1

pKa Values
INDEX
Inorganic

Imidazole

27

Phosphates

3-4

Phenazine

27-28

Carboxylic acids

4-9

Pyridines

28-29

Phenols

Pyrazines

30

Alcohols and oxygen acids

9-13

Quinoline

31

Amino Acids

13-14

Quinazoline

31

Peptides

14-15

Quinoxaline

31-32

Nitrogen Compounds

15

Special Nitrogen Compounds

32

Aliphatic amines

15-19

Hydroxylamines

32

Cyanoamines

17

Hydrazines

32

Anilines

20-22

Semicarbazones

32

Nucleosides

24

Amidoximes

32

Special Table Heterocycles

25

Thiols

33

Acridine

26

Carbon Acids

33-35

Benzoquinoline

26

Indicators

35

Hydantoin

27

References

36-37

Cinnoline

23

For complex chelating agents, see also reference 77.

Note. This document was compiled by W.P. Jencks and has been added to by F.H. Westheimer

ACIDS
Compound
AgOH
Al(OH)3
As(OH)3
H3 AsO4
H2 AsO4
HAsO4*
As2 O3
H3 AsO3
H3 BO3
H2 B4 O7
HB4 O7
Be(OH)2
HBr
HOBr
HOCl
HClO2
HClO3
HClO4 (70%)
CH3SO3H
HCN
H2CO3
HCO3
H2CrO4
HCrO4
HOCN
HZ
H2 GeO3
Ge(OH)4
HI
HOI
HIO3
H4IO6
H5IO6
HMnO4
NH3 OH*
NH4*
HN3
HNO2
HNO3
N2 H5+
H2 N2 O2
H2 N2 O2
H2 OsO5
H2 O
H3 O+

Compound
pK

Ref.

3.96
11.2

4
28

9.22

28

2.22, 7.0, 13.0

6.98*
11.53*
0
9.22*
9.23*
4.00
9.00
3.7
-9.00
8.7
7.53, 7.46
2.0
-1.00
-10.00
-0.6
9.40
6.37, 6.35*, 3.58
10.33*
-0.98
6.50*
3.92
3.17*, 0.59*
8.59, 12.72
8.68, 12.7
-10.0
11.0
0.8
6.00
1.64, 1.55, 8.27
-2.25
5.98*
9.24*
4.72*
3.29
-1.3
7.99*
7.05
11.0
12.1
15.7
-1.7

28
77
77
4
28
34
34
4
31
28
28, 33
28
28
31
31
34
34, 32
30
2, 30
34
77
34, 78
28
31
28
28
34
34, 28
30
77
77
28
28
77
34
34
34
none
none

Pb(OH)2
H3 PO2
H2 PO4
HPO4_
H3 PO3
H2 PO3
H4 P2O7
H3 P2 O7
H2 P2O7 =
HP2 O7=
HReO4
HSCN
H2SeO3
HSeO3
H2SeO4
HSeO4
H3SiO3
H2SO3
H2SO4
HSO3
HSO4
H2S2 O4
H2Se
HSe
H2S
HS
HSbO2
HTe
H2Te
H2TeO3
Te(OH)6
H2 VO4
HVO4 =
H2CrO4
HOCN
HSCN
H3 PO2
H3 PO4
H2S2 O3
H3 AuO3
H3 GaO3
H5IO6

pK

6.48 (10.92)
2.0, 2.23*
7.21*
12.32*
2.0
6.58*
1.52*
2.36*
6.60*
9.25*
-1.25
4.00
2.6, 8.3, 2.62*
8.32
Strong, 2.0
2.00
10.0
1.9, 7.0, 1.76*
-3.0, 1.9
7.21*
1.99*
1.9
3.89*
11.00*
7.00*
12.92*
11.0
5.00
2.64, 11.0
2.7, 8.0
6.2, 8.8
8.95
14.4
0.74
3.73
0.85
1.07
2.12*
0.60*, 1.72*
13.3, 16.0
10.32, 11.7
3.29, 6.70, 15.0
(see above!)
H4 V6 O17
1.96
H2 NSO3 H
1.0
* Indicates a thermodynamic value.

Ref.
4 (78)
28
77
77
28
77
77
77
77
77
30
34
28
77
28
34
34
28, 77
28
77
77
29
77
77
77
77
34
34
34, 78
28
28
30
30
77
77
77
77
77
77
78
78
78
78
80

3
PHOSPHATES AND PHOSPHONATES
Phosphates
Compound
Phosphate
Glyceric acid 2-phosphate
Enolpyruvic acid
MethylEthyln-Propyln-ButylDimethylDi-n-propyl
Di-n-butylGlucose-3Glucose-4-glycero-glycero3-phosphoglyceric acid
2-phosphoglyceric acid
peroxymonophosphoric
acid
diphosphoglyceric acid
glyceraldehydedioxyacetonehexose difructose-6glucose-6glucose-1adenylic acid
inosinic acid
ADP
ATP
pyrophosphoric acid
phosphopyruvic acid
creatine phosphate
arginine phosphate
arginine
amino phosphate
trimetaphosphate

pK

Ref.

1.97, 6.82, 12.5

3.6, 7.1
3.5, 6.4
1.54, 6.31
1.60, 6.62
1.88,6.67
1.80, 6.84
1.29
1.59
1.72
0.84, 5.67
0.84, 5.67
1.40, 6.44
1.37, 6.34
1.42, 3.42
1.42, 3.55, 7.1

55
53
53
55
55
55
55
55
55
55
56
56
54
54
54

4.05
7.40, 7.99
2.10, 6.75
1.77,6.45
1.52, 6.31
0.97, 6.11
0.94, 6.11
1.10, 6.13
3.8?, 6.2?
2.4?, 6.4?
2 strong, 6.6
3 strong, 6.6
0.9, 2.0, 6.6, 9.4
3.5, 6.38
2.7, 4.5
2.8, 4.5, 9.6, 11.2
2.02, 9.0, 12.5
(-0.9), 2.8, 8.2
2.05

69
54
54
54
54
54
54
54
54
54
54
54
54
54
54
54
54
54
77

<2, 2.75, 7.54, 8.38

<2, 2.65, 7.34, 8.35
<2, 2.6, 7.00, 9.27
<2, 2.57, 6.87, 10.33
2.35
2.43
2.45
2.55, 7.75

57
57
57
57
57
57
57
57

Phosphonates
H2 O3P(CH2)4 PO3 H2
H2 O3P(CH2)3 PO3 H2
H2 O3PCH2CH(CH3 )PO3 H2
H2 O3PCH2 PO3 H2
MethylEthyln-propylisopropyl-

Compound

pK

n-butylisobutyls-butylt-butylneopentyl-

2.59, 8.19
2.70, 8.43
2.74, 8.48
2.79, 8.88
2.84, 8.65

Ref.
57
57
57
57
57

1,1 Dimethylpropyl2.88, 8.96

n-hexyl2.6, 7.9
n-dodecyl--, 8.25
CH3(CH2)5 CH(COOH)- 1, -CF31.16, 3.93
CCl31.63, 4.81
NH3+CH22.35, 5.9
(OOCCH2)2 NH+CH2 --, 5.57
CHCl2 1.14, 5.61
CH2CI1.40, 6.30
CH2Br1.14, 6.52
(OOCCH22 NH+(CH2)2 - --, 6.54
CH2I1.30, 6.72
NH3+CH2CH22.45, 7.00
C6H5 CH=CH2.00, 7.1
HOCH21.91, 7.15
C6H5 NH2+(CH2 )32.1, -C6H5 NH(CH2)3 --, 7.17
Br(CH2)22.25, 7.3
CH3(CH2)5 CH(COO) --, 7.5
C6H5 CH22.3, 7.55
NH3+(CH2)4)2.55, 7.55
NH3+(CH2)52.6, 7.6
NH3+(CH2)10--, 8.00
OOC(CH2)10--, 8.25
(CH3)3SiCH23.22, 8.70
C6H5 CH23.3, 8.4
(C6 H5)SC3.85, 9.00

57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57
57

Arylphosphonic acids
2X-RC6H3PO3H2
X
R
pK

Ref.

Cl
Br
Cl
Cl
Br
Br
Cl
CH3O
CH3O
CH3O
HO
O2 N

57
57
57
57
57
57
57
57
57
57
57
57

4-O2 N
5-O2 N
5-Cl
H
H
5-CH3
4-NH2
4-O2 N
H
4-O2 N
4-O2 N
H

1.12, 6.14
(a), 6.14
(a), 6.63
1.63, 6.98
1.64, 7.00
1.81, 7.15
--, 7.33
1.53, 6.96
2.16, 7.77
--, 8.22
1.22, 5.39
1.45, 6.74

pK

Ref.

F
H
1.64, 6.80
57
I
H
1.74, 7.06
57
NH2 H
--, 7.29
57
CH3 H
2.10, 7.68
57
C6H5
H
(a), 8.13
57
HOOC
H
1.71, 9.17
57
**These values were obtained in 50% ethanol.
(a) The compounds were not sufficiently soluble.
For graphical plots of a large number of substituted
phosphorus compounds see 83.

4
triphosphate
tetrametaphosphate
fluorophosphate

8.90, 6.26, 2.30

2.74
0.55, 4.8

Phosphonates (Ref. 2)
X
-H

-H

X(CH2 )PO3 H2
2.35
7.1
X(CH2 )2PO3 H2
2.45
7.85
X(CH2 )4PO3 H2
X(CH2 )5PO3 H2
X(CH2 )6PO2 H2
2.6
7.9
X(CH2 )10PO2 H2
Phosphines in acetonitrile, see Ref. 89

77
77
56

Tartaric +
+ or meso
Vinylacetic

-NH3+ -NH3+
1.85
2.45
2.55
2.6

CARBOXYLIC ACIDS
Aliphatic
Compound
pK

5.35
7.00
7.55
7.65
8.00

Ref.

Acetoacetic
3.58
Acetopyruvic
2.61, 7.85 (enol)
Aconitic, trans2.80, 4.46
Betaine
1.84
Citric
3.09, 4.75, 5.41
Crotonic
4.69
Dihydroxyfumaric
1.14
Dethylenediamine2.00, 2.67
tetraacetic
6.16, 10.26
Formic
3.77*
Fumaric
3.03, 4.54
Glyceric
3.55
Glycollic
3.82
Glyoxylic
3.32
Homogentistic
4.40
-keto--methyl valeric 2.3
Lactic
3.86
Maleic
1.93, 6.58
Malic
3.40, 5.2

6
6
6
6
6
6
6
6

Compound

Ref.

pK

2
6
6
6
6
6
6
6
6
6

Oxaloacetic (trans-enol) 2.56

+(cis-enol)
2.15, 4.06
Protocatechuic
4.48
Pyruvic
2.50

6
6
6
6

Compound

Ref.

pK

i-C3 H7S3.72*
C6H5 CH2S3.73*
C2H5S3.74*
n-C3 H7S3.77*
n-C4 H9S3.81*
HO3.83*
O3S4.05
(C6 H5)3CS4.30*
C6H5 4.31*
CH2-CH4.35*
*Indicates thermodynamic values.

20
20
20
20
20
20
20
20
20
20

2.99, 4.40
2.89, 4.40
3.22, 4.85
4.42

6
6
6
6

Acetic acids, substituted

Compound
pK

Ref.

HO2 N(CH3)3 N+(CH3)2 NH+CH3 NH2+NH3+CH3SO2NCC6H5SO2HO2C

C6H5SOFClBrCl2F2Br3Cl3F3HONC4
F3CN3IC6H5 OC2H5 O2 CC6H5SCH3ONCSCH3COC2H5 On-C3 H7 O
n-C4 H9 O
sec.-C4 H9 OHSi-C3 H7 OCH3S-

20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20
20

4.76*
1.68*
1.83*
1.95*
2.16*
2.31*
2.36*
2.43*
2.44
2.83*
2.66
2.66
2.86*
2.86
1.29
1.24
0.66
0.65
0.23 (-0.26) (2)
3.01
3.07*
3.03
3.12
3.12
3.35
3.52*
3.53
3.58
3.58*
3.60
3.65
3.66
3.67
3.67*
3.69*
3.72*

5
Unsaturated acids (25)
Compound

pK

Ref.

trans-CH3-CH=CHCO2 H
cis-CH3-CH=CHCO2 H
C6H5 -CH2CH2 CO2 H
trans-C6 H5-CH=CHCO2 H
m-CH3 OC6 H4CH2CH2 CO2
m-CH3 OC6 H4CH=CHCO2 H
m-ClC6 H4CH2 CH2CO2 H
H-CH2CH2 CO2 H
H-CH=CHCO2 H
C6H5 CH2CH2 CO2 H
C6H5 CH=CHCO2 H**
C6H5 CH2CH2 CO2 H
C6H5 CH=CHCO2 H**
m-ClC6 H4CH=CHCO2 H**

4.69*
4.44*
4.66*
4.44*
4.65*
4.38*
4.58*
4.88*
4.25*
4.66*
4.44*
4.66*
4.44
4.29*

20
2
2
2
2
2
2
2
2
2
2
2
2
2

Unsaturated acids, Cis- and TransCis-Acid

H

R2

Trans-Acid
R1
R2
C C

C C
R1

C O2H

C O2H

R1

R2

cis-acid

trans-acid

Ref.

