents of the test tube together with the broken glass are ground in a
mortar using a pestle, then transferred in the small beaker and heated for a
few minutes. The solution is then filtered and the solution divided into two
larger parts and one 1 -ml part.
Detection of nitrogen ; To one of the larger parts add 0.5 ml of 6M NaOH
(pH adjusted to 13), five drops of saturated Fe(NHi|)2(S04)2 and five drops 307°
KF solution. The mixture is boiled for 30 seconds and immediately acidified
with 6M H2SO21 with stirring until the colloidal iron hydroxides are dissolved.
The formation of a blue color is indicative of the presence of nitrogen,
presence.
Detection of sulfur : To the 1-ml part add 10 drops of 5M acetic acid and
2-3 drops of 5% lead acetate solution. A black precipitate is indicative of
sulfur presence.
199
.
Detection of halogens : To the other larger part add ]0% H2S0i| until the
solution is acidic. Boil off the solution to 1/3 its volume to secure
evaporation of H2S and HCN gases. Formation of a precipitate upon addition of
10% AgNO^ solution is indicative of the presence of a halogen - white for a
chloride (which is soluble in 6M NHijOH), pale yellow for a bromide (which is
only slightly soluble in 6M NHi(OH) and canary yellow for iodide (which is
insoluble in 6M NH4OH). Should the color of the precipitate be difficult to
provide satisfactory identification of the halogen, proceed as follows: the
working solution which has been acidified with ]0% H2SO14 and boiled down is
treated with 4-5 drops 0.1 N KMnOij solution, with enough oxalic acid added to
discharge the color of excess permanganate and 0.5 ml carbon disulfide. The
presence of a color in the carbon disulfide layer indicates the presence of
bromine or iodine - purple if iodine is present, red-brown if bromine is
present, colorless if chlorine is present. Should the compound to be tested
carry both bromine and iodine the identification will be difficult (red-brown
to purple carbon disulfide layer). Addition of a few drops of allyl alcohol
decolorizes bromine but does not decolorize iodine.
Tollen's test : The reagent is actually made by mixing two solutions (A and B)
Solution A is a 10^ aqueous AgNO^ solution and Solution B is a 10^ aqueous
NaOH solution. When the test is required, one ml of solution A and one ml of
solution B are mixed, and the silver oxide thus formed is dissolved by
dropwise addition of 10^ aqueous NHijOH. To the clear solution, 10 drops of
the compound to be tested are added. A silver mirror is indicative of the
presence of an aldehyde. The reagent mixture (A + B) is to be prepared
immediately prior to use, otherwise explosive silver fulminate might be formed.
200
The silver mirror is usually deposited on the walls of the test tube
immediately or after a short warming period in a hot water bath. It is to be
disposed of immediately with water and/or dil. HNO^. (Detection limit 50 mg -
compounds tested C-1-C5.)
201
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206
Inorganic Group Qualitative Tests
The following tables list some simple chemical tests which will indicate
the presence or absence of a given inorganic cation or anion [1]. For most of
these tests, the anion or cation must be present at a relatively high
concentration (approximate lower bound is 0.05 percent). It may therefore be
necessary to concentrate more dilute samples before successful results can be
obtained. These tests should be used in conjunction with other methods such
as the chromatographic methods or spectrometry and spectrophotometry. Since
many of these tests require the use of dangerous compounds, the strictest
rules of laboratory safety must be observed at all times. The use of fume
hood is required.
REFERENCES ;
[1 ] Barber, H.H., Taylor, T.I., Semimicro Qualitative Analysis . Harper
Brothers, New York, 1953.
207
) )
gives
acids,
i-i C yellow
liberate
c precipitate
4-:
all renders C
00 r-^
E-
solution
c
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bO
p
dirty
E-
solutions (brown) solutions CO S
rJ which yellow a
<
M
cloudy KMn04
precipitate
•H
cc
of
o salt
bO ct
gives
cc
KI
CX •a a
oo CO2
Pb
H j-
Effervescence
s c deposit
CO CO give
from decolorize
limewater
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giving
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black
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s- 2.
I2 ClH 4J
J-
o
00
,
a:
CO2 00
•o
NO2 SO2
CD
4->
CO
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4-i CO
c liberating
(odorless
Liberate Liberate
(pungent
CD (brown)
O JD
C •H
o J
o
00
00
soluble
heating in
o
M precipitate,
•a; o yellow
upon
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c
3
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CL3
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(slow)
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-0
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CC
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217
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Flammability Hazards of Common Liquids
The following table lists relevant data regarding the flammability of
common organic liquids [1,2].
REFERENCES;
[1 ] Turner, C. F., McCreery, J. W., The Chemistry of Fire and Hazardous

