pKa's of Inorganic and Oxo-Acids

Substrate

pKa H2O (DMSO)

INORGANIC ACIDS
(32)

15.7

H3O+

-1.7

H2S

7.00

HBr

-9.00 (0.9)

HCl

-8.0
3.17

HOCl

7.5

H2O (DMSO)

O
X

(1.8)
(15)

HClO4

-10

HCN

9.4

(12.9)

HN3

4.72

(7.9)

OH

X= CH3
CH2NO2
CH2F
CH2Cl
CH2Br
CH2I
CHCl2
CCl3
CF3
H
HO
C6H5
o-O2NC6H4

4.76 (12.3)
1.68
2.66
2.86
2.86
3.12
1.29
0.65
-0.25
3.77
3.6, 10.3
4.2 (11.1)
2.17

HSCN

4.00

H2SO3

1.9, 7.21

m-O2NC6H4

2.45

H2SO4

-3.0, 1.99

p-O2NC6H4

3.44

o-ClC6H4

2.94

m-ClC6H4

3.83

p-ClC6H4

3.99

HNO3

2.12, 7.21,
12.32
-1.3

HNO2

3.29

H2CrO4

-0.98, 6.50

o-(CH3)3N+C6H4 1.37
p-(CH3)3N+C6H4 3.43

CH3SO3H

-2.6

(1.6)

p-OMeC6H4

CF3SO3H

-14

(0.3)

NH4Cl

9.24

B(OH)3
HOOH

H3PO4

Substrate

CARBOXYLIC ACIDS

H2O

HF

pKa

Substrate

4.47

pKa H2O (DMSO)

ALCOHOLS

Substrate

15.7

(31.2)

MeOH
i-PrOH

15.5

Ph

16.5

(27.9)
(29.3)

t-BuOH

17.0

(29.4)

Ph

c-hex3COH

24.0

CF3CH2OH

12.5

(23.5)

9.3

(18.2)

9.95

(18.0)

(CF3)2CHOH
C6H5OH

8.4

p-O2NC6H4OH

7.1
10.2

2-napthol

Ph

OH

-7.8
OH

Ph

CH3

Ph

O+

Ph

(10.8)
(19.1)

Me

11.6

cis-CO2H

1.92, 6.23

Me

O+ H
H

-2.05

O+

-2.2

OH

OH

11.3 (20.1)

-1.8

Me

Me

Ph
OH

N
O H

OH

N+ OH

8.88 (13.7)
(NH)
(18.5)

0.79

(+1.63)

Me
N

Me

OH

(+5.55)

Me

Me

SULFINIC & SULFONIC ACIDS

O

9.23

-3.8

O+

Me

OH

4.25
3.02, 4.38

-6.5
Me

(17.1)

PEROXIDES

R= H
trans-CO2H

-6.2

O
Ph

-12.4
OH

OH

OXIMES & HYDROXAMIC ACIDS

N

N+

m-O2NC6H4OH
p-OMeC6H4OH

pKa H2O (DMSO)

PROTONATED SPECIES

HOH

O
R

Chem 206

MeOOH

11.5

CH3CO3H

8.2

Me

O
S

OH

-2.6

O
Ph

2.1
OH

*Values <0 for H2O and DMSO, and values >14 for water and >35 for DMSO were extrapolated using various methods.
For a comprehensive compilation of Bordwell pKa data see: http://www.chem.wisc.edu/areas/reich/pkatable/index.htm

pKa Table.1 11/4/05 1:43 PM

D.H. Ripin, D.A. Evans

pKa H2O

Substrate

(DMSO) Substrate

pKa

PROTONATED NITROGEN
N+H4

9.2

EtN+H

10.6

i-Pr2N+H2
Et3N+H
PhN+H3
PhN+(Me)

(10.5)

11.05
10.75 (9.00)

2H

4.6

(3.6)

5.20

(2.50)