HCH3ClC6H5 ClC6 H4
6-BrC6 H4
CH3C6H5 2,4,6-(CH3)3C6 H2C6H5 -

HHHHHHCH3HHCH3-

4.25*
4.44*
3.32
3.88*
3.91
4.02
4.30
5.26***
6.12***
4.98***

4.25*
4.69*
3.65
4.44*
4.41
4.41
5.02
5.58***
5.70***
5.98***

2
2
2
2
2
2
2
2
2
2

Dicarboxylic acids, unsaturated*

Compound
pK
Maleic
1.92, 6.23
Citraconic (Dimethylmaleic
acid)
2.29, 6.15
Acetylenedicarboxylic
1.73, 4.40
1-tetrahydrophthalic
3.01, 5.34
Bromomaleic
1.45, 4.62
Bromofumaric
1.46, 3.57
Chlorofumaric
1.78, 3.81
Fumaric
3.02, 4.38
Mesaconic (Dimethylfumaric
acid)
3.09, 4.75
Phthalic
2.95, 5.41
Itaconic (1-Propene-2-3dicarboxylic acid)
3.85, 5.45
Chloromaleic
1.72, 3.86

Alicyclic Dicarboxylic acids

Compound
Ref.
2
2
2
2
2
2
2
2
2
2
2
2

pK

Ref.

cis-Caronic(1,1-dimethylcyclopropane23-dicarboxylic acid
2.34*, 8.31*
1,2-trans-cyclopropanedicarboxylic
3.65*, 5.13*
trans-caronic
3.82*, 5.32*
1,2-cis-cyclopropanedicarboxylic
3.33*, 6.47*
**trans
***in 40% acetone
*thermodynamic

Aliphatic
Alicyclic Dicarboxylic acids
Compound
pK
1,2-trans-Cyclopropanedicarboxylic
trans-Ethyleneoxide
dicarboxylic

2
2
2
2

Ref

3.65, 5.13

1.93, 3.25

6
1,3-trans -Cyclobutanedicarboxylic
1,2-trans-Cyyclopentanedicarboxylic
1,3-trans-Cyclopentanedicarboxylic
1,2-trans-Cyclohexanedicarboxylic
1,3-trans-Cyclohexanedicarboxylic
1,4-trans-Cyclohexanedicarboxylic

Compound
cis-Ethyleneoxidedicarboxylic
1,3-cis-Cyclobutanedicarboxylic
1,2-cis-Cyclopentanedicarboxylic
1,3-cis-Cyclopentane
dicarboxylic
1,2-cisCyclohexanedicarboxylic
1,3 -cis-Cyclohexanedicarboxylic
1,4-cis-Cyclohexane
dicarboxylic

Dicarboxylic acids*
Compound
oxalic
Malonic
MethylEthyln-propyl
i-propylDimethylMethylethylDiethylEthyl-n-propylDi-n-propylGlutaric
B-Methyl
B-Ethyl
B-n-Propyl
B,B-DimethylB,B-MethylethylB,B-DiethylB,B-Di-n-propyl
D-Tartaric
DL-Tartaric
meso-Tartaric
Succinic
O-O-Dimethyl(high melting)
O-O-Dimethyl-

3.81, 5.28

3.89, 5.91

4.40, 5.45

(low melting)
O,O-Diethyl(high melting)
O,O-Diethyl(low melting)
Tetramethyl-

4.18, 5.93

Compound

pK

Ref.

Adipic
Pimelic
Suberic
Azelaic
DL-1:2-Dichlorosuccinic
meso-1:2-Dichlorosuccinic
DL-1:2-Dibromosuccinic
meso-1:2-Dibromosuccinic
DL-1:2-Dimethylsuccinic
meso-1:2-Dimethylsuccinic
*All are thermodynamic values

4.42, 5.41
4.48, 5.42
4.52, 5.40
4.55, 5.41
1.68, 3.18
1.74, 3.24
1.48, ---1.42, 2.97
3.93, 6.00
3.77, 5.36

2
2
2
2
20
20
20
20
20
20

4.31, 5.73

4.18, 5.42

pK

Ref.

1.94, 3.92

4.03, 5.31

4.37, 6.51

4.23, 5.53

4.34, 6.76

4.10, 5.46

4.44, 5.79

pK

Ref.

1.23, 4.19
2.83, 5.69
3.05, 5.76
2.99, 5.83
3.00, 5.84
2.94, 5.88
3.17, 6.06
2.86, 6.41
2.21, 7.29
2.15, 7.43
2.07, 7.51
4.34, 5.42
4.25, 6.22
4.29, 6.33
4.31, 6.39
3.70, 6.29
3.62, 6.70
3.62, 7.12
3.69, 7.31
3.03, 4.45
3.03, ---3.29, 4.92
4.19, 5.48
3.77, 5.94

2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
2
20
2
2

3.94, 6.20

3.63, 6.46

3.51, 6.60

3.50, 7.28

Aliphatic
Bicyclo[2.2.2]octane-1-carboxylic acids,
4-substituted
Compound
pK
Ref.
HC2H5 O2 CNCHOBr-

6.75
6.31
5.90
6.33
6.08

2
2
2
2
2

Lysergic acid, etc.

Compound

pK

Ref.

ergometrine
Dihydroergometrine
-dihydrolysergol
Lysergic acid
-dihydrolysergic
ergometrinine
-dihydrolysergol
6-methylergoline
isolysergic acid
-dihydrolysergic

6.8, -7.4, -8.2, -7.8, 3.3

8.3, 3.6
7.3, -8.3, -8.85, -8.4, 3.4
8.6, 3.6

2
2
2
2
2
2
2
2
2
2

Hydroxycyclohexanecarboxylic acids
Compound
pk
Ref.
Cyclohexanecarboxylic
cis-1,2
cis-1,3
cis-1,4
trans-1,2
trans-1,3
trans-1,4

4.90
4.80
4.60
4.84
4.68
4.82
4.68

2
2
2
2
2
2
2

Aromatic
Compound

pK

Ref.

benzene-CO3 H

4.20*

7
Anthracene-1-COOH

3.69

Anthracene-9-COOH
naphthalene-2-COOH
Naphthalene-1-COOH

3.65
4.17
3.69

2
2
2

Compound

pK

NC3.60*
HO2C*
2.95*
3.54
F3C3.79
HO2.98*
4.08*
I2.85*
3.86*
Cl2.94*
3.83*
(CH3)3Si4.24*
C2H5 O4.21*
4.17*
i-C3 H7 O4.24*
4.15*
n-C5 H11 OC6H5 3.46*
CH3CH23.77
(CH3)3C3.46
4.28
HO P3.78
4.03
3
O S4.15
3
H2 N4.98
4.79
(CH3)2 N8.42
5.10
HO As3
O C5.41**
4.60
2
CH3 NH5.3
5.10
*thermodynamic
For complex chelating agents, see also Ref. 84
See also page 9a for more carboxylic acids.

Ref.

Substituted benzoic acids (Ref. 2)

COOH

Benzoic acid

HO2 NCH3COCH3SO2CH3SHSBrFCH3On-C3 H7 On-C4 H9 OC6H5 OCH3(CH3)2CH(CH3)3 N+-

4.20*
2.17*

4.21*
3.45*

3.44

3.64*

3.52*

3.53*
3.91*

3.81*
3.87*
4.09*
4.20*
4.25*
3.95*
4.24*

1.37

3.45

4.00*
4.14*
4.47*
4.46*
4.53*
4.52*
4.34*
4.35*
3.43

2.85*
3.27*
4.09*
4.24*

Ortho-substituted benzoic acids

Benzoic acid
pK

Ref.

2-CH32-t-C4 H92,6-(CH3 )22,3,4,6-(CH3)42,3,5,6-(CH3)42-C2 H52-C6 H52,4,6-(CH3)32,3,4,5-(CH3)4-

2
2
2
2
2
2
2
2
2

3.91**
3.46
3.21
4.00
3.52
3.77
3.46**
3.43
4.22

Benzene Polycarboxylic acids

Ref. 2
Acid
Position of carboxyl pKI
Benzoic
Phthalic
Isophthalic
Terephthalic
Hemimellitic
Trimellitic
Trimesic
Mellophanic
Prehnitic
Pyromellitic
Benzenepentacarboxylic
Mellitic
*ionic strength 0.03
**thermodynamic

1
1,2
1,3
1,4
1,2,3
1,2,4
1,3,5
1,2,3,4
1,2,3,5
1,2,4,5
1,2,3,4,5
1.2,3,4,5,6

Carboxylic Acids
Acid

Ref. 77
pK

4.17*
2.98*
3.46*
3.51*
2.80*
2.52*
3.12*
2.06*
2.38*
1.92*
1.80*
1.40*

3.55*
3.51
4.58*
3.99*
4.27*
4.45*
4.68*
4.55*
4.35*
4.40*
3.95
4.11
4.92
5.03
4.22
4.82
5.04

pKII

pKIII

pKIV

pKV pKVI

5.28*
4.46*
4.82*
4.20*
3.84*
3.89*
3.25*
3.51*
2.87*
2.73*
2.19*

5.87*
5.20*
4.70*
4.73*
4.44*
4.49*
3.97*
3.31*

6.21*
5.81*
5.63*
5.25*
4.78*

6.46*
5.89*

6.96*

8
Aminomalonic acid*
N-Butylaminoacetic acid
2-carboxyethyliminodiacetic acid
-carboxymethylaminopropionic
,-diaminobutyric
Di-(carboxymethyl)-aminomethyl
phosphonic acid
,-dimercaptosuccinic
Ethylenediamine-N,N-diacetic

3.32, 9.83
2.29, 10.07
2.06, 3.69, 9.66
3.61, 9.46
1.85, 8.24, 10.44
2.00, 2.25, 5.57, 10.76
2.40, 3.46, 9.44, 11.82
5.58, 11.05

Acid
pK
-hydroxybutyric
N-2-hydroxyethyliminodiacetic
3-hydroxypropyliminodiacetic
Iminodipropionic
Isobutyric*
Mandelic acid
2-Mercaptoethyliminodiacetic
Methyliminodiacetic

3.65
2.2, 8.73
2.06, 9.24
4.11, 9.61
4.86
3.41
-2.14, 8.17, 10.79
2.81, 10.18

9
pK
2-Methoxyethyliminodiacetic
2-Methylthioethyliminodiacetic
oxalic acid*
N-n-propylaminoacetic
N-2-sulfoethyliminodiacetic
-Bromobutyric acid
N-(carbamoylmethyl)-iminodiacetic acid
Cyanomethyliminodiacetic
,-diaminopropionic acid
Diethylaminoacetic
Dimethylaminoacetic
N-ethylaminoacetic
Gluconic*
-hydroxybutyric
-hydroxypropionic
Iminodiacetic*
-iodopropionic*
N-isopropylaminoacetic
-mercaptobutyric
N-methylaminoacetic
Nitrilotriacetic
2-Phosphonoethyliminodiacetic
Thermodynamic

PHENOLS
Compound
Chromotropic acid
o-Methoxyphenol
o-Hydroxybenzaldehyde
2-Amino-4,5 dimethylphenol hydrochloride
4,5-dihydroxybenzene1,3 disulphonic acid
Resorcinol
p-Methoxyphenol
3-Hydroxyanthranilic
acid
2-Aminophenol
hydrochloride
Kojic acid

2.2, 8.96
2.1, 8.91
1.25, 4.14
2.25, 10.03
1.92, 2.28, 8.16
2.97
2.30, 6.60
3.06, 4.34
1.23, 6.69
2.04, 10.47
2.08, 9.80
2.30, 10.10
3.86
4.39
3.73
2.98, 9.89
4.04
2.36, 10.06
3.53
2.24, 10.01
3.03, 3.07, 10.
1.95, 2.45, 6.54, 10.46

pK

Ref.