Materials , Allyn and Bacon, Boston, 1981.
[2] E.I. du Pont de Nemours & Co., Inc., Data Safety Sheet, Wilmington,
Delaware, 1985.
Auto-
Boiling Flash ignition How to
Specific point point point extinguish
Solvent Formula gravity (°C) (°C) (°C) flames
acetaldehyde CH3CHO 0.8 21 -38 185 a.bsC
acetone (CH3)2C0 0.8 57 -18 538 a,b
acetonitrile CHjC^N 0.79 82 6 a,c,d
acetylacetone CH3COCH2COCH3 1 .0 139 41 — a,b,c
acrolein CH2=CHCH0 0.8 53 -26 277 a,b,c
acrylonitrile CH2=CH-CHC=N 0.81 77 481 a,c,d
allylamine CH2=CHCH2NH2 0.8 53 -29 374 a,b
amylmercaptan CH3(CH2)^SH 0.8 127 18 a,b
aniline CeH5NH2 1 .0 184 70 768 a,b,c

use masks
anisole CeH50CH3 1 .0 15^1 52 a,b,c
benzaldehyde CgHsCHO 1 .1 179 65 192 a,b,c
benzene CeHs 0.88 79 -11 563 a,b,c
bromine Br2 3.0 59 — CO2 (never

H2O)
butyl alcohol C^HgOH 0.8 117 29 366 a,b,c
a - alcohol foam, b - carbon dioxide,

c - dry chemical, d - water
221
Flammability Hazards of Common Liquids (cont.)
Auto-
t-butylperacetate CH3C0(02)C(CH3)3 <27 b,c
t -butyl per ben zo- CsH5C0(02)C(CH3)3 >1 .0 112 88 8 a,b,c

ate
butyraldehyde CH3(CH2)2CH0 0.8 76 7 230 a,b,c
carbon disulfide CS2 1.3 47 -30 100 b,d,

use masks
crotonaldehyde CH3CH=CHCH0 0.9 10^4 13 232 a,b,c
cumene hydro- 1 .0 153 175 a,b,c

peroxide
cyclohexanone 0° 0.9 156 143 420 a,b,c
diacetyl (CH3C0)2 1 .0 88 27 a,b,c
diethanolamine (H0CH2CH2)2NH 1 .1 269 152 662 b ,c
diethylene glycol CH3(CH20CH2)3CH3 0.9 189 83 a, halons

diethylether
diethylether (C2H5)20 0.7 34 -45 180 a,b,

halons
diethylketone (C2HJ2CO 0.8 101 13 452 a,b,c
dimethyl sulfate (CH3)2S0^ 1.3 188 83 188 a,b,c,d
dimethyl sulfide (CH3)2S 0.8 37 -18 206 b,c
,4-dioxane .0 101 2 180 a,b,c

1
< > 1
ethanol C2H50H 0.8 78 13 423 a,b,c
ethylacetone CH3COCH2CH2CH3 0.8 102 7 504 a,b,c

(2-pentanone
ethylamine C2H3NH2 0.7 31 -18 384 a,b,c

222
Auto-
Specific point point point extinguis h
ethylenediamine H2NCH2CH2NH2 0.9 117 34 385 a,b,c
ethyleneglycol HOCH2CH2OH 1 .1 198 1 1 1 413 a,b,c,d
formaldehyde HCHO 1 .0 99 88 427 a,b,G
furfural r>Ho 1 .2 162 60 316 a,b,c,d
furfuryl alcohol ^3^H20H 1 .1 171 75 491 a,b,c
gasoline C7H16 (isomers) <1 .0 38-218 -43 257 a,b,c
hexylamine C6H13NH2 0.8 132 29 a,b
isopropanol (CH3)2CH0H 0.8 82 12 399 b,c
isopropyl ether ((CH3)2CH)20 0.7 68 -28 443 a,b
kerosene CH^ series <1 .0 149-316 38-71 229 a,b,c

