IR Spectral Interpretation

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269-226701, Rev A
Contents
Introduction........................................................................................................... 1
Alcohols................................................................................................................. 2
Aliphatic Acid Halides ....................................................................................... 4
Aliphatic Aldehydes............................................................................................ 5
Aliphatic Alkynes ................................................................................................ 7
Aliphatic Amides ................................................................................................. 9
Aliphatic Amines ............................................................................................... 11
Aliphatic Amino Acids...................................................................................... 13
Aliphatic Anhydrides ........................................................................................ 15
Aliphatic Esters.................................................................................................. 16
Aliphatic Ethers.................................................................................................. 18
Aliphatic Hydrocarbons ................................................................................... 19
Aliphatic Ketones .............................................................................................. 22
Aliphatic Nitriles ............................................................................................... 24
Aliphatic Nitro Compounds ............................................................................. 26
Aliphatic Phosphorous Compounds............................................................... 27
Aliphatic Quinones............................................................................................ 29
Aliphatic SO Compounds ................................................................................. 30
Aliphatic Thiols/Mercaptans .......................................................................... 32
Amine Salts......................................................................................................... 34
Aromatic Acid Halides ..................................................................................... 35

Aromatic Anhydrides ........................................................................................ 36
Aromatic Benzaldehydes ................................................................................. 37
Aromatic Benzamides....................................................................................... 38
Aromatic Esters.................................................................................................. 40
Thermo Scientific Infrared Spectral Interpretation i

Contents
Aromatic Ethers ..................................................................................................42
Aromatic Halide Carboxylic Acid Salts.........................................................43
Aromatic Hydrocarbons ....................................................................................44
Aromatic Mercaptans........................................................................................47
Aromatic Nitriles................................................................................................48
Aromatic Nitro Compounds..............................................................................50
Aromatic Phenones............................................................................................51
Aromatic SO Compounds ..................................................................................53
Benzoic Carboxylic Acids ................................................................................55
Carboxylic Acids ................................................................................................56
Carboxylic Acid Salts........................................................................................58
Halides..................................................................................................................60
Heterocyclics......................................................................................................62
Inorganic Carbonate ..........................................................................................64
Inorganic Nitrates ..............................................................................................65
Inorganic Nitrites ...............................................................................................66
Inorganic Phosphates........................................................................................67
Inorganic Sulfates..............................................................................................68
Kaolin Clays / Alumino Silicates.....................................................................69
Mono Substituted Anilines...............................................................................70
Olefins...................................................................................................................71
Perfluorinated Alkanes .....................................................................................74
Silicon Organics.................................................................................................75
Trifluoromethane Sulfonates ...........................................................................77
ii Infrared Spectral Interpretation Thermo Scientific

Introduction
This document provides a list of compounds that may be present in
mixtures analyzed by Fourier Transform Infrared (FT-IR) spectroscopy.
For each compound, we provide descriptions of the functional groups that
might be present and the approximate locations and intensities of their
absorption bands. The knowledge base can help you determine functional
group types in complex mixtures.
Thermo Scientific Infrared Spectral Interpretation 1

Alcohols
Alcohols
General section for: Aliphatic Alcohols
Aliphatic Diol Alcohols
Phenols
Polyethylenes
Poly(1-Alkenes)
Polypropylenes
Secondary Alcohol Hindered
Tertiary Alcohol Hindered
Tertiary Aliphatic Alcohols
Alcohol Chemical Alcohols are compounds which contain the hydroxyl (-OH) group. These
Properties compounds are classified as primary, secondary or tertiary according to the
number of other carbon atoms attached to the oxygen bound carbon.
Alcohols contain the very polar -OH group. This allows hydrogen bonding
between molecules in the condensed phase. Due to this hydrogen bonding
the boiling points of alcohols are much higher than the corresponding
alkane with the same number of carbon atoms.
-C-O stretching and -OH deformation vibrations
Primary alcohols 1050 cm-1
Secondary alcohols 1100 cm-1
Tertiary alcohols 1150 cm-1
Phenols 1200 cm-1
2 Infrared Spectral Interpretation Thermo Scientific

Alcohols
-OH stretching frequencies Free -OH form
Primary alcohols 3643 - 3630 cm-1
Secondary alcohols 3635 - 3620 cm-1
Tertiary alcohols 3620 - 3600 cm-1
Phenols 3612 - 3593 cm-1
Phenol Chemical Phenols are a class of aromatic compounds in which one or more hydroxy
Properties groups are directly attached to the benzene ring. In addition to phenol,
there are several important phenol families including the cresols and
xylenols.

Aliphatic Acid Halides
Aliphatic Acid Halides

Chemical Properties Acid chlorides are prepared from the corresponding acids by reaction with
thionyl chloride, phosphorous trichloride or potassium pentachloride.
Because of their reactivity in nucleophilic substitution, acid chlorides are
commonly used as intermediates in the synthesis of many organic
compounds.
Spectral The attachment of a halide to a carbonyl carbon atom results in a shift of

Interpretation the carbonyl absorption to higher frequencies. For example, the compound
acetyl chloride absorbs at 1802 cm-1 while acetyl bromide absorbs at 1812
cm-1. Conjugation of the acid halide with an alpha/beta double bond or
aromatic ring will lower this frequency by about 30 cm-1.

Aliphatic Aldehydes
Aliphatic Aldehydes
General section for: Aliphatic Acrolein Aldehydes
Aliphatic Acroleins
Aliphatic Aldehydes
Chemical Properties The common names for aldehydes are derived from the names of the
corresponding carboxylic acids by replacing the -ic with -aldehyde. The
IUPAC naming is similar to other hydrocarbons with the longest chain
carrying the -C(O)H group considered as the parent structure.
Chain is 5 carbons
IUPAC name = 3-Methylpentanal
Because of their ability to form hydrogen bonds the lower molecular weight
aldehydes are appreciably soluble in water.
Spectral The normal range expected for the carbonyl absorption in alkyl aldehydes
Interpretation is 1740-1730 cm-1. As is generally the case for ketones, the vapor phase
spectra are shifted to higher frequencies (typically about 10-15 cm-1).
Unsaturated aldehydes with the double bond positioned in the alpha-beta
position absorb around 1705-1685 cm-1. Aldehydes conjugated with
aromatic rings absorb in the 1710-1690 cm-1 region.
Halogens adjacent to the aldehyde carbon show the same shift to higher
frequencies found for ketones.