5.36, 15.6
--, 9.93
7.95

6
50
50

10.4, 5.28

51

7.66, 12.6e
--, 9.15 (30o)
--, 10.16

50
50

10.09, 5.20

51

9.99, 4.86
9.40

51
77

Phenol

H(CH3)3 N+CH3SO2CH3CO-

9.95*
7.42

9.94*
8
9.33
9.19

8
7.83
8.05

CCl-3
CF3CHF2CH2 CHCl2 CHEC-

12.24, 11.80
12.37
12.74
12.89
13.55

Substituent Effects for Ionization of RCH2OH

R
pK
Ref.
64, 65
64
64
64
64

C2H5 O2 CC3H5 CH2 O2CBrFHOCH3CH3O-O2 C--O3PC6H5 2-Chloro-4-Nitro2-Nitro-4-ChloroO2 NNCCH3O2 Cn-C4 H9 O2 CIClCH3SHOCH2C2H5 H2 N-O3S--O3As
NO*Thermodynamic
*Reference 52

8.42*
8.81*
9.48
10.28*
9.93
10.2
9.93
723*

8.48*
9.53
9.92*
10.2
9.71

8.50*
8.41*
9.11*
9.28*
9.44
10.08
9.65
9.94*
9.9
9.59
5.42
6.46
8.35*
8.61**
9.17*
9.02*
9.53
9.83*
9.9
9.87
9.29

9.34*
9.95*
9.96
10.19*
10.20
9.39*
9.51
79
79
7.14*
7.95
8.47*
8.47*
9.38*
9.82*
10.0
10.30
9.03
8.37
6.35**

ALCOHOLS AND OTHER OXYGEN ACIDS

Alcohols
Compound
pK
Ref.
Choline
Chloral hydrate
Trifluoroethanol
CF3CH2 OH
CF3CH(OH)CH3
CF3CH2 (CH3)3OH
C3F7CH2 OH
(C3F7)2CHOH
HCCCH2 OH
C(CH2(OH))4
HOCH2CHOHCH2 OH
HOCH2CH2 OH
CH3CCH2 OH
CH3OH
CH2=CHCH2 OH
H2 O
CH3CH2 OH

13.9
9.66, 11.0
12.5
11.4, 12.43
11.8
12.43
11.4**
10.6**
13.55
14.1
4.4
14.77
14.82
15.54
15.52
15.74
16

6
61
62
63
63
10
63
63
64
64
64
64
64
64
64
64
64

10
H2ClCH3CCH2 HOCH2
HCH2=CHCH3-(extrap)
CF3C(CH3)2 OH
HOCH2CF2CH2 OH

14.31
14.8
15.1
15.5
15.5
(15.9)
11.6
11

64
64
64
64
64
64
64
64

Primary alcohols=RCH2OH and

Secondary alcohols in 50% alcohol
C2F5
C4F9
C5F11
C7F15
CHF2
CF2Cl
CHF2CF2
CHF2 (CF2)2
CF3 CH2
CF3 (CH2)2
CF3 CHMe OH
C3F7 CHMe OH
C3F7CHEt OH
C3F7CHPr OH
C3F7 CH(CF3) OH
C3F7CH(C2F5)OH
(C3F7)2CHOH
Carbonium ions

11.35
11.35
11.37
11.35
12.00
11.63
11.34
11.35

65
65
65
65
65
65
65
65

12.7

65

12.9
11.28
11.38
11.37
11.37
10.46
10.48
10.52

65
65
65
65
65
65
65
65

Triphenylmethanols in H2SO4 HC1O4 HNO3 Ref.

4,4,4-Trimethoxy
4,4-Dimethoxy
4-Methoxy
4-Methyl
4-Trideuteriomethyl3,3,3-Trimethyl-

.82.
-1.24
-3.40
-5.41
5.43
6.35

Unsubstituted triphenylmethanol
6.63
4,4;,4;-Trichloro4-NitroCCl3 CH2 OH
CF3CH2 OH
***50 aqueous ethanol

.82
-1.14
-3.59
-5.67
5.67
-5.95

-6.89
7.748.01
9.159.76
11.8***
11.3***

.80
-1.11
-3.41

66
66
66
66
66
66

6.60

66
66
66

Hydroxamic acids
Acid

pK

Ref.

FuroGlycine
HippuroisoNicotin
p-MethylbenzNicotin
Nicotin-methiodide
m-Nitrobenz-

8.45
7.40
8.80
7.85
8.90
8.30
6.46
8.07

72
72
72
72
72
72
72
72

11
Picolin
Pyrimidine-2-carboxSalicylTropo-

8.50
7.88
7.43
9.09

72
72
72
72

Other oxygen acids

Acid

pK

Ref.

4.6
12.84

18
77

12.92
12a
6.95a
13.48
13.29

77
77
77
91
91

Trimethylamine-n-oxide
Dimethylglyoxime
(50% dioxane)
O-methyl ether
Tropolone
-Bromotropolone
Acetald hydrate
Formald hydrate
a50% dioxane

OTHER OXYGEN ACIDS

Pyridine oxides
Compound
4-Aminopyridine 1-oxide
4-Dimethylaminopyridine 1oxide
4-Dimethylaminopyridine 1oxide
4-Dimethylamino-1-methoxypyridinium perchlorate
2-Methylaminopyridine 1-oxide
2-Amino-1-methoxypyridinium
perchlorate
4-Hydroxypyridine 1-oxide
4-Methoxypyridine 1-oxide
1-Methoxypyridi-4-one
2-Hydroxypyridine 1-oxide
2-Ethoxypyridine 1-oxide

pK
3.69

Ref.
67

3.88

67

3.88

67

>11
2.61

67
67

12.4
2.45
2.05
2.57
-0.8
1.18

67
67
67
67
67
67

12
Compound

pK

1-Methoxypyrid-2-one
4-Methylaminopyridine 1-oxide
4-Amino-1-methoxypyridinium
perchlorate
2-Aminopyridine 1-oxide
2-Dimethylaminopyridine 1-oxide
2-Methylamino-1-methoxypyridinium toluene-p-sulphonate
4-Benzyloxypyridine 1-oxide
1-Benzyloxypyrid-4-one
2-Methoxypyridine 1-oxide
1-Benzyloxypyrid-2-one

-1.3
3.85

67

>11
2.67
2.27

67
67
67

>11
1.99
2.58
1.23
-1.7

67
67
67
67
67

Pyridine 1-oxides
R

pK

Ref.

4-CH3
3-CH3
3,4-(CH)4
3-COOC4 H9
4-NO2
3-NH2
H
3-COOH
4-COOH

1.29
1.08
1.01
0.03
-1.7
1.47
0.79
0.09
-0.48

47
47
47
47
47
47
47
47
47

Hydroxamic acids
AcetoButyron-Butyrop-MethoxybenzoN-Hydroxyphthalimide 7.00, 6.10
Salicylo
Benzop-Chlorobenzo-NaphthoPropiono-

Ref.

pK

Ref.

9.40
9.48
9.00
9.19
71, 72
7.32
8.88
9.59
~7.7
9.46

68
68
68
68
68
68
68
68
68

Oximes
pK

Ref.

Benzophenone oxime

11.3

18

Diethyl ketoxime
Isonitrosoacetylacetone (INAA)
5-Methyl-1,2,3-cyclohexanetrione1,3-dioxime
Acetophenone oxime
Acetoxime

12.6
7.4

18
76

8.3
11.48
11.42

76
18
18

Isonitrosoacetone (INA)
Salicyclaldoxime (SA)
1,2,3-Cyclohexanetrionetrioxime
5-Methyl-1,2,3-cyclohexanetrionetrioxime

pK

Ref.

8.3
9.2

76
76

8.0

76

8.0

76

pK

Ref.

1.99
73
73
1.89
1.88
1.84, 2.16

73

pK

Ref.

9.4
8.2
8.2
7.1
8.1
5.18, 7.8
4.85

69
70
70
70
70
85
90

Oxygen acids
Sulfinic acids
p-Toluenep-Chlorobenzenep-Nitrobenzenep-Bromobenzenem-NitrobenzeneBenzene-

73
73
73

Peroxyacids
Peroxymonosulfuric
Acetic
n-Butyric
Formic
Propionic
peroxydiphosphoric
peroxymonophosphoric

13
Peroxides ROOH
H
11.6

Ref. 70

CH3
11.5

Oximes

C2H5
11.8

Ref. 93

benzoquinoline mon3-pyridine-1,2-ethanedione-2-oxime
methiodide
Pyridine-2-aldoxime heptiodide
Pyridine-4-aldoxime methiodide
Pyridine-4-aldoxime pentiodide
4-Pyridine-1,2-ethanedione-2-oxime
methiodide
Pyridine-2-aldoxime methiodide
PhenylglyoxaldPyridine-4-aldoxime dodeciodide
Pyridine-3-alkoxime methiodide

Hydroxamic acids

iso-C3H7
12.1

pK
6.25
7.20
8.00
8.50
8.50
7.1
8.0
8.3
8.5
9.2

Ref. 93
pK

D-LysineN-phenylnicotinoChloroacetoFormop-Chlorophenoxyacetop-Hydroxybenzop-MethoxybenzoN-Phenylbenzoo-AminobenzoL-Tyrosine
L-Lysine
p-Nitrobenzop-AminobenzoL-LactiPropionoPhthaloIndole-3-acetoCyclohexanoHexano-

Amino Acids
Compound
Alanine
-Aminobutyric acid
-Aminoisobutyric
Argininosuccinic

Compound
Hydroxyproline
Leucine
Methionine
1-Methylhistidine
Norleucine

7.93
8.00
8.40
8.65
8.75
8.93
9.00
9.15
9.17
9.20
7.9
8.0
9.3
9.3
9.4
9.4
9.5
9.7
9.7

pK
-COOH -NH3
2.35
2.55
2.36
>12, 1.62
2.70, 4.26

9.69
9.60
10.21
9.58

pK
-COOH -NH3
1.92
2.36
2.28
6.48, 1.69
2.39

9.73
9.60
9.21
8.85
9.76

Ref.
6
6
6

Ref.
6
6
6
6

tert-C4 H9
12.8

Compound

iso-C4H9
12.8

pK
-COOH -NH3

Ref.

Diidotyrosine
Glutamic acid
Glycine
Histidine
Hydroxylsine

2.09, 3.86
10.3, 9.20
4.84
1.65
2.26
6.48, 2.12
2.19, 4.25
2.34
6.0, 1.82
2.13

Isoleucine
Lysine

2.36
2.18

6
6

Aspartic acid
Canaline
Creatinine
Cystine

O-Methyl tyrosine
O-Methyltyrosine ethyl
ester
7.31
octopine
13, 1.36
2.40
Phenylalanine
1.83
2-Pyrrolidoone-5-carboxylic
acid (glucamic acid) 3.32
Serine
2.21
Threonine
2.63
N-Trimethyl tyrosine
Tyrosine
10.07, 2.20
Urocanic acid
5.8
Valine
2.32
-Alanine
3.60
-Aminobutyric acid
4.23
Arginine 12.48
2.17
Asparagine
2.02
Azaserine
8.55
Canavanine
7.40, 9.25
Creatine
2.67
Cysteine 10.78
1.71
3,4-Dihydroxyphenylalanine
9.88, 2.36
11.68
Glutamine
2.17
Histamine 5.0
-Hydroxyglutamic
2.09
acid
4.18

9.82
11.6 (?)
9.2
7.85
9.85
7.82
9.67
9.6
9.17
8.62
9.67
9.68
8.95
10.53
9.27

6
6
6
6
6
6
6
6
6
6

21

8.77

22
6

9.13

9.15
10.43
9.75
9.11
3.5
9.62
10.19
10.43
9.04
8.8

6
6
21

8.68

9.13
9.7
9.20

6
6
6

6
6
6
6
6
6
11.50 (?) 6
11.02
6
8.33
6

14
Norvaline
Ornithine

2.36
1.71

Proline
Sarcosine
Taurine 1.5
Thiolhistidine

1.99
2.23

Tryptophan
Tyrosine ethyl ester

Peptides
Compound
Anserine 7.0
Carnosine 6.83
Cystinyldiglycine
Glycylglycine
Gly-gly-gly
Glycylproline
Aspartyl histidine
Diglycylcystine
Glutathione 9.12
Gly-gly-gly-gly
Lysyl-lysine (L,L)

9.76
8.69
10.76
10.60
10.01
8.74

<1.5, 11.4
1.84
8.47
2.38
9.39
7.33
9.80

pK
-COOH -NH3
2.65
-3.12
3.12
3.06
3.26
2.84
2.45
6.82
2.71
2.12
3.53
3.05
3.01
10.05

6
6
6
6
6
6
6
22

Ref.

9.5
9.51
6.36
6.95
8.13
7.91
8.55
7.98
3.02
7.94
8.66

6
6
6

7.75
7.53
11.01

23
6

23
6
6
6

Compound

-COOH

GlyAla (L) or (D)

AlaGly (L) or (D)
GlyAlaAla (LL)
GlyAlaAla (LD)
AlaAlaOH (DD)
AlaAlaOH (LD)
HAlaAlaAlaOH (3L)
HAlaAlaAlaOH (LLD)
HAla-Ala-AlaOH (LDL)
HAla-Ala-AlaOH (DLL)
H-Ala-Ala-AlaOH (3D)
HAla-Ala-Ala-AlaOH (4L)
HAla-Ala-Ala-AlaOH (LLDL)

3.17
3.16
3.38
3.30
3.30
3.12
3.39
3.37
3.31
3.37
3.39
3.42
3.24

Compound

-COOH

HAla-Ala-Ala-AlaOH (LDLL)
HAla-Ala-Ala-AlaOH (DLLL)
HLys-AlaOH (LL)
HLys-AlaOH (LD)
HAla-Lys-AlaOH (3L)
HAla-Lys-AlaOH (LDL)
HAla-Lys-AlaOH (LLD)
HAla-Lys-Ala-AlaOH (4L)
HAla-Lys-AlaOH (LDLL)
HAla-Lys-Ala-Ala-AlaOH (5L)
HAla-Lys-Ala-Ala-AlaOH (LDLLL)
HLys-LysOH (LL)

3.22
3.42
3.22
3.00
3.15
3.33
3.29
3.58
3.32
3.53
3.30
3.01

-NH2

-NH2

-NH2

-NH2 Ref.