mixture
methanol CH3OH 0.8 65 1 1 464 a,b
methylamine (aq) CH3NH2 0.7 31 -18 384 a,b,c
methylaniline CH3NHC6H5 0.8 151 49 533 a,b
methylethyl CHaCOCHjCHa 0.8 79 -6 516 a,b,c

ketone
methylethyl C.H3O2 63 a,b

ketone peroxide
naphtha (mixture) 0.8-0.9 149-216 38-46 277-496 a,b,c
paraldehyde 1 .0 124 36 238 a,b,c
CH3

223
Auto-
2-pentanone See Ethylacetone
3-pentene nitrile CH3CH=CHCH2C=N 0.83 U.5 40 b,c,d
peracetic acid CH3CCOOH 1 .2 105 40 a,b,c
petroleum ether <0.7 38-79 <0 288 a.b.c
propionaldehyde CH3CH2CHO 0.8 49 8 207 a,b, c
propylamine . CH3CH2CH2NH2 0.7 49 -37 318 a,b,c
propy].ene glycol CH3CHOHCH2OH 1 .0 188 99 421 a,b
sulfur chloride S,C1, 1 .7 138 118 234 b,c
sulfur yl chloride SOCI2 1 .7 69 — a,b,c
tetrahydrofuran -17 a,b,c

C/ 0.9 60 321
th i on yl chloride SOCI2 1 .6 79
toluene CSH5CH3 0.87 111 4 510 a,b,c
triethanolamine (H0CH2CH2)3N 1 .1 360 179 b,c,d
triethylamine (C2H5)3N 0.7 89 7 a,b,c
xylene (o-) CeHjCH3)2 0.88 144 32 463 a,b,c
xylene (m-) C.E.iCE,)^ 0.86 139 29 527 a,b,c
xylene (p-) CeH,(CH3)2 0.86 138 39 529 a,b,c

224
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Hazardous Material Log Sheet
The many chemical hazards present in the analytical laboratory must be
subject to strict control. To assist in this vital function, a log sheet for
each hazardous compound is helpful. The following example, adapted from that
suggested by Pfaff [1], is currently used in the analytical laboratory of the
Thermophysics Division (774.03) of the National Bureau of Standards, Boulder
Laboratories.
[1] Pfaff, R.C., J. Chem. Educ, 62, A282, 1985.
Analytical Laboratory
Hazardous Materials Log Sheet
Name of Material:
Date of Receipt: Name of Receiver:
Quantity: Container Size:
Form of Shipment (i.e.. Federal Express, UPS, etc.):
Condition of Shipment or Sample:
Distribution of Material: Amount: Building:
Room Number: Name of Principal Investigator:
Date: Signature of Recipient:
Exact Storage Location:
Material Safety Data Sheet Available: Yes No
Approved Safety Plan Available: Yes No
Disposal: Amount: Date: Program:
Disposal Data:
Health and Safety Impact:
229
Unit Conversions
The international system of units is described in detail in NBS Special
Publication 330 [1 ] and lists of physical constants and conversions factors
are tabulated by Mechtly [2]. The American Society for Testing and Materials
(ASTM), American National Standards Institute (ANSI), and Institute of
Electrical and Electronics Engineers (IEEE) have published a joint standard
for metric practice [3]- The most recent guidelines for use of the metric
system are given in References 1, 2 and 3. Selected unit conversions are
given in the following tables.
References :
[1 ] The International System of Units, National Bureau of Standards (U.S.)