Aliphatic Aldehydes
The aliphatic C-H stretching vibrations are highly characteristic and occur
between 2900 and 2700 cm-1.

Aliphatic Alkynes
Aliphatic Alkynes
General section for: 1-Alkynes
Alkynes Disubstituted
Alkynes, Internal
Alkynes Monosubstituted
Aromatic Alkynes – Terminal Position
Internal Alkynes
Terminal Alkynes
Chemical Properties Alkynes have the general formula CnH<SUB<2< sub>n-2. Then simplest
member of the alkyne family is acetylene which has the formula:
H:C:::C:H m.p. -82 / b.p. -75
The IUPAC naming is based on the closest triply bonded carbon.
CH3-C:::C-CH(CH3)2 chain = Five carbons; 4-Methyl-2-pentyne
Acetylene is the family member of chief industrial importance and is

prepared by the action of water on calcium carbide.
Spectral R-C:::C-R'
Interpretation
The infrared spectroscopic detection of the alkyne triple bond depends on
the substitution. The mono-substituted acetylenes can easily be identified
by the strong -C:::C-H (carbon hydrogen) stretching absorption around
3300 cm-1. In the di-substituted alkyne there are no hydrogens on the triply
bonded carbons and this band is absent. If the substitution is asymmetric
the -C:::C- (carbon carbon) stretching absorption around 2100 cm-1 may
be used as an indicator. If the substitution is symmetric about the alkyne
bond, this absorption will be weak or non-existent.

Aliphatic Alkynes
1-octyne is asymmetric with a hydrogen on the triply bonded carbon.

Therefore the bands around 3300cm-1 and 2100cm-1 are present. 4-
octyne is symmetric with regard to the triple bond with no hydrogen atoms
on the triply bonded carbon. In this case there the characteristic
absorptions are absent.

Aliphatic Amides
Aliphatic Amides
General section for: Aliphatic Primary Amides
Aliphatic Secondary Amides
Aliphatic Tertiary Amides
n-phenyl Amides
Chemical Properties Amides have quite high boiling points because they are capable of strong
intermolecular interactions.
In the laboratory, amides are made by the reaction of ammonia with acid
chlorides or acid anhydrides. Industrially, they are often prepared by
heating the ammonium salts of carboxylic acids.
Spectral NH stretching
Interpretation
Primary Near 3350 - 3180 cm-1
3320 - 3070 cm-1(trans and

Secondary
cis)
CO (amide I)
Primary Near 1650 cm-1
Secondary 1680 - 1630 cm-1
Tertiary 1670 - 1630 cm-1

Aliphatic Amides
NH2 def. (amide II)
Primary 1650 - 1620 cm-1
Amide III
Secondary Near 1270 cm-1

Aliphatic Amines
Aliphatic Amines
General section for: Aliphatic Primary Amines
Aliphatic Secondary Amines
Aliphatic Tertiary Amines
Aniline Compounds
Dialkyl Amines
Monoalkyl Amines
Chemical Properties Amines are classified as primary, secondary or tertiary according to the
number of groups attached to the nitrogen atoms.
Amines are an important class of organic compounds because they show

appreciable basicity. They are named in the following manner.
CH3CH2CH2CHCH3 2-Aminopentane
|
NH2
Spectral NH Stretching
Interpretation
Primary amines 3400 - 3380, 3345 - 3325 (m)
Secondary amines 3360 - 3310 (w)
NH Deformations
Primary amines 1650 - 1590 (s)
Secondary amines 1650 - 1550 (m)

Aliphatic Amines
C-N Stretching
Primary amines 1080 - 1040 (m)
Secondary amines 1180 - 1140 (m)
Tertiary amines not diagnostic

Aliphatic Amino Acids

General section for: Aliphatic Amino Acids
Aliphatic Amino Acid Salts
Chemical Properties Although amino acids are often shown as containing an amino group and a
carboxylic acid group H2NCHRCOOH, many of their physical properties
are inconsistent with this structure.
1. They are non-volatile crystalline solids which decompose on melting.
2. They are insoluble in non polar solvents but are soluble in water.
3. Their aqueous solutions show highly soluble dipole behavior.
Therefore, based on these properties the actual structure is believed to be

dipolar as in +H3N-CHR-COO-.
Spectral
Interpretation
Ester Absorptions NH3+
Stretch 3130 - 3030 cm-1
Deformation 1640 - 1610 cm-1
COOH
Ionic form 1600 - 1560 cm-1
Un-ionized 1754 - 1695 cm-1

Other usually observed bands
Bands near 2000 cm-1 amino acid hydrochlorides
Bands near 1300 cm-1 most amino acids

Aliphatic Anhydrides
Chemical Properties Acetic anhydride is the most common member of this family and is
prepared by the reaction of acetic acid with a ketene, CH2=C=O. The
primary use for this anhydride is in the production of acetate fibers and
vinyl acetate.
Spectral All anhydrides show two carbonyl absorption bands. The frequency and
Interpretation relative intensities of these two bands depend on whether or not the
carbonyls are conjugated and if the compound is cyclic in nature. Typically
for linear anhydrides the bands are at approximately 1810 and 1755 cm-1.
With five member cyclic structures the ring strain causes the frequencies to
shift to about 1860 and 1775 cm-1.
The fact that two carbonyls are seen is a result of the coplanar CO-O-CO
structure which gives rise to symmetric and asymmetric carbonyl
vibrations.