-NH2

-NH2

-NH2

-NH2 Ref.

10.70
10.63
10.30
10.36
10.49
10.58
10.37
10.35
10.29
10.05

11.01

8.23
8.24
8.10
8.17
8.14
8.30
8.03
8.05
8.13
8.06
8.06
7.94
7.93
7.99
7.99
7.62
7.74
7.65
7.97
7.84
8.01
8.01
7.75
7.85
7.53

27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27
27

15
HLys-LysOH (LD)
HLys-LysOH (3L)
HLys-Lys-LysOH (LDL)
HLys-Lys-LysOH (LDD)

2.85
3.08
2.91
2.94

7.53
7.34
7.29
7.14

9.92
9.80
9.79
9.60

10.98
10.54
10.54
10.38

Compound

pK

Ref.

Glutathione
Glycylserine
Glycylleucine
Leucylglycine
Glycylisoleucine
Leucylglycylglycine
Glycylphenylalanine
Glycyltyrosine
Benzylglutamic acid
Glycyltryptophane
Glutathione, oxidized
Alanylalanine (LL)
Alanylalanine (LD)
Lysylalanine (LL)
Lysylalanine (LD)
Leucyltyrosine (LL)
Leucyltyrosine (DL)
Lysyllysine (LD)

3.59, 8.75, 9.65

8.23
8.13
7.96
7.96
7.66
8.28
8.22
3.49, 4.99
8.04
3.15, 4.03, 8.57, 9.54
3.30
3.12
3.22
3.00
3.46
3.12
2.85

77
77
77
77
77
77
77
77
77
77
77
92
92
92
92
92
92
92

NITROGEN COMPOUNDS
Aliphatic Amines
pK

Ref.

Ammonia

9.21

PRIMARY AMINES
-Alanine ester
AllylamineBenzyl
n-Butylt-ButylCyclohexylmethylEthanolEthylenedi-

9.13
9.69
9.34
10.59
10.55
10.49
9.50
9.98, 7.52

1
2
1
1
1
1
1
1, 77

Aliphatic Amines

pK

Hydrazine
8.10
Isopropyl10.63
Methyl10.62
Phenylamyl10.49
-Phenylethyl9.83
n-Propyl10.53
Trimethylsilymethyl10.96
CH3ONH2
4.60
Allyl9.49
-Amino-n-butyric acid ester 9.71
sec-Butyl10.56
Cyclohexyl10.64
-difluoroethyl7.52
Ethyl
10.63
Glycine ester
7.75
Hydroxyl5.97
Methoxy4.60
neo-Pentyl10.21
-Phenylbutyl
10.40

Ref.
1
1
1
2
1
1
1
12
1
1
1
1
1
1
1
1
1
1
2

8.14
8.30
7.62
7.74
7.84
8.38
7.53

10.70
10.63
10.09
10.35
9.92

11.32
11.42
11.09

27
27
27
27

16
10.20
8.8*

-PhenylpropylTriethylenedi-

X
HHF2CRO2CHOC6H5 H2 NH2C=CHCH3-

1
?

XNH3+ XCH2NH3+ X(CH2)2NH3+ X(CH2)3NH3+ X(CH2)4NH3+

9.25*
5.96*
4.58*
8.12*
10.64*

X-NH3+
X(CH2 )2NH3 +
X(CH2 )2NH3 +
X(CH2 )4NH3 +
X(CH2 )5NH3 +
X(CH2 )8NH3 +
X(CH2 )10NH3+
X(CH2 )3NH3 +

10.64*
7.52
7.75
9.37*
9.69
10.67*

-Cyclohexylpyrroline
-(p-Tolyl)pyrroline
-Ethylpyrrolidine
-Benzylpyrrolidine
N-methylhydroxylamine
DiethylDi-n-butylDiisobutyl-Ethylpyrroline
-Benzylpyrroline2-Methylpiperidine
-Cyclohexylpyrrolidine
-(p-Tolyl)pyrrolidine
N,O-dimethylhydroxylamine
Acetanilide
*thermodynamic value

Aliphatic Amines
1,2-Iminoethane
cis-2,3-Iminobutane
1,2-Imino-2-methylpropane
1,2-Iminobutane
trans-2,3-Iminobutane

Secondary Amines

10.15*

10.37

10.20*
10.65*

10.39*
10.84*

10.49*
11.05*

2
2

10.61*

10.63*

10.64*

-SO3

9.77
10.19
10.77
10.75

1
5.75
9.20
10.65
10.95

-PO3

11.35
10.05

11.25

10.43

10.61*

9.13
9.50*
9.83*
9.98*

9.71

10.58*

-NH3+

9.25*
10.64
10.67
10.61
10.63
10.65
10.64
10.58

DimethylDi-n-propylDiisopropylt-Butylcyclohexyl-

Ref.

10.63*

10.58*

-H

Secondary amines

X(CH2)5NH3+

10.67*

-.88

9.31
9.74
10.10
8.59

pK

Ref.

10.64
11.00
11.05
11.23

1
1
1
1

pK

Ref.

7.95
7.59
10.43
10.36
5.96
10.98
11.25
10.50
7.43
7.08
10.99
10.80
10.01
4.75
+0.61

2
2
2
2
12
1
1
1
2
2
2
2
2
12
4

-CO2

AllylmethylBenzylethylMorpholine
N-Benzoylpiperazine
Di-sec-butylN-Methylmethoxyamine
Pyrolidine
1-Tosylpiperazine
BenzylmethylPiperidine
N-Carbethoxypiperazin
DietrimethylsilylmethylDiallylN-MethylhydroxylTrimethyleneimine
Cis-2,6-dimethyl-piperidine

10.25
10.8
10.8
10.9
11.0

Ref.
2

pK

Ref.

10.11
9.68
8.36
7.78
11.01
4.75
11.27
7.39
9.58
11.22
8.28
11.40
9.29
5.96
11.29
10.92

1
1
1
1
1
1
1

pK

Ref.

9.76
10.29

1
1

1
1
1
1
1
1
1
3

Tertiary Amines
pK

Ref.

7.98
8.72
8.61
8.29
8.69

7
7
7
7
7

TrimethylDimethyldiethylDimethyl-n-propylDimethyl-isobutylDimethyl-sec-butyl-

pK

Ref.

9.99
9.91
10.40

1
1
1

17
Tri-n-propyl10.65
Triallyl8.31
N-Allylpiperidine
9.69
1-Diethylamino-hexane-thiol-(6)
Methyl--diethylamino-ethyl-sulfide
1,2-Dimethyl-2 -pyrroline
11.94
1-methyl-2-n-butyl-2 -pyrroline 11.90
1-Ethyl-2-methyl-2-pyrroline
11.92
1-n-Butyl-2-methyl-2-pyrroline 11.90
1,2-Dimethyl-2 -tetrahydropyridine
11.57
N-Ethyl derivative of:
1,2-Imino-ethane
7.93
Trans-2,3-Iminobutane
9.47
Trimethylhydroxylamine
3.65
Dimethylethyl9.99
Triethyl10.65
Dimethyl-n-butyl10.02
Dimethyl-isopropyl10.30
Dimethyl-t-butyl10.52
Tri-n-butyl10.89
Diallylmethyl8.79
1-n-Propylpiperidine
10.48
10.1
10.1

pK

1
1
2
2
2
2
2
7
7
12
1
1
1
1
1
1
1
2
5

Ref

EtN(CH2CH2 CN)2
4.55
8
H2 NCH2CN
5.34
8
N-Amphetamine-(CH2)2-CN
7.23
8
N-Norcodeine-(CH2)2CN
5.68
8
Dimethylcyanimide
1.2
9
Diethylcyanimide
1.2
9
Aminoacetonitrile
5.3
9
Diethylaminoacetonitrile
4.5
9
2-Amino-2-cyanopropane
5.3
9
-Isopropylaminopropionitrile
8.0
9
-Diethylaminopropionitrile
7.6
9
Et2 NCH2 CN
4.55
8
Et2 N(CH2)3CN
9.29
8
Et2 N(CH2)5CN
10.46
8
HN(CH2CN)2
0.2
8
HN(CH2CH2 CN)2
5.26
8
N(CH2CH2 CN)3
1.1
8
N-piperidine-C(CH3)2CN
9.22
8
N-Methamphetamine-(CH2)2 CN 6.95
8
Methyl cyanamide
1.2
9
Ethyl cyanamide
1.2
9
Cyanamide
1.1
9
Dimethylaminoacetonitrile
4.2
9
-Aminopropionitrile
7.7
9
-Dimethylaminopropionitrile
7.0
9
,"-Dicyanodiethylamine
5.2
9
For complex chelating agents of aliphatic amines, see also ref. 77.

Fluoro-substituted amines
CF3CH2 NH2
CF3CH2 N(CH3)2

pK

Ref.

5.7
4.75

10
10

9.8
1,2-Dimethylpyrrolidine
1-Methyl-2-n-butylpyrrolidin
1-Ethyl-2-methylpyrrolidine
1-n-Butyl-2-methylpyrrolidine
1-Ethyl-2-methylpyrrolidine
1,2-Iminobutane
cis-2,3-Iminobutane
N-dimethylhydroxylamine
Allyldimethyl
1,2-Dimethylpiperidine
1-Ethyl-2-methyl-2-tetrahydropyridine

-10.26
10.24
10.64
10.43
10.70
8.18
8.56
5.20
8.78
10.26

5
2
2
2
2
2
7
7
12
1
2

11.57

Cyanoamines
N-piperidine-CH2CN
Et2 NCN
Et2 N(CH2)2CN
Et2 N(CH2)4CN
Et2 NC(CH3)2 CN
EtN(CH2CN)2

pK

Ref

4.55
-2.0
7.65
10.08
9.13
-0.6

8
8
8
8
8
8

18
CF3CH2 NHCH3

6.05

10

pK

Ref.

Phenylethylamines
2-phenylethylamine
9.78
N-methyl-2-(3,4-dihydroxyphenyl)ethylamine
8.78
N-methyl-2-phenyl
10.31
Epinephrine
8.55
Arterenol
8.55

11
11
11
11
11

R1
CHCH2NHR4

R2

R1

H
H
R1
H
OH
H
OH
OH
H
H
H
OH
H
OH
OH

R2

H
H
R2
OH
H
OH
OH
OH
H
H
OH
H
OH
OH
OH

R3

R3

R4

H
OH
R3
OH
OH
H
H
OH
H
OH
OH
OH
H
H
OH

H
H
R4
H
H
H
H
H
CH3
CH3
CH2
CH3
CH3
CH3
CH3

Ring amines and imines (in 80% methyl

cellosolve) (Ref. 2)
pK
Pentamethylene
Hexamethylene
Heptamethylene
Octamethylene
Nonamethylene
Decamethylene
Undecamethylene
Dodecamethylene
Tridecamethylene
Tetradecamethylene
Hexadecamethylene
Heptadecamethylene
Cyclohexyl
Cycloheptyl
Cyclooctyl
Cyclononyl
Cyclodecyl
Cycloundecyl
Cyclododecyl
Cyclotridecyl
Cyclotetradecyl
Cyclopentadecyl

9.99
10.00
9.77
9.39
9.14
9.04
9.14
9.31
9.35
9.35
9.29
9.27
9.82
9.99
9.95
9.85
9.71
9.62
9.63
9.54
9.54

ref. 11

pK
9.78
8.90

pK
8.81
8.67
9.22
8.93
8.58
10.31
9.31
8.62
8.89
9.36
8.78
8.55
Cycloheptadecyl
Cyclooctadecyl

Amines other
Dimeoone
Phthalimide
Nitrourea
Nitrourethane
Diphenylthiocarbazone
,,"-Triaminotriethylamine

9.57
9.54

pK

Ref.

5.23
8.30
4.57
3.28
4.5

18
18
18
18
6

8.42, 9.44, 10.13

87

19
Anilines
Monosubstituted
Substituent o
H4.62*
(CH3)3 N+CH3O2 C2.16
CH3SO2CH3SBr2.60*
F2.96*
CH3O4.49*
C6H5 3.78*
(CH3)3C3.78
O S3
H3 N+
1.3
O2 N-0.28*
HO2C2.04
C2H5 O2 C2.10
F3CHO4.72
Cl2.62*
(CH3)3SiC2H5 O4.47*
CH34.38*
HO As
3.77
3
H2 N4.47
*Thermodynamic

Ref. 2

m-(CH3 )3Sio-CH3 Oo-CH3

p-CH3
p-CH3 CH2CH2p-(CH3)2CHp-(CH3)2CHCH2p-(CH3)3Cm-Brm-Clp-Fp-(CH3)3Sip-CH3 O-

4.64*
2.26
3.56
2.68*
4.05
3.51*
3.38*
4.20*
4.18

4.58*
2.51
2.30
1.48
4.40
3.91*
4.52*
5.29*
4.27*

3.80
2.65
2.45*
3.05

3.32
3.29
0.98*, 1.11*
2.32
2.38
2.57*
5.50
3.81*
4.36*
5.25*
5.07*
4.05
6.08

3.49*
4.17
3.32*
4.64*
4.17*
4.67*
4.05
4.88

Dimethyl
H
m-NO2
m-CN
p-NO2
p-CN
p-NO

pK

Ref.