Ph2N+H2

0.78

2-napthal-N+H3

4.16

H2NN+H3

8.12

HON+H3

H2O (DMSO)

Quinuclidine

11.0

Me
Me

H2N

(26.5)

AMIDES & CARBAMATES

(9.80)

R= H
(23.5)
CH3 15.1 (25.5)
NH2
Ph
(23.3)
CF3
(17.2)
(urea) NH2
(26.9)
OEt
(24.8)

N+H2 8.36

N-Me morpholine

7.38

NO2
+

O2N

NH3

-9.3

NO2

Et

N+ H

DABCO

2.97, 8.82
(2.97, 8.93)

N+

N
H

6.90, 9.95

+NH
3

+NH

Proton Sponge
PhCN+H

+NH

-9.0, 12.0
(--, 7.50)

(21.6)

Ac2NH

8.30

NH

( )n
O

(20.8)
O

NH

Ph

(17.9)

N
H
NSO2Ph
NH2

H
N

H
N

GUANIDINIUM,
HYRDAZONES,- IDES, & -INES
N+H2
Me2N

(13.6)

NMe2
O

Ph

NNH2
Ph

DBU

(26.1)

(12) (estimate)

N
H
+

N
H

N
H

9.2

NH
HN

R= H (PPTS)
t-Bu
Me
Cl, H

6.95

(19.8)

(13.9)
X= O (24.4)
X= S (27.0)

S
H

(29.4)
Me

NMe
5.21 (3.4)
(0.90)
H
4.95
O
NH
NH
N
(12.1)
N + (18.4)
(4.46)
6.75
H
Me
R
-10
0.72
*Values <0 for H2O and DMSO, and values >14 for water and >35 for DMSO were extrapolated using various methods.

(15)

NH

NH

(18.6)

DMAP
Me2N

N
HN

N
+

(23.0)

NH

X= O (14.8)
X= S (11.8)

(17.2)

PROTONATED HETEROCYCLES

(16.4)

(11.9)

X= O (24)
X X= S (13.3)

N
H
X

PhSO2NHNH2
PhNHNHPh

H
N

Me

(18.9)

(20.95)

(21.6)

NHNH2

(17.3)
(15.0)

R= Me
Ph

HETEROCYCLES

(17.5)
R = Me
Ph
(16.1)
CF3 6.3 (9.7)
MeSO2NHPh
(12.9)
RSO2NH2

n= 1 (24.1)
n= 2 (26.4)

(14.7)

8.88 (13.7)
(NH)

OH

SULFONAMIDE

Bn

NH

NH

H
H3N+

12 (20.5)

Ph

O
NH

pKa H2O (DMSO)

Substrate

HYDROXAMIC ACID & AMIDINES

IMIDES

HN3
4.7 (7.9)
NH3
(41)
38
i-Pr2NH
(36 THF))
26(THF) (30)
TMS2NH
PhNH2 (30.6)
Me
Ph2NH (25.0)
Me
NCNH2 (16.9)
NH (37)
NH (44)

Morpholine

pKa H2O (DMSO)

Substrate

AMINES

5.96
H

N+

Chem 206

pKa's of Nitrogen Acids

N+
Me
Me

(16.5)
i-Pr

N
H

Me

For a comprehensive compilation of Bordwell pKa data see: http://www.chem.wisc.edu/areas/reich/pkatable/index.htm

pKa Table.2 11/4/05 1:43 PM

N+

i-Pr

(24)

D.H. Ripin, D.A. Evans

pKa H2O (DMSO)

Substrate

pKa H2O (DMSO)

Substrate

HYDROCARBONS
O

53

(Me)2CH2

51

CH2=CH2

50

CH4

48
46

(56)

43

(44)

t-BuO

Me

PhH

41

Ph2CH2

33.5 (32.2)

(43)

31.5 (30.6)
24
(28.8)
23

PhCCH
XC6H4CH3
X= p-CN

(30.8)

p-NO2

(20.4)

13

MeO

(15.7)

(20.1)