Aliphatic Esters
Aliphatic Esters
General section for: Aliphatic 2-Halogen Non-Acetate Esters
Aliphatic 5-Member Cyclic Lactones
Aliphatic a,b-Unsaturated Esters
Aliphatic Acetate Esters
Aliphatic Acetoacetate Esters
Aliphatic Acrylate Esters
Aliphatic Carbonate Esters
Aliphatic Chloro Formate Esters
Aliphatic Esters
Aliphatic Formate Esters
Aliphatic Gamma-Lactones
Aliphatic Halogen Acetate Esters
Aliphatic Methacrylate Esters
Aliphatic Methyl Esters
Aliphatic Propionate Esters
Alkyl Chloroformates
Esters (general)
Gamma Lactones
Chemical Properties
Spectral
Interpretation
Ester Absorptions C=O Stretch
Saturated 1750 - 1730 cm-1
Unsaturated 1730 - 1715 cm-1

Aliphatic Esters
Vinyl 1775 - 1755 cm-1

Alpha keto 1755 - 1740 cm-1
C-O Stretch
Formate 1200 - 1180 cm-1
Acetate 1250 - 1230 cm-1
Phenolic acetates 1250 - 1230 cm-1
Acrylates 1300 - 1200 cm-1

Aliphatic Ethers
Aliphatic Ethers
General section for: Aliphatic Acetals
Aliphatic Epoxides
Aliphatic Ethers
Aliphatic Methoxy Ethers
Epoxides
Chemical Properties To name an ether, generally the individual names for the two attached
groups are used:
On standing in contact with air, most ethers are converted slowly to

unstable peroxides. Although the peroxides are only present at low levels,
they can cause violent explosions. A red color formed with aqueous ferrous
ammonium sulfate solution indicates the presence of the peroxides.
Spectral The only characteristic absorption in the infrared that can be used to
Interpretation identify the presence of aliphatic ethers is the absorption around 1150-
1050 cm-1. This band is generally broad and strong. The exact position of
this absorption is strongly influenced by adjacent functional groups.
Epoxies (cyclic ethers) generally have a band around 1250 cm-1 which has
been assigned to the carbon-oxygen stretching absorption. Peroxides (R-
OO-R") are not very well characterized in the infrared but a band is often
found in the 890-830 cm-1 region.

Aliphatic Hydrocarbons
General section for: Deuterated Alkanes
Linear, Long Chain Aliphatic Hydrocarbons
Aliphatic Functional Aliphatic groups are found in many compounds that the infrared
Groups spectroscopist is likely to encounter. The most important vibrational modes
are the C-H stretching around 3000 cm-1 and the -CH deformation modes
around 1460 cm-1 and 1380 cm-1. The atoms directly attached to the
aliphatic groups may result in significant shifts from the standard
frequencies. In particular adjacent atoms with high electro negativity will
shift the band locations to higher frequencies.
-CH3 and –CH2 The CH3 asymmetric stretching vibration occurs at 2975-2950 cm-1 while
Stretching the CH2 absorption occurs at about 2930 cm-1. The symmetric CH3
vibration occurs at 2885-2865 cm-1 while the CH2 absorption occurs at
Absorptions about 2870-2840 cm-1.
-CH3 Deformation The CH3 asymmetric deformation vibration occurs at 1470-1440 cm-1.
Absorptions This band is overlapped with the CH2 scissor vibration which occurs at 1
490-1440 cm-1. The symmetric CH3 vibration occurs at 1390-1370 cm-1.
The relative intensities of the asymmetric CH3 and the CH2 scissor bands
can be used as an indicator of their proportions in the molecule.

-CH3 Deformation When there are more than one methyl group on a single carbon the
Absorption Band symmetric CH3 vibration which occurs at 1390-1370 cm-1 becomes split
into two bands. When three methyl groups are on a single carbon (t-butyl)
Splitting a band appears near 1365 cm-1 and a weaker band appears near 1390 cm-1.
When two methyl groups are on a single carbon (isopropyl) bands of
approximately equal intensity occur at near 1390 and 1365 cm-1. The
presence of the t-butyl group can be confirmed by the presence of bands
around 1255 and 1210 cm-1 while the isopropyl group shows bands near
1170 and 1145 cm-1.

-(CH2)n -Rocking When there are four or more CH2 in a row, a rocking absorption is found
Absorption centered at 720 cm-1. This absorption splits into two bands when the
number of adjacent methylene groups reaches about ten methylene groups.

Aliphatic Ketones
Aliphatic Ketones
General section for: Aliphatic Alpha Halogen Ketones
Aliphatic Benzoquinones
Aliphatic Cyclic Pentanones
Aliphatic Gem-Diones
Aliphatic Ketones
Aliphatic Methyl Ketones
Alkyl Aryl Ketones
Diaryl Ketones
Phenyl Ketones
Chemical Properties Aliphatic ketones have the general structure:
Where R and R' are alkyl groups that may be the same or different.
Common names are based on the R groups and IUPAC names are based
on the number of carbon atoms.
Example:
Common name: Methyl Ethyl Ketone

IUPAC: 4 Carbons = butane; 2-Butanone
Spectral Ketones show a strong absorption in the region from 1725-1660 cm-1. This
Interpretation band, usually the most intense in the spectrum, is due to C=O stretching
vibration. The following table gives typical ranges.
Saturated open chain ketones 1725 - 1705 cm-1
Alpha - beta unsaturated 1690 - 1675 cm-1
Aryl ketones 1690 - 1660 cm-1
Diaryl ketones 1670 - 1660 cm-1

Aliphatic Ketones

Aliphatic Nitriles
Aliphatic Nitriles
General section for: Aliphatic Isocyanates
Aliphatic Isocyanides
Aliphatic Isothiocyanates
Aliphatic Nitriles
Aliphatic Thiocyanates
Chemical Properties In this group we have combined a number of C=N and C:::N functional
groups.
CH3CH2CH2C:::N n-Butyronitrile or n-propyl cyanide

CH3CH2CH2CH2-N=C=O Butyl isocyanate
CH3CH2CH2CH2-S=C=N Butyl thiocyanate
CH3CH2CH2CH2-N=C=S Butyl isothiocyanate
Spectral The infrared absorption due to nitrile groups are, as would be expected,
Interpretation found in the triple bond region of 2300-2000 cm-1. In the case of saturated
alkyl nitriles the band occurs between 2260 and 2240 cm-1. For isocyanates
the absorption is in the 2275-2240 cm-1 region.
The C=N stretching absorption for open chain compounds occurs in the
1690-1590 cm-1 region. The alpha/beta unsaturated compounds absorb
between 1660 and 1590 cm-1 and the conjugated cyclic compounds absorb