5.07
2.63
2.97
0.61
1.78
4.54

52
52
52
52
52
52

Dimethyl (in 50% ethanol)

Substituent XC6H4N(CH3)2
pK
Hm-CH3
p-C2 H5o-(CH3)2 CHp-CH3 CH2CH2 CH2o-(CH3)3 Cp-Ip-Brp-Cl-

4.21, 4.09
4.66
4.69
5.05
4.62
4.26
3.43, 2.73
3.52, 2.82
3.33

2-NH2-1-NO22-NH2-3-NO22-NH2-4-NO22-NH2-5-NO22-NH2-6-NO2-

-1.0
2.93
2.63
3.16
2.75

pK
pK

Ref. 2

4.41
5.49
5.15, 5.07
4.94
4.43
4.77
4.19
4.65
3.08
3.09
4.01
3.99
5.14, 5.16

Ortho-substituted anilines (in 50% ethanol)

pK

H2-CH32,3-(CH3 )22,4-(CH3 )22,5-(CH3 )22,6-(CH3 )23,5-(CH3 )22-CH32-(CH3)2CH2-(CH3)2C2,6-(CH3 )2-4-(CH3)3C2,4-(CH3 )2-6-(CH3)32-CH3-4,6-(CH3)3 C2,4,6-[(CH3)3C3 ]-

4.25
3.98, 4.09
4.42
4.61
4.17, 4.23
3.42, 3.49
4.48
4.09
4.06
3.38
3.88
3.43
3.31
<2

Substituted Naphthylamines
pK
1-NH21-NH2-2-NO21-NH2-3-NO21-NH2-4-NO21-NH2-5-NO21-NH2-6-NO21-NH2-7-NO21-NH2-8-NO21-NH2-8-SO31-NH2-3-SO31-NH2-4-SO31-NH2-5-SO31-NH2-6-SO31-NH2-7-SO31-NH2-8-SO32-NH2-

3.92*
-1.6
2.22
0.54
2.80
3.15
2.83
2.79
1.71
3.20*
2.81*
3.69*
3.80*
3.66
5.03*
4.11*

20
2-NH2-7-NO22-NH2-8-NO22-NH2-1-SO32-NH2-3-SO32-NH2-4-SO32-NH2-5-SO32-NH2-6-SO32-NH2-7-SO32-NH2-8-SO3-

3.13
2.86
2.35
-3.70
3.96*
3.74*
3.95*
3.89*

N-substituted anilines*
R
HCH3C2H5 n-C3 H7n-C4 H9i-C4 H9sec-C4 H9 t-C6 H12CyclopentylCyclohexylt-C4 H9*Thermodynamic

AMINES
Primary amines

C6 H5 NHR
4.58
4.85
5.11
5.02
4.95
--6.30
5.30
5.60
6.95

C6 H5 N(CH3)R
4.85
5.06
5.98
--5.20
6.04
-6.71
6.35
7.52

C6 H5 NR2
4.58
5.06
6.56
5.59
~5.7
-------

2-CH3 C6 H4 NHR
4.39
4.59
4.92
-----5.07
5.34
6.49

2-CH3 C6 H4 NR2
4.39
5.86
7.18

Ref. 77
pK

2-aminoethylsulphonic acid
Aminomalonic acid
N-n-butylethylenediamine
2,3-diaminobutane, meso
2,3-diaminobutane, racemic
2,2'-diaminodiethyl sulfide
1,3-diamino-2,2-dimethylpropane
N,N'-Di-(2-aminoethyl)-ethylenediamine
1,2-diamino-2-methylpropane
1,3-Diaminopropan-2-ol
N,N'-Diglycyethylenediamine
Ethylenediamine-N,N-diacetic acid
Furfurylamine
2-(2-hydroxypropylamino)-ethylamine
2-(3-hydroxypropylamino)ethylamine
N-Methylaminoacetic acid
Methyl--amino--mercaptoproionate
N-n-propylethylenediamine
1,2,3-triaminopropane
9.59
Tris-(hydroxymethyl)-aminomethane
2-amino-2'-hydroxydiethyl sulfide
N-(carbamoylmethyl)-iminodiacetic
acid
2,2'-diaminodiethylamine
9.65
2,3-diamino-2,3-dimethylbutane

9.08
3.32, 9.83
7.53, 10.30
6.92, 9.97
6.91, 10.00
8.84, 9.64
8.18, 10.22
3.32, 6.67, 9.20, 9.92
6.79, 10.00
8.23, 9.68
7.63, 8.35
5.58, 11.05
8.89
6.94, 9.86
6.78, 9.76
2.24, 10.01
3,3'-diaminodi-n-propylamine
pK
10.7
6.56, 8.99
1,2-Di-(2-aminoethylthio)ethane
7.54, 10.34
1,2-diaminopropane
3.72, 7.95,
N,N-diethylethylenediamine
N,N-dimethylethylenediamine
8.10
N-Ethylethylenediamine
9.04
N-(2-hydroxyethyl)-ethylenediamine
N-isopropylethylenediamine
2.30, 6.60
2-Methoxyethylamine
3.58, 8.86,
Mercaptoethylamine
N-Methylethylenediamine
6.56, 10.13

8.02,9.70,
8.43, 9.32
7.13, 10.00
7.07, 10.02
6.63, 9.53
7.63, 10.56
6.83, 9.82
7.70, 10.62
9.20
8.27, 10.53
7.56, 10.40

21
2-Methylthioethylamine
2-thienylmethylamine
Triaminotriethylamine
10.29

9.18
8.92
8.56, 9.59,

Secondary Amines
pK
N-Butylaminoacetic acid
N,N'-Diethylethylenediamine
2,2'-dihydroxydiethylamine
N,N'-di-n-propylethylenediamine
Ethylenediamine-N,N'-diacetic acid
Iminodipropionic acid
Piperazine
-carboxymethylaminopropionic acid
N,N'-Dimethylethylenediamine
N-ethylaminoacetic acid
Iminodiacetic acid
N-isopropylaminoacetic acid
N-n-propylaminoacetic acid

2.29, 10.07
7.70, 10.46
9.00
8.14, 10.97
6.42, 9.46
4.11, 9.61
5.68, 9.82
3.61, 9.46
7.40, 10.16
2.30, 10.10
2.98, 9.89
2.36, 10.06
2.28, 10.03

Tertiary Amines
pK

Ref. 5
pK
N-Dimethyl-cysteamine
N-Dipropyl-cysteamine
N--Mercaptoethyl-morpholine
1-Diethylamino-butan- (4)
Methyl-[-diethylamino-ethyl]sulfide
N-Diethyl-cysteamine
N--Mercaptoethyl-piperidine
1-Diethylamino-propan- (3)
1-Diethylamino-hexan- (6)

ANILINES

Ref. 88
pK

m-Substituted anilines
m-C2 H5
-C(CH3 )3
3,5-[C(CH3)3]2
m-CN

4.70
4.66
4.97
2.76

3-OCH3.5-NO2
3,5-Br2
m-CH(CH3)2
3,5-(CH3 )2
m-COCH3
3-Cl,5-OCH3
3,5-(OCH3 )2

2.11
2.34
4.67
4.74
3.56
3.10
3.82

pK

4-(2-aminoethyl)morpholine
Di-(2-hydroxyethyl)aminoacetic acid
Hexamethylenetetramine

4.84, 9.45
8.08
5.13

Methyliminodiacetic acid
Diethylaminoacetic acid
Dimethylaminoacetic acid

2.81, 10.18
2.04, 10.47
2.08, 9.80

NAPHTHALAMINES

pK

substituted naphthalamines
2-naphthalamine X

N-2-hydroxyethyliminodiacetic acid
Triethylenediamine

Ref. 1
Diallylmethyl
Benzyldimethyl
N-Allylpiperidine
N-Allylmorpholine
Propargyldimethyl
Propargylethyldimethyl
N-Methylmorpholine
N-Methylpyrrolidine
N,N-Dimethylhydroxylamine
Allyldimethyl
Benzyldiethyl
N-Ethylpiperidine
N-Ethylmorpholine
Propargymethyldimethyl
N-Methylpiperidine
N-Methyltrimethyleneimine
Triethanolamine
N,N-Dimethylmethoxyamine

pK

2.2, 8.73
4.18, 8.19

1-NH2 ,3-X

pK
8.79
8.93
9.68
7.05
7.05
8.88
7.41
10.46
5.20
8.73
9.48
10.40
7.70
8.33
10.08
10.40
7.77
3.65

7.95, 10.7
8.00, 10.8
6.65, 9.8
10.1
9.8
7.8, 10.75
7.95, 11.05
8.0, 10.5
10.1

2-NH2 ,5-X
1-NH2 ,5-X

1-NH2 ,7-X

1-NH2 ,2-X
1-X,2-NH2
1-NH2 ,8-X
2-naphthalamine

NO2
CN
Cl
Br
I
COOCH3
OCH3
OH
CH3
Cl
NO2
OH
NO2
OH
Cl
NH2
NO2
Cl
OCH3
OH
NO2
NO2
NO2
X

Ref. 88
pK
4.16
2.07
2.26
2.66
2.67
2.82
3.12
3.26
3.30
3.96
2.71
3.01
4.07
2.73
3.96
3.34
4.21
2.55
3.48
4.07
4.20
-1.74
-0.85
2.79

22
2-NH2 ,4-X

1-NH2 ,6-X

2-NH2 ,7-X

2-NH2 ,6-X
2-NH2 ,8-X
1-NH2 ,4-X
2-NH2 ,3-X

NO2
CN
Cl
Br
I
COOCH3
OCH3
NO2
Cl
OCH3
OH
NO2
Cl

2.43
2.66
3.38
3.40
3.41
3.38
4.05
2.89
3.48
3.90
3.97
3.10
3.71

OCH3
OH
NH2
NO2
OCH3
NO2
NO2
Br
NO2

4.19
4.25
4.66
2.62
4.64
2.73
0.54
3.21
1.48

pK

Anilines (in 50% ethanol)

Unhindered

pK

Ref.

Aniline
p-Aminodiphenyl
2-Naphthylamine
3-Phenanthrylamine
m-Aminodiphenyl
2-Aminofluorene
2-Phenanthrylamine
2-Anthrylamine

4.19
3.81
3.77
3.59
3.82
4.21
3.60
3.40

40
40
40
40
40
40
40
40

Hindered

pK

Ref.

o-Aminodiphenyl

3.03

40

peri

pK

Ref.

1-Naphthylamine
9-Phenanthrylamine
3-Aminopyrene
1-Phenanthrylamine
1-Anthrylamine

3.40
3.19
2.91
3.23
3.22

40
40
40
40
40

meso

pK

Ref.

9-Anthrylamine

2.7

40

o-Aminophenols

pK

Ref.

3-Hydroxyanthranilic acid
10.09, 5.20
2-Aminophenol hydrochloride 9.99, 4.86

51
51

Indicators

pK

Ref.

p-Aminoazobenzene
4-Chloro-2-nitroaniline
4,6-Dichloro-2-nitroaniline

2.82, 2.76 60
-1.02, -1.03 60
-3.61, -3.32 60

6-Bromo-2,4-dinitroaniline
-6.64, -6.71
2-Amino-4,5-dimethylphenol
hydrochloride
10.40,5.28
N,N-Dimethyl-2,4-dinitroaniline -1.00, -p-Nitrodiphenylamine -2.4 to -2.9, -2.50
4-Methyl-2, dinitroaniline -3.96, -4.44

51
60
60
60

Heterocyclics
Nucleosides, etc.

pK

Ref.