Special Publication SP-330 (Aug. 1977).
[2] Mechtly, E.A., The International System of Units, Physical Constants and
Conversion Factors, NASA Special Publication SP-7012, 1964.
[3] Standard for Metric Practice, ANSI/ASTM E-38O-76, IEEE Std. 268-1975 (Jul
1976).
230
Density
kg/m^ g/cm^ Amagat Ib/ft^
16.018 0.016018 178.216 1
1 0.001 11 .126 0.062^128
1,000 1 1 .1126 X 10'' 62.i]28
2,015.9 2.0159 2.2il28 X 10" 125.85
0.089881 8.9881 X 10"^ 1 5.61 11 X 10"'
Specific Volume
mVkg
(L/g) cm'/g ft Vlb
0.062428 62.428 1
1 1 ,000 16 018
0.001 1 0.016018
4.9605 X lO"'' 0.49605 7 9458 X 10"'
Pressure
Torr lbs/in,
MP a atm (mm Hg) bar (psi)
6.8948 X 10"' 0.068046 51 .715 6.8948 X 10"2 1
1 9.8692 7,500.6 10.0 145.04
0.101325 1 760.0 1.01325 14.696
1 .3332 X 10"* 1 .3158 X 10"' 1 1.332 X 10"' 0.019337
0.1 0.98692 750.06 1 14.504
231
Enthalpy , Heat of Vaporization , Heat of
Conversion, Specific Energies
kJ/kg
(J/g) cal/g Btu/lb
2.3244 0.55556 1
1 0.23901 0.43022
0.49605 0.11856 0.21341
4.1840 1 1.8
Specific Heat, Entropy
kJ/kg-K
(J/g-K) Btu/°R
4.184 1
1 0.23901
0.49605 0.1 1856
2.0755 0.49605
Thermal Conductivity
mW/cm-K J/s-cm-K cal/s-cm-K Btu/ft-hr-°R
17.296 0.017296 0.0041338 1
1 0.001 2.3901 X 10""* 0.057816
1 ,000 1 0.23901 57.816
4,184 4.184 1 241 .90
232
Viscosity
kg/m-s Centipoise Ib-s/ft^

(N-s/m^) (10"^g/cm-s) (slug/ft-s) Ib/ft-s
1.48816 1,488.16 0.31081 1
1 1 ,000 0.020885 0.67197
0.001 1 2.0885 X 10"^ 6.7197 X 10""*
47.881 4.7881 X 10"* 1 32.175
Velocity of Sound Surface Tension
m/s ft/s N/m dyne/cm Ibf/in.
0.3048 1 175.13 175.13 X 10^ 1
1 3.2808 1 1 ,000 5.7102 X 10"'
0.001 1 5.7102 X 10"'
Temperature
T(Rankine) = 1.8T(Kelvin)
T(Celsius) = T(Kelvin) - 273-15
T(Fahrenheit) = T(Rankine) - 459.67
T(Fahrenheit) = 1 . 8T(Celsius) + 32
233
NBS-114A (REV. 2-8C)
U.S. DEPT. OF COMM. 1. PUBLICATION OR 2. Performing Organ. Report No, 3. Publ icatlon Date
REPORT NO.
BIBLIOGRAPHIC DATA
SHEET (See instructions) NBS/TN-1096 April 1986
4. TITLE AND SUBTITLE
BASIC TABLES FOR CHEMICAL ANALYSIS
5. AUTHOR(S)
Thomas J. Bruno and Paris D. N. Svoronos
6. PERFORMING ORGANIZATION (If joint or other than NBS, see instructions) 7. Contract/Grant No.
NATIONAL BUREAU OF STANDARDS

DEPARTMENT OF COMMERCE 8. Type of Report & Period Covered
WASHINGTON, D.C. 20234
9, SPONSORING ORGANIZATION NAME AND COMPLETE ADDRESS (Street. City. State, ZIP)
Gas Research Institute

and
United States Department of Energy-
Office of Basic Energy Sciences
10. SUPPLEMENTARY NOTES
[]]J Document describes a computer program; SF-185, FlPS Software Sumimary, is attached.
11. ABSTRACT (A 200-word or less factual summary of most significant information. If document includes a si gnificant
bi bliography or literature survey, mention it here)
Tables of important data for use in the analytical chemistry laboratory are
provided. These tables contain information for use in gas chromatography,
liquid chromatography, infrared and ultraviolet spectrophotometry, mass
spectrometry, and wet chemical techniques. Tables relating to safe practice
in the analytical laboratory are also included.
12. KEY WORDS (Six to twelve entries; alphabetical order; capitalize only proper names; and separate key words by semicolons)
chemical analysis; instrumental analysis.
13. AVAILABILITY 14. NO. OF