Aliphatic Nitriles

Aliphatic Nitro Compounds
Aliphatic Nitro Compounds

General section for: Aliphatic Nitrates
Aliphatic Nitrites
Aliphatic Nitros
Chemical Properties In this section we have grouped together the aliphatic nitrogen/oxygen
containing compounds: namely nitrites, nitrates, and nitros. The following
nomenclature is most often encountered for these compounds.
Spectral The nitrite group (R-ONO) has two absorptions in the region of 1645cm-1.
Interpretation Usually the lower of the two bands is the less intense of the pair. In addition,
there is a very strong absorption nitrogen/oxygen stretch around 870cm-1.
Organic nitrates show the asymmetric NO2 stretch around 1649cm-1 and
the symmetric stretch around 1280cm-1. The nitrogen/oxygen stretch is
usually found around 870cm-1.
The nitro compounds show strong absorptions around 1560 and 1390cm-1
with the higher frequency band being the most intense.

Aliphatic Phosphorous Compounds

General section for: Aliphatic Phosphates
Aliphatic Phosphites
Aliphatic Phosphonates
Hexafluorophosphates
Chemical Properties The most common of the phosphorous containing compounds are the
derivatives of phosphoric acids.
Like other esters, phosphates undergo hydrolysis to form the parent acid
and an alcohol.
Spectral
Interpretation
P=O (free) 1350 - 1250 cm-1
possibly as low as 1170 cm-1 (s)
P=O (hydrogen bonded) 1250 - 1115 cm-1 (s)
P-O-C 1050 - 990 cm-1 (s)
P-O-ethyl 1170 - 1150 cm-1 (w) and
1090 - 1010 (m)
P-O-
1200 - 1180 cm-1 (w) and
methyl
1060 - 1010 cm-1 (w)
P-O-P 970 - 900 cm-1 (m)
P-OH 2700 - 2560 (broad medium intensity)

P-H 2455 - 2265 cm-1 (m)
PO2- 1325 - 1090 cm-1 and 1155 - 990 cm-1 (m)
PO3(2-) 1140 - 1060 cm-1 and 1010 - 970 (s)
OPO3(2-) 1125 - 965 cm-1 and 1000 - 960 cm-1 (s)

Aliphatic Quinones
Aliphatic Quinones
Spectral Quinine type ketones give rise to a carbonyl stretch which occurs at
Interpretation approximately 1650 cm-1 due to conjugation. The anthraquinones show
the carbonyl stretching band shifted up to about 1675 cm-1 region.

Aliphatic SO Compounds
General section for: Aliphatic Sulfites
Aliphatic Sulfones
Aliphatic Sulfonic Acids
Aliphatic Sulfonic Acid Salts
Aliphatic Sulfoxides
Chemical Properties
Spectral
Interpretation
Ester Absorptions Sulfur-Oxygen Assignments
C-SO-C 1070-1035 cm-1 (s)

O-SO-O Near 1225 cm-1 (s)
N-SO-N Near 1120 cm-1 (s)
S-SO-S Near 1105 cm-1 (s)
C-SO2-C 1330-1305 cm-1 (s)
C-SO2-NR2 1360-1335 cm-1 (s)
1170-1150 cm-1 (s)
C-SO2-OR 1380-1350 cm-1 (s)
1190-1180 cm-1 (s)
R-OSO2-OR2 1415-1380 cm-1 (s)
1190-1175 cm-1 (s)

R-SO3-Na 1190-1175 cm-1 (s)

1065-1060 cm-1 (s)

Aliphatic Thiols/Mercaptans
Chemical Properties The aliphatic R-SH compound is named as either a thiol or a mercaptan.
CH3CH2CH2CH2CH2SH
1-Pentanethiol or n-Pentyl mercaptan
Low molecular weight mercaptans have a very strong and persisting odor
(skunk). Ethanethiol is used as an odorant in liquid propane gas so that it
can be detected easily by the human nose. These compounds are prepared
by reacting hydrogen sulfide with an alkylsulfate solution and distilling the
final product.
Spectral The S-H absorption is very weak, but is located in a spectral region that is
Interpretation relatively free of interferences (around 2560 cm-1). The methylene wagging
adjacent to the thiol group occurs at around 1250 cm-1. The carbon/sulfur
absorption is weak and may occur in the region 720 - 620 cm-1
The Raman S-H stretch is invariably strong and if this technique is

available it can be used to confirm the identity of this functional group.


Amine Salts
Amine Salts
General section for: Aliphatic Primary Amine Hydrochlorides
Primary Amine Salts
Secondary Amine Salts
Tertiary Amine Salts
Spectral The salts of amines are quite different spectroscopically as compared to the
Interpretation non-salt forms. In the first example the spectrum of propylamine and
propylamine hydrochloride are presented. A primary amine typically shows
the –NH2 split absorption as shown in the top spectrum. When the salt is
formed the –NH2 stretching absorption shifts to around 3000 cm-1 . In
addition the –NH2 wag of the free amine essentially disappears in the salt-
form spectrum.

Aromatic Acid Halides
Aromatic Acid Halides

General section for: Benzoyl Chlorides
Chemical Properties Acid chlorides are prepared from the corresponding acids by reaction with
thionyl chloride, phosphorus trichloride, or potassium pentachloride.
Because of their reactivity in nucleophilic substitution, acid chlorides are
commonly used as intermediates in the synthesis of many organic
compounds.

Aromatic Anhydrides
Aromatic Anhydrides
Chemical Properties
Spectral All anhydrides show two carbonyl absorption bands. The frequency and
Interpretation relative intensities of these two bands depends on whether or not the
carbonyls are conjugated and if the compound is cyclic in nature. Typically
for linear anhydrides the bands are at approximately 1810 and 1755 cm-1.
With five member cyclic structures the ring strain causes the frequencies to
shift about 1860 and 1775 cm-1.
The fact that two carbonyls are seen is a result of the coplanar CO-O-CO
structure which gives rise to symmetric and asymmetric carbonyl vibrations.