4.15, 9.80
3.81, 6.17
3.74, 5.92
3.95, 6.3
4.00 (4.1), 6.5
7.85, 12.7
4.45, 12.2
4.25
4.16-4.31, 6.04
4.44
4.8, 6.6
3.3, 9.2, 12.3
2.2, 9.5
1.6, 9.16, 12.5
2.4, 9.4, 6.1
2.9, 9.6, 6.3
1.98, 8.94, 12.10
8.9, 1.54, 6.04
4.6, 12.4

6
6
6
36
36
37
6
6
6
6
6
6
6
35
6
6
6
6
6

4.4
9.75
8.5 (8.1), 11.3
3.63
3.3, 12.5
3.3, 6.1
3.74, 6.2-6.4
3.9, 12.5
4.11
4.22, 12.5
4.3-4.4, 6.19*
4.5, 6.3
4.6, 6.4
5.09, 10.77
4.51, 8.99
1.6-2.2, 9.16-9.5
2.3, 9.36, 0.7, 5.9
2.9, 9.7, 6.4
3.3, 9.3, 6.5
1.2, 8.9
8.75, 12.5

6
37
38
6
35
36
6
37
6
35
6
6
6
6
6
6
6
6
6
6
6

4.5, 13.0
9.95
7.7, 12.05
8.5 (8.3)
6.3

6
37
38
38
38

Adenine
2'-AMP
3'-AMP
ADP
ATP
Barbital
Cytosine
Cytosine (deoxy)
3' CMP
CDP
CDP, (deoxy)
Guanine
Guanosine
"
5'-GMP
GDP
Hypoxanthine
5'-IMP
5-Methylcytosine
5-Methylcytosine deoxyriboside 5'-phosphate
3-Methyluracil
3-Methylxanthine
Adenosine
"
5'-AMP
Barbituric acid
Cytidine
"
2'-CMP
5'-CMP
CTP
2,6-Diaminopurine
Isoguanine
Guanosine (deoxy)
GMP (2' + 3')
5'-GMP (deoxy)
GTP
Inosine
"
5-Methylcytosine deoxyriboside
1-Methyluracil
1-Methylxanthine
7-Methylxanthine
9-Methylxanthine

23
Purine
Thymidine
5'-TMP
Uracil deoxyriboside
5'-UMP
UTP
Uridine
"
Xanthosine
Orotic acid
Pyrimidine
Thymine
Uracil
UMP (2' + 3')
UDP
Uric acid
Xanthine
"

pK

Ref

2.52, 8.90
9.8
10.0, 1.6, 6.5
9.3
9.5, 6.4
9.5, 6.6
9.25
9.17, 12.5
0, 5.5, 13.0
2.8, 9.45, 13
1.30
0, 9.9, 713.0
.5, 9.5, 13.0
9.43, 1.02, 5.88
9.4, 6.5
5.4, 10.3
0.8, 7.44, 11.12
7.2

37
6
6
6
6
6
6
35
6
6
37
6
6
6
6
6
6
38

24
Heterocyclic Bases (Ref. 2)
5

6
7

Isoquinoline 5.14*

Pyridine 5.14*
pK (20)

Quinoline 4.85*

N
9

10

7,8-Benzoquinoline
4.25*

5,6-Benzoquinoline
5.15*

Acridine 5.60

3,4-Benzacridine 4.70*

1,2-Benzacridine 3.45a
N

N
N

Pyridazine 2.10*

Cinnoline 2.64*

N
Pyrazine 0.37*

Pyrimidine 1.10*

N
N

Phenanthridine 3.30a

2,3-Benzacridine 4.52a

Benzoquinoline 5.05*

N
N
Quinazoline 3.31*

Phthalazine 3.39*

50% EtOH

Heterocyclics

pK

Ref.

Aureomycin
Iridine
3-Hydroxy
5-Hydroxy (acridone)
5-Methoxy

3.30, 7.44, 9.27

--, 5.62
8.81, 5.52
--f, -0.32
--, 7

77
39
39
39
39

N
N
Quinoxaline 0.6*

25
Acridine
H-H2 N-HO-CH3-H2K-(1-CH3 --)-1,9-(CH3 )2-a 50% ethanol; ref. 39

Ref. 2
1-5.60*
4.40*
3.59a
4.18a
10.7a
3.95a

2-4.11a
8.04*
7.61a
4.86a
9.9a

2.88a

8-amino-1,2-benzacridine
2-amino-4-methyl-5,6-benzoquinoline
3-amino-6,7-benzoquinoline
8-amino-3,4-benzacridine
1'-amino-5,6-benzoquinoline
4'-amino-5,6-benzoquinoline
2-amino-4-methyl-7,8,benzoquinoline
6,7-benzoquinoline
5,6-benzoquinoline
4-amino2-methyl4-amino-2-methyl2-amino-4-methyl4'-amino3'-amino1'-amino2',4'-diaminoBenziminazole
2-aminoBenztriazole
Benzthiazole
2-aminobenzoxazole
2-amino2,3-benzacridine
5-amino5-acetamido7-amino5-amino-6:7:8:9-tetrahydroCaffeine
cinchonine
Cinnoline
4-aminoCocaine

pK

Ref.

6.72

40

7.14
4.78
7.42
5.03
5.20

40
40
40
40
40

6.74
5.05, 3.84a
5.15, 3.90a
7.99a
4.44a
8.45a
7.14, 6.51a
5.20, 4.10a
4.02a
5.03
4.91a
5.53
7.54
1.6
1.2, 0.1a
4.51
(decomp.)
3.73
4.52a
9.72a
4.56a
5.38a
9.66a
0.61
7.2
2.70
6.84
7.6

40
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
4
4
19
19
4

3--

4--

5--

9--

5.88*
5.03a
5.5239
8.8139
4.60a

6.04*
5.50a
4.45a
9.4*

9.99*
9.45a
-.3239
>12
4.70a
9.73s

3.22a

4.79a

26
Cinnoline 4-hydroxy
6-hydroxy
-hydroxy
,'-dipyridyl
4-amino4-amino-2-methyl4-amino-2-methyl-8-chloro8-chloro3,4-diamino3-amino7,8-benzquinoline
4-amino4-amino-2-methyl2-amino-4-methyl6-amino-2-methyl1'-amino-2-methyl3,4-benzacridine
5-amino
7-amino8-amino8-acetamido8-dimethylamino1,2-benzacridine
5-amino7-amino
8-amino4',5-diaminoCinnoline
3-hydroxy
5-hydroxy
7-hydroxy
4-methoxy

pK

Ref.

9.27, 0.35
7.52, 3.65
8.20, 2.74
4.43
8.75a
9.45a
5.95a
2.5a
8.15a
4.78, 3.73a
4.25, 3.15a
7.68a
7.96a
6.74, 6.02a
5.23a
4.75a
4.70, 4.16a
8.41a
5.03a
7.42 (6.51)a
4.48a
7.31, 6.99
3.45a
8.13a
4.05a
6.72, 5.97a
8.44a
--, 0.21
8.64, 0.21
7.40, 1.92
7.56, 3.31
--, 3.21

39
39
39
6
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
19
39
39
39
39
39

pK

Ref.

4.43
9.16
8.70
8.79
10.80

6
42
42
42
42

11.23

42

pK

Ref.

Heterocyclics
o,o'-dipyridyl
hydantoin
5-isopropyl-2-thio5,5-pentamethylene2-thio
3,5,5-trimethyl-2-thio
3-methyl-5,5-pentamethylene2-thioImidazoles

2-Methylimidazole
7.75
N-Acetylhistidine
7.05
2-Methyl-4-hydroxy-aminobenz- 6.65
4-Hydroxymethyl6.45
2-Methylbenz6.1

43
43
43
43
43

Histamine
4-Hydroxy-6-aminobenz4-Hydroxybenz4-Methoxybenz4-Bromo-

43
43
43
43
43

pK

6.0
5.9
5.3 (OH 9.5)
5.1
3.7

Ref.

6-Nitrobenz4-Nitro-

3.05, 10.6
1.5, 9.1

43
43

isoQuinolines
pK
Ref.
1-Hydroxy-1.2
44
5-Hydroxy
5.40, 8.45
44
3-Amino5.05
40
5-Amino5.59
40
Amino6.20
40
6-Hydroxy5.85, 9.15
44
8-Hydroxy5.66, 8.40
44
2-Methylisoquinolone
-1.8
44
Isoquinoline
5.46, 5.14
44, 19
Phenazine
--, 1.23
39
2-Hydroxy7.5, 2.6
39
10-Methyl-2-phenazone
--, 3.0
6-Aminophenanthridine
6.88
40
9-Aminophenanthridine
7.31
40
o-Phenanthroline
4.27a, 5.2
19
p-Phenanthroline
3.12a
19
1,10-Diamino-3,8-Dimethyl8.78a, 6.31a
Phenanthridine
--, 4.65
44
6-Hydroxy8.43, 5.35
44
9-Hydroxy (phenanthridone) <-1.5
44
a
9-Amino7.31, 6.75
19
2,7,9-Triamino8.06a
19
Phthalazine
3.47
19
1-Amino6.60
19
1-Hydroxy11.00, -2
39
Picolimic acid
5.52
4
5,5-dimethyl-2-thio8.71
42
5,5-Diphenyl-2-thio7.69
42
1-Methyl-5,5-pentamethylene
-2-thio9.25
42
4-Methyl7.45
43
Imidazole
6.95
43
4-(2',4'-Dihydroxyphenyl)6.45
43
Carbobenzoxy-L-histidyl-Ltyrosine ethyl ester
6.25
43
6-Aminobenz6.0 (NH2 3.0)
Benzimidazole
5.4
43
Histidinemethylester
5.2 (NH2 7.1)
43
2-Methyl-4-hydroxy-6-nitrobenzimidazole
3.9
43
4-Hydroxy-6-Nitrobenzb2-Hydroxymethylnaphth(1,2)b2-Hydroxymethylnaphth(2,3)4-Hydroxy1-Amino4-Amino6-Amino8-Amino7-Hydroxy1-Methoxy-

pK

Ref.

3.05

43

4.44, 12.23

86

4.50, 12.23
4.80, 8.68
7.62
6.28
7.17
6.06
5.70
3.05

86
44
40
40
40
40
40
44

27
4-NO2
4-Br
1-Hydroxy5-Methyl-1-phenazone
m-Phenanthroline
1-Amino2,2'-Dipyridyl
2-Hydroxy7-Hydroxy9-Methoxy2-Amino-9-methyl2,7-Diamino-9-methyl6-AminoPhenazine
1-Amino2-Amino1,3-Diamino2,3-Diamino2,7-DiaminoPteroylglutamic acid

Pyridines
2-Amino4-Amino2-Methyl2-Vinyl2-Chloro2,4,6-Trihydroxy1-Methyl-4-pyridone
2-(N-Methylacetamido)2-Benzamido2-(N-Methylbenzamido)3-(N-Methylacetamod)3-(N-Methylbenzamido)4-(N-Methylacetamido)4-(N-Methylbenzamido)4-Benzamido3-NO2
3-COO
2,3-Me2
2,5-Me2
3,4-Me2
2,4,6-Me3
4-OEt

Pyridine
H2 NCONH247
NC-47

2-

6.68b

1.35
3.31
--, 1.44
--, 4.9
3.11a
ca. 7.3, 7.29a
4.23
8.79, 4.82
4.38, 8.68
--, 2.38
5.66a
6.26a
6.88
1.23
2.6a
4.75, 3.46a
5.64a
4.74
4.63, 3.9a
8.26

88
88
39
39
19
19
19
44
44
44
19
19
40
19
19
19
19
19
19
77

pK

Ref.

6.86
9.17
5.94b
4.98
0.49
4,6, 9.0, 13
3.33
2.01
3.33
1.44
3.52
3.66
4.62
4.68
5.32
0.81
4.77
6.60
6.47
6.52
7.48
6.67

41
41
45
45
45
39

3-

5.80b
3.40
1.45

46
46
46
46
46
46
88
47
48
48
48
48
48

4-

8.96b
3.61

Ortho-Substituted Pyridines (in 50% ethanol)

Substituent
pK
Ref.
H2-C2 H52-(CH3)
2,6-[(CH3)2CH]2
2-(CH3)3C-

4.38
4.93
4.68
3.58
4.68

2
2
2
2
2

3-Cl
2.84
3-CO2 Et
3.35
3-COOH
3.13
2-Amyl6.00b
2-Hexyl5.95b
2-Benzyl5.13
2-Bromo0.71
2,4-Dihydroxy
6.50, 13, 1.37
1-Methyl-2-pyridone
0.32
2-Acetamido4.09
1-Methylpyrid-2-one
acetylimine
7.12
3-Acetamido4.46
3-Benzamido3.80
1-Methylpyrid-4-one
acetylimine
11.03
1-Methylpyrid-4-one
benzylimine
9.89
4-COO
4.90
2,4-Me2
6.72
2,6-Me2
6.77
3,5-Me2
6.14
2-Me,5-Et
6.51
3-F
3.10
3-Br
2.84
4-CO2 Et
3.45
aPyridine N-oxides (see oxygen acids)

Substituted Pyridines
Pyridine
2HClICH3CH2(CH3)3CHOSO3-47
CH3OFBrCH3(CH3)2CHCH3CO

5.17b
0.72b
1.82b
5.97b
5.76b
0.75
11.62

3.28
-0.44b
0.90b
5.97b
5.83b

32.84b
3.25b
5.70b
5.82b
4.86
8.72
2.9
4.88
2.97b
2.84b
5.68b
5.72b
3.18b

48
48
88
45
45
45
45
39
39
46
46
46
46
46
46
47
48
48
48
48
48
48
48

4-

6.02b
5.99b
3.27
11.09
6.62
6.02b
6.02b

28
2-C2 H5-6-(CH3)3C4.36
2,6-[(CH3)3C]2
3.58
2-CH35.05
2-(CH3)2CH4.82
2,6-(CH3 )2
5.77
2,6-[(CH3)3C]2
3.58
2-CH3-6-(CH3)3C
5.52
2-(CH3)2CH-6-(CH3)3C5.13
Pyridazine
2.33
3-Hydroxy10.46, -1.8
3,6-Dihydroxy5,67, -2.2, 13
4-Methoxy3.70
3-Amino5.19
4-Hydroxy8.68, 1.07
3-Methoxy2.52
3,6-Dimethoxy1.61
For complex chelating agents, see also ref. 77
b thermodynamic at 25.
Benzimidazole
2-Methyl
2-Ethyl
2-Hydroxymethyl
1-Methyl-2-hydroxymethyl

Other

2
2
2
2
2
2
2
2
19
39
39
39
19
39
39
39

pKNH

6.00
6.96
6.90
-----

Ref. 95

Thiazolidine
Methyl thiazolidine-4-carboxylate
Thiazolidine-4-COOH

5.58
6.29
6.27
5.40
5.55

pK
6.31
4.00
1.51, 6.21

Ref. 96
pK

2-Methyl-2-oxazoline

4-Carbamoyl-2-phenyl-2-oxazoline
2-Phenyl-2-oxazoline

5.5
2.9
4.4

Heterocyclics
Pyrazines

pK

Ref.