PRINTED PAGES
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i-U.S. GOVERNMENT PRINTING OFFICE:1986- 671-586 / 45170
.
T^
M he National Bureau of Standards' was established by an act of Congress on March 3, 1901. The
Bureau's overall goal is to strengthen and advance the nation's science and technology and facilitate
their effective application for public benefit. To this end, the Bureau conducts research and provides: (1) a
basis for the nation's physical measurement system, (2) scientific and technological services for industry and
government, (3) a technical basis for equity in trade, and (4) technical services to promote public safety.
The Bureau's technical work is performed by the National Measurement Laboratory, the National
Engineering Laboratory, the Institute for Computer Sciences and Technology, and the Institute for Materials
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The National Measurement Laboratory

Provides the national system of physical and chemical measurement; • Basic Standards^
coordinates the system with measurement systems of other nations and • Radiation Research
furnishes essentiaJ services leading to accurate and uniform physical and • Chemical Physics
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Provides technology and technical services to the public and private sectors to Applied Mathematics
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Conducts research and provides measurements, data, standards, reference Inorganic Materials
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Basic Tables For Chemical Analysis

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NATL INST.

OF STAND & TECH

U.S. DEPARTMENT OF COMMERCE / National Bureau of Standards

Basic Tables for Chemical

Applied Mathematics — Mathematical

Consumer Information Series —

Basic Tables for Chemical Analysis ^^^

Paris D.N. Svoronos

U.S. DEPARTMENT OF COMMERCE, Malcolm Baldrlge, Secretary

NATIONAL BUREAU OF STANDARDS, Ernest Ambler, Director

Issued April 1986

U.S. GOVERNMENT PRINTING OFFICE

I. Tables for Gas Chromatography 5

Mesh Sizes and Particle Diameters 7

Gas Chromatographic Support Materials 9

Carrier Gas Properties 12

Properties of Some Liquid Phases 15

Stationary Phases for Packed Column Gas Chromatography 33

Silicone Liquid Phases 35

Adsorbents for Gas-Solid Chromatography 48

Porous Polymer Phases 51

Cryogens for Subambient Temperature Gas Chromatography 58

Some Useful Fluids for Supercritical Fluid Chromatography 60

II. Tables For Liquid Chromatography 61

Solvents for Liquid Chromatography 63

Modes of Liquid Chromatography 66

Reverse Phase Materials and Solvents 67

HPLC Column Packings 68

III. Tables for Ultraviolet Spectrophotometry 71

Solvents for Ultraviolet Spectrophotometry 73

Correlation Table for Ultraviolet Active Functionalities 80

IV. Tables for Infrared Spectrophotometry 85

Infrared Optics Materials 87

Wavelength - Wavenumber Conversion Table 91

Useful Solvents for Infrared Spectrophotometry 94

tetrahydrof uran 110

Polystyrene Wavenumber Calibration 112

IR Correlation Chart 113

Infrared Absorptions of Major Chemical Far:ilies 115

Hydrocarbon Compounds 116

Organic Oxygen Compounds 122

Organic Nitrogen Compounds 137

Organic Silicon Compounds 149

Organic Phosphorous Compounds 150

Organic Halogen Compounds 152

V. Tables for Nuclear Magnetic Resonance Spectroscopy 155

Tables for Nuclear Magnetic Resonance Spectroscopy 157

Magnetic Properties of Some Nuclei 158

NMR Correlation Chart 1 59

Proton NMR Absorptions of Major Chemical Families 1 60

Organic Oxygen Compounds 162

Organic Nitrogen Compounds 166

Solvent Positions of Residual (Impurity) Protons

^^C Chemical Shifts of Useful NMR Solvents 174

VI. Tables for Mass Spectrometry 1 77

Natural Abundance of Important Isotopes 179

Rules for Determination of Molelcular Formula I8l

Chlorine - Bromine Combination Isotope Intensities 183

VII. Tables for Qualitative Analysis 193

Organic Group Qualitative Tests 195

Protocol for Chemical Tests 197

Inorganic Group Qualitative Tests 207

VIII. Miscellaneous Tables 21 7