Aromatic Benzaldehydes
Aromatic Benzaldehydes
General section for: Benzaldehydes
Chemical Properties The most common of the aromatic aldehydes is benzaldehyde. It is a

colorless, volatile oil with an odor resembling bitter almonds. The density
is 1.0415 with a boiling point of 178 degrees Centigrade. It is derived by
the air oxidation of toluene with uranium or molybdenum oxide catalysts.
This compound is important as an intermediate in the synthesis of dyes,
flavorings, and perfumes.
Spectral Aromatic rings in conjugation with the aldehyde carbonyl have only a
Interpretation minor effect on the -C=O stretching absorption. For example, the carbonyl
absorption for benzaldehyde is at 1705 cm-1.
The two characteristic CH stretching absorptions that are seen for aliphatic
aldehydes are also present in the aromatic compounds. This doubling is
due to Fermi resonance between the -CH stretching absorption and the
first overtone of the -CH deformation.

Aromatic Benzamides
Aromatic Benzamides
General section for: Anilines, Primary
Chemical Properties
Spectral NH stretching
Interpretation
Primary Near 3350 - 3180 cm-1
3320 - 3070 cm-1(trans and

Secondary
cis)
CO (amide I)
Primary Near 1650 cm-1
Tertiary 1670 - 1630 cm-1

Aromatic Benzamides
NH2 def. (amide II)

Primary 1650 - 1620 cm-1
Amide III
Secondary Near 1270 cm-1

Aromatic Esters
Aromatic Esters
General section for: Aromatic Benzoate Esters
Aromatic Esters
Phenyl Acetate Esters
Chemical Properties
Spectral The expected lowering of the carbonyl frequency when conjugated with an
Interpretation aromatic ring causes the aliphatic 1745 cm-1 carbonyl absorption to be
shifted to about 1730-1720 cm-1.
In contrast, when the structure of the ketone is CO-O-C=C the carbonyl

absorption is shifted to higher frequencies. This absorption is generally
found around 1775 cm-1 as is the case for the spectrum of phenyl acetate.
Ester Absorptions C=O Stretch
Saturated 1750 - 1730 cm-1
Unsaturated 1730 - 1715 cm-1
Vinyl 1775 - 1755 cm-1
Alpha keto 1755 - 1740 cm-1

Aromatic Esters
C-O Stretch
Formate 1200 - 1180 cm-1
Acetate 1250 - 1230 cm-1
Phenolic acetates 1250 - 1230 cm-1
Acrylates 1300 - 1200 cm-1

Aromatic Ethers
Aromatic Ethers
General section for: Anisoles (Methoxybenzenes)
Chemical Properties
Spectral The -C-O-C- stretching absorption is found in the 1270-1230 cm-1 range
Interpretation for aryl ethers. In comparing the ortho, meta, and para isomers, the meta
forms are found at a slightly higher frequency (+5 cm-1).
Alkyl ethers 1150 - 1060 cm-1 (strong)
Aryl ethers 1270 - 1230 cm-1 (strong)
Cyclic ethers Near 1250 cm-1 (strong)
Alkyl peroxides 890 - 820 cm-1 (variable)

Aromatic Halide Carboxylic Acid Salts
Aromatic Halide Carboxylic Acid Salts

Spectral When ionization of the acid occurs giving rise to the R-COO (-minus)
Interpretation group, resonance is possible between the two -CO groups. As a result, the
characteristic acid group absorption around 1700 cm-1 disappears and is
replaced by two bands; the first occurring between 1615 and 1550 cm-1
and the second in the 1400 - 1300 cm-1 region. These absorptions
correspond to the asymmetric and symmetric vibrations of the R-COO (-
minus) group. Of these two bands, the band around 1600 cm-1 is most
indicative since the symmetric absorption occurs in the crowded fingerprint
region.

Aromatic Hydrocarbons
General section for: Alkyl Benzenes
Deuterated Aromatics
1,2-Dialkyl Benzenes
Meta Substituted Aromatic Hydrocarbons
Mono-Alkyl Benzenes
Mono Substituted Aromatic Hydrocarbons
Ortho Substituted Aromatic Hydrocarbons
Para Substituted Aromatic Hydrocarbons
For simplicity the vibrational modes of aromatic compounds are usually

considered to consist of separate C-H and or ring C=C vibrations. While
this works as a first order approximation in reality "complex” molecular
interactions occur resulting in the actual measured spectrum.
Chemical Properties In 1858 August Kekule proposed that carbons can combine to form chains
and that these chains can be closed to form rings.
Nomenclature:
The position of aromatic hydrogen atoms on substituted aromatic rings

gives rise to a characteristic pattern of out-of-plane deformation vibrations
in the region between 2000 and 1700 cm-1 as shown below.

Spectral
Interpretation
These bands are weak and may be interfered with by olefin and carbon-
oxygen double bonds.


Aromatic Mercaptans
Aromatic Mercaptans
Spectral The S-H absorption is very weak but is located in a spectral region that is
Interpretation relatively free of interference (around 2560 cm-1). The methylene wagging
adjacent to the thiol group occurs at around 1250 cm-1. The carbon/sulfur
absorption is weak and may occur in the region 720 - 620 cm-1.
The Raman S-H stretch is invariably strong and if this technique is

available it can be used to confirm the identity of this functional group.

Aromatic Nitriles
Aromatic Nitriles
General section for: Aromatic Isocyanates
Aromatic Isocyanides
Aromatic Isothiocyanates
Aromatic Nitriles
Aryl Isocyanates
Aryl Isothiocyanates
Benzonitriles
Chemical Properties
Spectral The infrared absorption due to nitrile groups are, as would be expected,
Interpretation found in the triple bond region of 2300-2000 cm-1. In the case of saturated
alkyl nitriles the band occurs between 2260 and 2240 cm-1. For isocyanates
the absorption is in the 2275-2240 cm-1 region.
The C=N stretching absorption for open chain compounds occurs in the
1690-1590 cm-1 region. The alpha/beta unsaturated compounds absorb
between 1660 and 1590 cm-1 and the conjugated cyclic compounds absorb

Aromatic Nitriles

Aromatic Nitro Compounds
Aromatic Nitro Compounds

General section for: Nitrobenzenes
Chemical Properties
Spectral When a nitroso compound has an amino group in the ortho or para
Interpretation position there are usually strong absorptions around 1330 and 1110 cm-1.
When a hydroxyl group is situated in the ortho or para position, a

tautomeric form exists. Absorptions are then found at 1640 and 1615 cm-1.