Pyrazine
2,5-Dimethyl2,3,5,6-Tetramethyl2-Methoxy2-Methyl2,6-Dimethyl2-Hydroxy1-Methyl-2-pyrazine
2-AminoPyrimidine
2-Amino5-Amino2-Amino-4,6-dimethyl2,4,6-Triamino2-Hydroxy2,4-Dihydroxy-(Uracil)

1.1, 0.6
2.1
2.8
--, 0.75
1.5
2.5
8.23, 0.1
-0.04
3.14
1.30
3.54
2.83
4.85
6.84
9.17, 2.24
9.38, 12

49, 39
49
49
39
49
49
39
39
19
19
19
19
19
19
39
39

35
5.36
6.18
6.14
-----

pKOH
---11.55
11.45

Ref. 86

29
4,6-Dihydroxy5.4
2,4,6-Trihydroxy-(Barbituric
acid)
3.9, 12.5
2-Methoxy<1
4-Methoxy2.5
1-Methyl-2-pyrimidone
2.50
3-Methyl-4-pyrimidone
1.84
4-Amino5.71
2-Amino-4-methyl4.15
2,4-Diamino7.26
4-Methyl1.98
4-Hydroxy8.59, 1.85
4,5-Dihydroxy7.48, 1.99, 11.61
2,4,5-Trihydroxy(isoBarbituric acid)
8.11, 11.48
4-Hydroxy-5-methoxy8.60,1.75
1-Methyl-4-pyrimidone
1.8

Miscellaneous

39
39
39
39
39
39
19
19
19
19
39
39
39
39
39

pK

Ref.

1.74

44

4.34
2.6
-0.17
-0.47
1.87, 6.78
4.08
1.44
4.9

44
44
44
44
44
44
44
44

10-Methyl-2-phenazone
1-Methyl-4-pteridone

3.0
1.25

44
44

Quinoline

2--

HH2 NHO-

4.85*
7.25*
-.36
11.74
5.42
5.8

4.80
4.86*
4.30
8.06
5.14

4.69*
9.08*
2.27
11.25
5.20
5.6

5.37*
5.20
8.54
4.62

5.54*
5.17
8.88
4.92
5.2
4.00*
3.73*
4.98*

6.56*
5.48
8.85
5.08
4.04*

3.90*
5.13
9.89
4.60
5.0
3.08*

4.97*

7.20*

4-Hydroxy-2-methylpyridazinium chloride
8-Hydroxy-6-methyl-1,6naphthyridinium chloride
2-Hydroxyphenazine
4-Hydroxypteridine
3-Methyl-4-pteridone
5-Hydroxypyrimidine
8-Hydroxy-1,6-Naphthyridine
1-Hydroxyphenazine
5-Methyl-1-phenazone

CH3
FClHO2C
NO2

pK

Ref.

2.36*
4.96*

4.62*
1.0388

3.68*
4.53*

Quinoline
pK

Ref.

2,4-Dihydroxy4-Methoxy1-Methyl-4-quinolone
2,4-Diamino-

5.86, 0.76
6.65
2.46
9.45

39
59
39
19

Quinazoline

3.51, 3.2a
pK

19
Ref.

4.81*

Ref.
2
2
44
44
2
2
2
2
2

30
2-Amino6-Amino2-Hydroxy6-Hydroxy3-Methiodide
2-Methoxy2-Methoxy1-Methyl-2-quinolone
4-Amino8-Quinolinol
3-Cl
3-Br
4-Amino8-Amono4-Hydroxy8-Hydroxy2,4-Dihydroxy4-Methoxy*Thermodynamic

Heterocyclics
Quinoxaline
2-Amino-

4.43
3.2a
10.69, 1.30
8.19, 3.12
7.26
1.31
3.17
-0.71
9.44, 9.17
5.13, 9.89
--, 2.46
2.61
5.73
2.4a
9.81, 2.12
8.65, 3.41
9.78, 2.5
3.13

19
19
39
39
39
39
39
39
19, 41
6
88, 44
88
19
19
39
39
39
39

pK

Ref.

0.8, 0.56
3.96

19, 39
19

pK

6-Amino2.95
2-Hydroxy9.08, -1.37
1-Methiodide
5.74
2,3-Dihydroxy9.52
5-Hydroxy-1-methylquioxalinium chloride
5.74
Riboflavin
9.93
Sulphadiazine
6.48
Sulphapyridine
8.43
2-Aminothiazole
5.39
1,3,5-Triazine
-2,4-Dihydroxy6.5
1,4,6-Triazanaphthalene
2.5
4-Hydroxy11.05, 0.78
5-Amino2.62
2,3-Diamino4.70
5-Hydroxy8.65, 0.9
6-Hydroxy7.92, 1.40
1,5-Naphthyridine
2.91
4-Hydroxy
10.01, 2.85
Sulphaquanidine
11.25
Sulphathiazole
7.12
Terramycin
3.10, 7.26, 9.11
Tetramethylenediamine
10.7
1,4,5-Triazanaphthalene
1.20
8-Hydroxy8.76, 0.60

Ref.
19
39
39
39
44
77
6
6
41
39
39
39
39
19
19
39
39
39
39
6
6
77
4
39
39

SPECIAL NITROGEN COMPOUNDS

Hydroxylamines

pK

Ref.

Hydroxylamine

5.97*

12

N-MethylO-MethylTrimethylN-DimethylN,O-Dimethyl-

5.96*
4.60*
3.65*
5.20*
4.75*

12
12
12
12
12

pK

Ref.

8.07
7.87
7.52
6.30
7.71
5.21 (15)
2.38, 7.69
7.21
6.56
7.99

13
13
13
13
13
14
15
13
13
13

7.78
3.24
1.85, 3.54, 10.77

13
15
77

Hydrazines (30)
Hydrazine
MethylN,N'-DimethylTetramethylN,N-DiethylPhenylGlycylhydrazide
N,N-DimethylTrimethylEthylN,N'-DiethylAcetIsonicotinhydrazide

pK

Ref.

Hydrazones Hydrazone of:

Benzophenone
p,p'-Dimethoxyp-Chlorop-Methoxyacetophenone
p,p'-DichloroPhenyl-2-thienyl ketone

pK

Ref.

3.85
4.38
4.38
4.94
3.13
3.80

16
16
16
16
16
16

31
Semicarbazones of:
Semicarbazide
Furfural
Benzaldehyde
Acetone
Acetaldehyde
Pyruvic acid

pK

Ref.

3.66
1.44
0.96
1.33
1.10
0.59

14
14
14
14
14

pK

Ref.

3.02
4.99
5.24
3.11, 5.97
4.03
5.14
~4.77

17
17
17
17
17
17
17

pK

Ref.

4.5
8.30
3.28
8.33
12.52
9.80
5.23
4.57
13.71
10.88
11.6
7.3

6
18
18
19
19
20
18
18
19
19
19
20

Amidoximes
OxBenz-PhenylacetSuccino-Tolup-ToluMalon-

Other
Diphenylthiocarbazone
Phthalimide
Nitrourethane
Acetylguanidine
Acetamidine
O-Methylisourea
Dimedone
Nitrourea
Guanidine
Phenylguanidine
Benzamidine
N-Phenyl-O-methylisourea

Nitrogen compounds, miscellaneous

pK

Diguanide-3.07, 13.25
Dithiooxamide (rubeanic acid,
H2 NCSCSNH2)
10.62
Ethylenediguanide 1.74, 2.88, 11.34, 11.76
Phenyldiguanide
2.16, 10.71

Other

pK

S-Methylisothiourea
9.83
N-Phenyl-S-methylisothiourea 7.14

Ref.
77
77
77

Ref.
20
20

7.73
7.95
9.14
8.50

2
2
2
2

8.44
8.32
9.22
8.81
-0.51
0.18
-0.96

2
2
2
2
4
4
4

pK

Ref.

Thiols
N-Dimethyl-cysteamine
7.95, 10.7
N-Dipropyl-cysteamine
8.00 10.8
N--Mercaptoethylmorpholine
6.65, 9.8
1-Diethylamino-butan- (4)
10.1
Methyl-[-diethylaminoethyl]-sulfide
9.8
Methyl thioglycolate
7.8
Mercaptoethylamine
8.6, 10.75
N-trimethyl cysteine
8.6
Glutathione
2.12, 3.59, 8.75, 9.65
N-Diethyl-cysteamine
7.8, 10.75
N--Mercaptoethyl-piperidine 7.95, 11.05
1-Diethylamino-propan- (3) 8.0, 10.5
1-Diethylamino-hexan- (6)
10.1
p-Nitrobenzenethiol
5.1
Thioglycolic acid
3.67, 10.31
Mercaptoethanol
9.5
Cysteine
1.8, 8.3, 10.8
Cysteinylcysteine
2.65, 7.27, 9.35, 10.85

7
5
5
5
23
23
23
23
5
5
5
5
58
23
23
23
23

X=

-H

-S

-SH

X(CH2 )2SH
X(CH2 )4SH
X(CH2 )3SH
X(CH2 )5SH

12.0
12.4
13.24

13.96
13.25
11.14
13.27

10.75
11.50

77

Cinchona Alkaloids (in 80% aqueous methyl

cellosolve)
pK
Ref.
Quinine
Quinidine
Ephedrine
N-Methylephedrine

Epiquinine
Epiquinidine
-Ephedrine
N-Methyl--ephedrine
Acetamide
Urea
Thiourea

pK

11.82

Ref.

o-Mercapto-phenylacetic acid 4.28, 7.67

59
Ethyl mercaptan
10.50
81
I-Thio-D-sorbitol
9.35
91
2-mercaptoethanesulfonate 7.53 (9.1)
81
o-aminothiophenol
6.59
81
Thiophenol
8.20a, 7.8, 6.52
59, 81, 82
-Mercaptopropionic acid 10.27
81
Methyl cysteine
6.5 (7.5)
81
p-Cl-thiophenol
7.50
81

Mercaptans, RSH
R

pK

Ref.

CH3CCH2 C6H5 CH2HOCH2CH(OH)CH2 CH2=CHCH2 n-C4 H9-

7.86
9.43
9.51
9.96
10.66

32
82
82
82
82

32
t-C5 H11C2H5 OCOCH2 C2H5 OCH2CH2HOCH2CH(OH)CH2 n-C3 H7t-C4 H9-

CARBON ACIDS
Acetone
Acetylacetone
Tricyanomethane
Trinitromethane
Nitromethane

11.21
7.95
9.38
9.66
a10.65
11.05

82
82
82
82
82
82

pK

Ref.

~20
8.95

24
24

pK

Ref.

strong
strong
strong

24
24
25

Diacetylacetone
6
Hydrocyanic acid
9.21
1-nitropropane
9
Saccharin
1.6
Tri-methylsulfonyl-methane strong
Dicyanomethane
12
Acetonitrile
28.9
Benzoylacetone (anol)
8.23
Dimethylsulfone
14
Nitroethane
8.6
2-nitropropane
7.74

Bis-(-Diketones):[(RCO)(R'CO)CH]2CHR (in 50% dioxane)

R
R'
R"
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3

CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3OCH2
CH3OCH2
CH3OCH2
CH3OCH2
CH3OCH2COCH2COCH3
(CH3CO)2 CH(CH2)3CH3

(CH2)5CH3
C6H5
2-ClC6 H4
2-C5 H4 N
2-CH3 OC6 H4
3,4-CH2 O2C6 H3
3-C5 H4 N
4-CH3 OC6 H4
4-(CH3)2 NC6 H4
C6H5
2-C5 H4 N
4-(CH3)2 NC6 H4
4-CH3 OC6 H4

Ref. 28
pK

pK

11.33
11.10
11.04
9.80
11.47
11.39
10.29
11.62
11.50
11.54
10.95
12.13
11.74
9.66
12.07

12.52
12.49
12.73
12.46
12.44
12.60
12.63
12.61
12.45
12.27
12.49
12.31
12.49

Bis-(-Diketones) (RCO)-(R'CO)CH-Y-CH(COR)(COR') (in 50% dioxane)

R
R'
Y
pK
CH3
CH3
CH3
CH3

CH3
CH3
CH3
CH3

(CH2)4
(CH2)10
1,4-(CH3 )2C6 H4

Bis-(-Diketones) RCOCH2 CO-Y-COCH2 COR (in 75% dioxane)

Ref. 26
pK

9.43
11.99
12.01
11.27
Ref. 26

pK

pK

C6H5
C6H5
C6H5
C6H5
C6H5
CH3
CH3=CH(CH3)2

(CH2)4
(CH2)5
(CH2)6
(CH2)7
(CH2)3
(CH2)5
(CH2)5

12.47
12.72
12.60
13.1 (est.)
12.58
12.29
12.95

13.09
13.46
13.46

CH3 NO2
CH3CHClNO2
CH3COCH2 NO2
CH(NO2)3

pK

Ref.