Aromatic Phenones
Aromatic Phenones
Chemical Properties
Spectral Ketones show a strong absorption in the region from 1725-1660 cm-1. This
Interpretation band, usually the most intense in the spectrum, is due to C=O stretching
vibration. The following table gives typical ranges.
Saturated open chain ketones 1725 - 1705 cm-1
Alpha - beta unsaturated 1690 - 1675 cm-1
Aryl ketones 1690 - 1660 cm-1
Diaryl ketones 1670 - 1660 cm-1
Halogen atoms in the alpha position often give rise to a higher frequency
shift (i.e., 1715 to 1735 for one halogen and 1760 cm-1 for two halogens.)
In vapor phase alkyl ketone spectra the carbonyl is shifted 10-15 cm-1
toward higher frequencies.
There is only a small low frequency shift for the carbonyl stretching
absorption in aryl ketones. For example, acetophenone shows the -C=O
stretch at around 1692 cm-1 (most other aryl ketones absorb in the 1690-
1680 cm-1 regions). In benzophenones the added conjugation causes this
absorption to appear at 1660 cm-1.
In ketone compounds, where there is an alpha halogen, about a 20 cm-1

shift to higher frequencies is usually seen. This effect increases with
multiple halogen substitutions.

Aromatic Phenones

Aromatic SO Compounds
General section for: Aromatic Halide Sulfonic Acid Salts
Aromatic Sulfonates
Aromatic Sulfones
Aromatic Sulfonic Acids
Aromatic Sulfoxides
Chemical Properties
Spectral Sulfur-Oxygen Assignments

Interpretation
C-SO-C 1070-1035 cm-1 (s)
O-SO-O Near 1225 cm-1 (s)
N-SO-N Near 1120 cm-1 (s)
S-SO-S Near 1105 cm-1 (s)
C-SO2-C 1330-1305 cm-1 (s)
C-SO2-NR2 1360-1335 cm-1 (s)
1170-1150 cm-1 (s)
C-SO2-OR 1380-1350 cm-1 (s)
1190-1180 cm-1 (s)
R-OSO2-OR2 1415-1380 cm-1 (s)
1190-1175 cm-1 (s)

R-SO3-Na 1190-1175 cm-1 (s)

1065-1060 cm-1 (s)

Benzoic Carboxylic Acids
Benzoic Carboxylic Acids

General section for: Benzoic Acids
Chemical Properties Carboxylic acids show very high boiling points relative to the
corresponding normal alkanes and are even higher than the alcohols. This
is due to the fact that a pair of acid molecules (a dimer) are held together
by two hydrogen bonds.
The carboxylic acids are named as derivatives of the parent acid.
CH3CH2CH2CH2COOH Pentanoic acid

Carboxylic Acids
Carboxylic Acids
General section for: Aliphatic Acrylic Acids
Aliphatic Carboxylic Acids
Phenyl Carboxylic Acids
Chemical Properties Carboxylic acids show very high boiling points relative to the
corresponding normal alkanes and are even higher than the alcohols. This
is due to the fact that a pair of acid molecules (a dimer) are held together
by two hydrogen bonds.
The carboxylic acids are named as derivatives of the parent acid.
CH3CH2CH2CH2COOH Pentanoic acid
Spectral Carboxylic acids normally exist in a dimeric form with very strong
Interpretation hydrogen bonds between the carbonyl and hydroxyl groups. This
association results in the very broad, unusual -OH stretching absorption
which occurs from about 3100 to 2200 cm-1. A number of other
absorptions are also very indicative of the acid group.
C=O stretching 1725-1700 cm-1
C-O stretching 1440-1395 cm-1
& 1320-1210 cm-1
OH deformation 950-900 cm-1

Carboxylic Acids

Carboxylic Acid Salts

General section for: Aliphatic Ammonium Carboxylic Acid Salts
Aliphatic Carboxylic Acid Salts
Benzoic Acid Salts
Carboxylic acid salts typically show a strong, characteristic asymmetric

stretching absorption from the CO2- group in the 1650-1550 cm-1 region.
The corresponding symmetric stretching absorption occurs at around
1440-1335 cm-1. For acid salts with a strongly electronegative group the
asymmetric stretching absorption will shift to higher frequencies (around
1690 cm-1). Fairly strong rocking in and out of plane deformation
absorptions are observed in the 770-400 cm-1 region.
Chemical Properties Although they are much weaker acids than the strong mineral acids
(sulfuric, hydrochloric, nitric), the carboxylic acids are tremendously more
acidic than the very weak organic acids (alcohols, acetylene). As a result, the
aliphatic carboxylic acids readily form the carboxylate ion in aqueous
solutions. A water soluble organic compound that dissolves in cold, dilute
aqueous sodium hydroxide is almost always a carboxylic acid. This provides
a mechanism for separating an acid from a mixture. The acid will dissolve
in the basic aqueous solution and then may be converted back to the acid
by acidification of the solution.
Spectral When ionization of the acid occurs, giving rise to the R-COO- group,
Interpretation resonance is possible between the two -CO groups. As a result, the
characteristic acid group absorption around 1700 cm-1 disappears and is
replaced by two bands; the first occurring between 1615-1550 cm-1 and the
second in the 1400-1300 cm-1 region. These absorptions correspond to the
asymmetric and symmetric vibrations of the R-COO- group. Of these two
bands, the band around 1600 cm-1 is most indicative since the symmetric
absorption occurs in the crowded fingerprint region.