10.29
7
5.1
strong

74
74
74
74

24
25
18
18
24
2
97
24
24
18
18

13.69
13.00
13.60

13.54
12.48
12.07
12.15

33
CH3COCHCl2
CH3COCHC2 H5CO2 C2 H5
CH3COCHCH3 COCH3
CH3COCH2 COC6 H5
C6H5 COCH2 COCF3
CH3COCH2 CHO
CH3 COCH2 CO2CH3
CH3SO2CH2SO2CH3
CH3SO2CH(COCH3)2
C2H5 NO2
C2H5 O2 CCH2 NO2
CH2(NO2)2
CH3COCH2 Cl
CH3COCH2 CO2C2 H5
CH3COCH2 COCH3
CH3COCHBrCOCH3
CH3COCH2 COCF3
C6H5 COCH2 NC5 H5
CH(COCH3)3
CH3SO2CH3
CH(SO2CH3)3
CH2(CN)2
C2H5 O2 CCH2 CN
CH3CO2C2 H5
CHC2 H5(CO2C2 H5)2
CH3CONH2

SOF

15
12.7
11
9.4

74
74
74
74

pK

Ref.

6.82
5.92
10
14
4.3
8.6
5.82
3.57
c. 16.5
10.68
9
7
4.7
10.51
5.85
c. 23
strong
11.81
9
~ 24.5
15
~ 25

74
74
74
74
74
74
74
74
74
74
74
74
74
74
74
74
74
74
74
74
74
74

6.10

74

10.96

74

7.82
4
9.21
strong
13.3
~ 24

74
2
2
74
74
74

10.5

74

10.1

74

CO2Et
O

CH3
O

Dinitromethane
Potassium cyanide
CH(CN)3
CH2(CO2 C2 H5)2
CH3CO2 H
OEt
O

CH3
O

CH2(CHO)2

pK

Ref.

74

pK

Ref.

2.0
4.9
1.65
3.45
3.25
28
4.1
7.3
9.2
2.3
5.0

28
28
28
28
28

Indicators
Tropeoline OO
Bromocresol green
Thymol blue (1)
Methyl orange
Methyl yellow
Neutral red 7.4
Bromophenol blue
Bromothymol blue
Thymol blue (2)
Methyl red (1)
Methyl red (2)

28
28
28
28
28

34
References
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
13.
14.
15.
16.
17.
18.
19.
20.
21.
22.
23.
24.
25.
26.
27.
28.
29.
30.
31.
32.
33.
34.
35.
36.
37.
38.
39.
40.
41.
42.
43.
44.
45.
46.
47.
48.
49.
50.
51.
52.
53.
54.
55.

Hall, H.K., Jr. J. A.m. Chem. Soc. 1957, 79, 5441.

Brown, H.C. et al., in Braude, E.A. and F.C. Nachod Determination of Organic Structures by Physical
Methods, Academic Press, New York, 1955.
Hall, H.K., Jr. J. Am. Chem. Soc. 1957, 79, 5439.
Handbook of Chemistry and Physics, Editor in Chief, Charles D. hodgman, M.S.; Chemical Rubber
Publishing Company, Cleveland, OH, 1951, p. 1636-7.
Franzen, V. Chem. Ber. 1957, 90, 623.
Dawson, R.M.C. et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
Buist, G.J.; Lucas, H.J. J. Am. Chem. Soc. 1957, 79, 6157.
Stevenson, G.W.; Williamson, D. J. Am. Chem. Soc. 1958, 80, 5943.
Soloway, S.; Lipschitz, H. J. Org. Chem. 1958, 23, 613.
Bissell, E.R.; Finger, M. J. Org. Chem. 1959, 24, 1256.
Tuckerman, M.M.; Mayer, J.R.; Nachod, F.C. J. Am. Chem. Soc. 1959, 81, 92.
Bissot, T.C.; Parry, R.W.; Campbell, D.H. J. Am. Chem. Soc. 1957, 79, 796.
Hinman, R.L. J. Org. Chem. 1958, 23, 1587.
Conant, J.B.; Bartlett, P.D. J. Am. Chem. Soc. 1932, 54, 2881.
Lindegren, C.R.; Niemann, C. J. Am. Chem. Soc. 1949, 71, 1504.
Harnsberger, H.F.; Cochran, E.L.; Szmant, H.H. J. Am. Chem. Soc. 1955, 77, 5048.
Pearse, G.A., Jr.; Pflaum, R.T. J. Am. Chem. Soc. 1959, 81, 6505.
Bell, R.P.; Higginson, W.C.E. Pro. Royal Soc. 1949, 197, 141.
Albert, A.; Goldacre, R.; Phillips, J. J. Chem. Soc. 1948, 2240.
Dippy, J.F.J.; Hughes, S.R.C.; Rozanski, A. J. Chem. Soc. 1959, 2492.
Edsall, J.T.; Martin, R.B.; Hollingworth, B.R. PN'As 1958, 44, 505.
Martin, R.B.; Edsall, J.T.; Wetlaufer, D.B.; Hollingworth, B.R. JBC 1958, 233, 1429.
Edsall, J.T.; Wyman and Jeffries, Biophysical Chemistry, Academic Press, Inc., New York, 1958.
Pearson, R.G.; Dillon, R.L. J. Am. Chem. Soc. 1953, 75, 2439.
Ang, K.P. J. Chem. Soc. 1959, 3822.
Martin, D.F.; Fernelius, W.C. J. Am. Chem. Soc. 1959, 81, 1509.
Ellenbogen, E. J. Am. Chem. Soc. 1952, 74, 5198.
Kolthoff, Treatise on Analytical Chemistry, New York, Interscience Encyclopedia, Inc., 1959.
Edwards, J.O. J. Am. Chem. Soc. 1954, 76, 1540.
Bailey, N.A.; Carrington, K.A.; Lott, K.; Symons, M.C.R. J. Chem. Soc. 1960, 290.
Brownstein, S.; Stillman, A.E. J.P.C. 1959, 63, 2061.
Schwarzenbach Helv. Chem. Acta. 1957, 40, 907.
Ingham, J.W.; Morrison, J. J. Chem. Soc. 1933, 1200.
Hildebrand, J.H. Principles of Chemistry, New York, The Macmillan Company, 1940.
Baddiley, in Chargaff, The Nucleic Acids, vol. I, New York, Academic Press, 1955.
Pabst, OR 1.
Bendich, in Chargaff, etc.
Jordan, in Chargaff, etc.
Albert, A.; Phillips, J.N. J. Chem. Soc. 1956, 1294.
Elliott, J.J.; Mason, S.F. J. Chem. Soc. 1959, 2352.
Angyal, S.J.; Angyal, C.L. J. Chem. Soc. 1952, 1461.
Edward, J.T.; Nielsen, S. J. Chem. Soc. 1957, 5075.
Bruice, T.C.; Schmir, G.L. J. Am. Chem. Soc. 1958, 80, 148.
Mason, S.F. J. Chem. Soc. 1958, 674.
Linnell, R.H. J. Org. Chem. 1960, 25, 290.
Jones, R.A.; Katritzky, A.R. J. Chem. Soc. 1959, 1317.
Jaffe, H.H.; Doak, G.O. J. Am. Chem. Soc. 1955, 77, 4441.
Clarke, K.; Rothwell, K. J. Chem. Soc. 1960, 1885.
Keyworth, D.A. J. Org. Chem. 1959, 24, 1355.
Gawron, O.; Duggan, M.; Grelechi, C.J. Anal. Chem. 1952, 24, 969.
Sims, P. J. Chem. Soc. 1959, 3648.
Fickling, M.M.; Fischer, A.; Mann, B.R.; Packer, J.; Vaughan, J. J. Am. Chem. Soc. 1959, 81, 4226.
Wold, F.; Ballou, C.E. JBC 1957, 227, 301.
McElroy, W.D.; Glass, B. Phosphorus Metabolism, Vol. I, Baltimore, Johns Hopkins University Press, 1951.
Kumler, W.D.; Eiler, J.J. J. Am. Chem. Soc. 1943, 65, 2355.

35
56.
57.
58.
59.
60.
61.
62.
63.
64.
65.
66.
67.
68.
69.
70.
71.
72.
73.
74.
75.
76.
77.
78.
79.
80.
81.
82.
83.
84.
85.
86.
87.
88.
89.
90.
91.
92.
93.
94.
95.
96.
97.

VanWazer, J. Phosphorus and Its Compounds, Vol. I, New York, Interscience Encyclopedias, Inc., 1958.
Freedman, L.D.; Doak, G.O. Chem. Rev. 1957, 57, 479.
Ellman, G.L. Arch. Biochem. Biophys. 1958, 74, 443.
Pascal, I.; Tarbell, D.S. J. Am. Chem. Soc. 1957, 79, 6015.
Bascombe, K.N.; Bell, R.P. J. Chem. Soc. 1959, 1096.
Gawron, O.; Draus, F. J. Am. Chem. Soc. 1958, 80, 5392.
Mukherjee, L.M.; Grunwald, E. JPC 1958, 62, 1311.
Ballinger, P.; Long, F.A. J. Am. Chem. Soc. 1959, 81, 1050.
Ballinger, P.; Long, F.A. J. Am. Chem. Soc. 1960, 82, 795.
Haszeldine, R.N. J. Chem. Soc. 1953, 1757.
Deno, N.C.; Berkheimer, H.E.; Evans, W.L.; Peterson, H.J. J. Am. Chem. Soc. 1959, 81, 2344.
Gardner, J.N.; Katritzky, A.R. J. Chem. Soc. 1957, 4375.
Wise, W.M.; Brandt, W.W. J. Am. Chem. Soc. 1955, 77, 1058.
Fortnum, D.H.; Battaglia, C.J.; Cohen, S.R.; Edwards, J.O. J. Am. Chem. Soc. 1960, 82, 778.
Everett, A.J.; Minkoff, G.J. TFS 1953, 49, 410.
Bauer, L.; Miarka, S.V. J. Am. Chem. Soc. 1957, 79, 1983.
Green, A.L.; Sainsbury, G.L.; Saville, B.; Stansfield, M. J. Chem. Soc. 1958, 1583.
Burkhard, R.K.; Sellers, D.E.; DeCou, F.; Lambert, J.L. J. Org. Chem. 1959, 24, 767.
Bell, R.P., The Proton in Chemistry, Ithica, Cornell University Press, 1959.
Stewart, T.D.; Maeser, S. J. Am. Chem. Soc. 1924, 46, 2583.
Jencks, W.P.; Carriuolo, J. J. Am. Chem. Soc. 1960, 82, 1778.
Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
Parsons, R. Handbook of Electrochemical Constants, London, Butterworths, 1959.
Bower, V.E.; Robinson, R.A. JPC 1960, 64, 1078.
Candlin, J.P. J. Chem. Soc. 1960, 4236.
Danehy, J.P.; Noel, C.J. J. Am. Chem. Soc. 1960, 82, 2511.
Kreevoy, M.M. et al. J. Am. Chem. Soc. 1960, 82, 4899.
Kabachnik, M.I., et al. Tetrahedron 1960, 9, 10.
Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
Crutchfield, M.M.; Edwards, J.O. J. Am. Chem. Soc. 1960, 82, 3533.
Lane, T.J.; Quinlan, K.P. J. Am. Chem. Soc. 1960, 2994, 2997.
Moeller, T.; Ferrus, R. JPC 1960, 64, 1083.
Bryson, A. J. Am. Chem. Soc. 1960, 82, 4558, 4862, 4871.
Henderson, W.A., Jr.; Streuli, C.A. J. Am. Chem. Soc. 1960, 82, 5791.
Edwards, J.O. et al. J. Am. Chem. Soc. 1960, 82, 778.
Bell, R.P.; McTigue, P.T. J. Chem. Soc. 1960, 2983.
Li, N.C. et al. J. Am. Chem. Soc. 1960, 82, 3737.
Cohen, W.; Erlanger, B.F. J. Am. Chem. Soc. 1960, 82, 3928.
Olson, D.C.; Margerum, D.W. J. Am. Chem. Soc. 1960, 82, 5602.
Ratner, S.; Clarke, H.T. J. Am. Chem. Soc. 1937, 59, 200.
Porter, G.R.; Rydon, H.N.; Schofield, J.A. Nature 1958, 182, 927.
Richard, J.P.; Williams, G.; Gao, J., J. Am. Chem. Soc., 1999, 121, 715~726.