Halides
Halides
General section for: Aliphatic Bromides
Aliphatic Chlorides
Aromatic Chlorine
Aromatic Fluorine
Brominated Linear Alkanes
Chlorinated Linear Alkanes
Fluorinated Linear Alkanes
Chemical Properties The alkyl halides have the general formula R-X where R is an alkyl group.
The nomenclature of the alkyl halides is based on the parent alkyl group.
HOCH2CH2CH2Br 3-Bromopropanol
The halide group produces a molecule with a higher molecular weight than
the corresponding simple alkane and as a result the haloalkanes have much
higher boiling points as compared with alkanes of the same number of
carbons.
Industrial production of alkyl halides is by the addition of the halogen

atom to an unsaturated carbon/carbon bond.
Spectral The only characteristic absorptions shown by halogen compounds in the mid
Interpretation infrared spectrum arise from the C-X stretching absorptions. Unlike aliphatic
compounds, there does not appear to be unique positions for the halogen
stretching absorptions when attached to an aromatic ring. This type of
vibration is sensitive to frequency shifts caused by variations in the
neighboring groups (this is most significant for the lighter halides such as -F).
-C-F (1400-1000 cm-1)
-C-Cl (1400-1000 cm-1)
-C-Br (1400-1000 cm-1)
-C-I (1400-1000 cm-1)

Halides

Heterocyclics
Heterocyclics
General section for: Furans
Pyroles
Spectral
Interpretation
Pyridines and Quinolines
3090 - 3060 and 3050 - 3010

CH stretching
cm-1
1615 - 1585 (all medium), 1588

Ring breathing
- 1560,
1520 - 1510, 1438 - 1410 cm-1
CH deformation 2 - subst. 790 - 740 cm-1
3 - subst. 825 - 770 cm-1
4 - subst. 845 - 790 cm-1

Heterocyclics
Five Member Fused Heterocyclic
3250 - 3050 cm-1 (1 to 3

CH stretch
bands)
Ring breathing
1600 - 1400 (multiple)
bands
CH deformations 900 - 700 (strong and vary)
Five membered heteroaromatic ring compounds such as pyrroles, furans,

and thiophenes generally show bands related to the C=C in-plane
vibrations around 1580cm-1, 1490 cm-1, and 1400cm-1. For those structures
that have CH=CH groups there is a strong band in the 800-700 cm-1
region due to an out-of-plane deformation vibrational mode.
Furan compounds show bands due to the =C-H stretching vibration just
above 3000 cm-1. Substituted furans have strong to medium bands at 1618-
1560 cm-1, 1520-1470 cm-1 and 1400-1390 cm-1 which are due to the C=C
ring stretching modes.
Pyrrole compounds show bands due to the =C-H stretching vibration

around 3100 cm-1. Pyrroles have one or two bands between 1600 cm-1 and
1550 cm-1 depending on whether or not the nitrogen hydrogen is present
or absent. A strong band around 1400 cm-1 is generally observed.

Inorganic Carbonate
Inorganic Carbonate
General section for: Inorganic Carbonates/Bicarbonates
Spectral The infrared absorption spectra of inorganic carbonate compounds are very
Interpretation distinctive. The strong, characteristic absorptions are found around
1420cm-1, 850cm-1 and 700cm-1. The two lower frequency bands are very
sharp. All of the band positions are somewhat dependent on the hydration
state of the sample. The example spectra were run as nujol mulls and the
strong carbon hydrogen stretching absorption around 2900 -1 has been
blanked to prevent confusion.

Inorganic Nitrates
Inorganic Nitrates
Spectral Inorganic nitrates have very characteristic spectra. There are three
Interpretation characteristic bands at around 1780 cm-1, 1380 cm-1 and 830 cm-1. The
1380 cm-1 band is the strongest and is relatively broad while the other two
absorptions are weaker and very narrow. There may also be the typical
water bands around 3400 cm-1 and 1640 cm-1. The example spectra were
run as nujol mulls. The CH absorptions due to the mulling oil have been
blanked for clarity.

Inorganic Nitrites
Inorganic Nitrites
Spectral Inorganic nitrites have relatively simple infrared spectra. The spectra consist
Interpretation of two bands: a broad, strong band around 1260 cm-1 and a very sharp,
medium intensity band around 825 cm-1.

Inorganic Phosphates
Inorganic Phosphates
Spectral Inorganic phosphates have very characteristic spectra. There are two strong
Interpretation bands at around 1000 cm-1 and 550 cm-1. There are also typically water
bands around 3400 cm-1 and 1640 cm-1. The example spectra were run as
nujol mulls. The CH absorptions due to the mulling oil have been blanked
for clarity.

Inorganic Sulfates
Inorganic Sulfates
Spectral Inorganic sulfates have very characteristic spectra. There are two characteristic
Interpretation bands at around 1125 cm-1 and 630 cm-1. The 1125 cm-1 band is the
strongest and is relatively broad while the other absorption band is weaker
and very narrow. There may also be the typical water bands around 3400 cm-
1
and 1640 cm-1. The example spectra were run as nujol mulls. The CH
absorptions due to the mulling oil have been blanked for clarity.

Kaolin Clays / Alumino Silicates
Kaolin Clays / Alumino Silicates

Spectral Inorganic silicates, alumino silicates, and clay type materials have very
Interpretation characteristic spectra. There is a characteristic strong band centered around
1100 cm-1 which sometimes appears as one band and in other samples as
multiple bands (see example spectra). There may also be bands due to
associated water molecules around 3400 cm-1 and 1640 cm-1. The waters in
the clay lattice often give rise to sharp bands as shown in one of the
example spectra.

Mono Substituted Anilines
Mono Substituted Anilines

Spectral The aromatic anilines exhibit amine bands which are similar to that of the
Interpretation aliphatic amine functional groups. If two hydrogens are present on the
nitrogen atom a three band pattern is found in the -NH stretching region
around 3400 cm-1. If there is one hydrogen on the nitrogen atom a single
band is found in this region. The aniline C-N stretching bands occur in the
region around 1300-1100 cm-1 but are generally weak and not very useful
in a diagnostic sense.

Olefins
Olefins
General section for: Cis-Alkenes
Cis Olefins
Internal Aliphatic Olefins
Olefins (general)
Polybutadienes
Terminal Aliphatic Olefins
Terminal Vinyl Olefins
Trans-Alkenes
Trans Olefins
Chemical Properties Olefins consist of at least one double bond between adjacent carbon atoms.
There is hindered rotation about any carbon-carbon double bond which
can result in geometric isomers.
HOCH2CH=CH2 3-propenal
Spectral Carbon-Carbon Stretching Vibrations

Interpretation
Non-conjugated 1680 - 1620 cm-1 (intensity varies)
Around 1625 cm-1 (enhanced

Phenyl conjugated
intensity)
C=O;C=C Around 1600 cm-1 (enhanced

conjugated intensity)

Olefins
Carbon-Hydrogen Stretching and Deformation Vibrations
-CH=CH- (trans) 3040-3010cm-1 (m) CH str.
-CH=CH- (trans) 970-960cm-1 (s) CH def.
-CH=CH- (trans) 1310-1295cm-1 (s-w) CH def.
-CH=CH- (cis) 3040-3010cm-1 (m) CH str.
-CH=CH- (cis) circa 690cm-1 (w) CH def.
-CH=CH2 (vinyl) 3040-3010cm-1 (m) CH def.
-CH=CH2 (vinyl) 3095-3075cm-1 (m) CH str.
-CH=CH2 (vinyl) 995-985cm-1 (s) CH def.
-CH=CH2 (vinyl) 915-890cm-1 (s) CH def.
-CH=CH2 (vinyl) 1855-1800cm-1 (m) Overtone

Olefins

Perfluorinated Alkanes
Perfluorinated Alkanes
Spectral Aliphatic hydrocarbons where all of the hydrogens have been replaced by
Interpretation fluorine atoms are known as perfluorinated. These compounds are fairly
common and give rise to a fairly simple spectrum showing a split -C-F
stretching absorption centered around 1200 cm-1. In the example spectrum
the sample was run as a nujol mull and the nujol oil bands have been
blanked for clarity

Silicon Organics
Silicon Organics
General section for: Alkoxyalkylsilanes
Hydro Siloxanes
Hydrosilanes
Silicone Oils and Greases
Substituted Silanes
Trialkylsilanes
Spectral The infrared absorption spectra of silicon organic compounds are very
Interpretation distinctive. The Si-H absorptions occurs around 2100 cm-1. This band is
generally strong in intensity and somewhat broad in nature. The Si-H
deformation occurs in the 900-800 cm-1 region.
Silicon organic compounds with a methyl group attached to the silicon

atom are very common. Methyl groups attached to a silicon atom give rise
to a characteristic sharp symmetrical deformation absorption around 1260
cm-1. The asymmetrical deformation is weaker and occurs around 1400
cm-1.
Other common silicon organic compounds are those containing the Si-O-
C or Si-O-Si groups. The Si-O-Si stretching absorption is around 1050
cm-1. This is generally a fairly strong band. The Si-O-C absorption is
around 100 cm-1 lower and weaker in intensity.

Silicon Organics

Trifluoromethane Sulfonates
Trifluoromethane Sulfonates
Spectral The infrared absorption spectra of trifluoromethane sulfonate compounds
Interpretation are very distinctive. The strong, characteristic absorptions are found around
1420cm-1, 1200cm-1 and 900cm-1. All of the bands may show splitting.

IR Spectral Interpretation

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IR Spectral Interpretation

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Aliphatic Acid Halides ....................................................................................... 4

Aliphatic Alkynes ................................................................................................ 7

Aliphatic Amides ................................................................................................. 9

Aliphatic Amines ............................................................................................... 11

Aliphatic Amino Acids...................................................................................... 13

Aliphatic Anhydrides ........................................................................................ 15

Aliphatic Hydrocarbons ................................................................................... 19

Aliphatic Ketones .............................................................................................. 22

Aliphatic Nitriles ............................................................................................... 24

Aliphatic Nitro Compounds ............................................................................. 26

Aliphatic Phosphorous Compounds............................................................... 27

Aliphatic SO Compounds ................................................................................. 30

Aliphatic Thiols/Mercaptans .......................................................................... 32

Aromatic Acid Halides ..................................................................................... 35

Aromatic Benzaldehydes ................................................................................. 37

Thermo Scientific Infrared Spectral Interpretation i

Aromatic Ethers ..................................................................................................42

Aromatic Halide Carboxylic Acid Salts.........................................................43

Aromatic Hydrocarbons ....................................................................................44

Aromatic Nitro Compounds..............................................................................50

Aromatic SO Compounds ..................................................................................53

Benzoic Carboxylic Acids ................................................................................55

Carboxylic Acids ................................................................................................56

Carboxylic Acid Salts........................................................................................58

Inorganic Carbonate ..........................................................................................64

Inorganic Nitrates ..............................................................................................65

Inorganic Nitrites ...............................................................................................66

Kaolin Clays / Alumino Silicates.....................................................................69

Mono Substituted Anilines...............................................................................70

Perfluorinated Alkanes .....................................................................................74

Trifluoromethane Sulfonates ...........................................................................77

ii Infrared Spectral Interpretation Thermo Scientific

Thermo Scientific Infrared Spectral Interpretation 1

-C-O stretching and -OH deformation vibrations

Primary alcohols 1050 cm-1

Secondary alcohols 1100 cm-1

Tertiary alcohols 1150 cm-1

Phenols 1200 cm-1

2 Infrared Spectral Interpretation Thermo Scientific

-OH stretching frequencies Free -OH form

Primary alcohols 3643 - 3630 cm-1

Secondary alcohols 3635 - 3620 cm-1

Tertiary alcohols 3620 - 3600 cm-1

Phenols 3612 - 3593 cm-1

Thermo Scientific Infrared Spectral Interpretation 3

Aliphatic Acid Halides

Spectral The attachment of a halide to a carbonyl carbon atom results in a shift of

4 Infrared Spectral Interpretation Thermo Scientific

Thermo Scientific Infrared Spectral Interpretation 5

6 Infrared Spectral Interpretation Thermo Scientific

H:C:::C:H m.p. -82 / b.p. -75

The IUPAC naming is based on the closest triply bonded carbon.

CH3-C:::C-CH(CH3)2 chain = Five carbons; 4-Methyl-2-pentyne

Acetylene is the family member of chief industrial importance and is

Thermo Scientific Infrared Spectral Interpretation 7

1-octyne is asymmetric with a hydrogen on the triply bonded carbon.

8 Infrared Spectral Interpretation Thermo Scientific

3320 - 3070 cm-1(trans and

Primary Near 1650 cm-1

Secondary 1680 - 1630 cm-1