H2

Et
O

i-Pr

O i-Pr

(20.9)

(26.6)
Ph

Me2N

O
SPh
O
N+Me3

(25.9)
(24.9)

O
CN

(18.2)

(18.0)
Me2N

(17.2)

Me

~36

(25.7)
Me2N

X=

19-20 (27.1)

(28.3)

Me

n=

i-Pr
O

Ph

(26.3)

[30.2 (THF)]

Ph

LiO

t-Bu O
Ph

15

Et

(26.5)
(19.8)
(18.7)
(13.3)
(12.5)

(27.7)

Et2N

20

X= H
Ph
SPh
COCH3
SO2Ph

Me2N

Me

(14.2)

OMe

(26.9)
Me

Me

11

MeO

(26.1)
Me

(20.0)

AMIDES

p-COPh
Me

N+Me3

Me
O

PhCH3

HCCH

(23.6)

EtO

43

Ph3CH

Ph

O
Me

O
EtO

pKa H2O (DMSO)

Substrate

KETONES

24.5 (30.3)

t-BuO

pKa H2O (DMSO)

Substrate

ESTERS

(Me)3CH

CH2=CHCH3

Chem 206

pKa's of CH bonds in Hydrocarbons and Carbonyl Compounds

X= H
CH3
Ph
COCH3
COPh
CN
F
OMe
OPh
SPh
SePh
NPh2
N+Me3
NO2
SO2Ph

(24.7)
(24.4)
(17.7)
(14.2)
(13.3)
(10.2)
(21.6)
(22.85)
(21.1)
(16.9)
(18.6)
(20.3)
(14.6)
(7.7)
(11.4)

H
OMe
NMe2
Br
CN

(24.7)
(25.7)
(27.5)
(23.8)
(22.0)

4
5
6
7
8

(25.1)
(25.8)
(26.4)
(27.7)
(27.4)

(28.1)

(29.0)

(25.5)

(32.4)
Me

Me

Me

*Values <0 for H2O and DMSO, and values >14 for water and >35 for DMSO were extrapolated using various methods.
For a comprehensive compilation of Bordwell pKa data see: http://www.chem.wisc.edu/areas/reich/pkatable/index.htm

pKa Table.3 11/4/05 1:44 PM

pKa's of CH bonds at Nitrile, Heteroaromatic, and Sulfur Substituted Carbon

D.H. Ripin, D.A. Evans

pKa H2O (DMSO)

Substrate

NITRILES
NC

X=

(31.3)
(32.5)
(21.9)
(10.2)

11

(17.1)
(13.1)
(11.1)
(28.1)
(20.6)
(20.8)
(12.0)

MeSCH2SO2Ph

(23.4)

PhSCHPh2

(26.7)

(PhS)3CH

(22.8)

(PrS)3CH

(31.3)

(28.2)

Ph

(26.7)

Ph

(23.0)

N+

Ph

(25.2)

O-

(30.2)

Ph

(30.0)

Ph

(35.1)
(29.0)
(29.0)

Ph

X= H
Ph
SOPh

(33)
(27.2)
(18.2)

Ph

(24.5)

CHPh2

SULFONIUM
Me3S+=O
Ph

S+

(18.2)
(16.3)

CH2Ph

SULFIMIDES & SULFOXIMINES

Ph

Ph
CO2Me
CN
RSCH2CN
R= Me
Et
i-Pr
t-Bu

(30.7)
(20.8)
(19.1)
(24.3)
(24.0)
(23.6)
(22.9)

PhSCH=CHCH2SPh
(26.3)
BuSH
10-11 (17.0)
(10.3)
PhSH
7

Ph
O
Ph
O
Ph
O
Ph

X= H
CH3
t-Bu
Ph
CH=CH2
CH=CHPh
CCH
CCPh
COPh
COMe
OPh
N+Me3
CN
NO2
SMe
SPh
SO2Ph
PPh2
O

Ph

(22.3)
CHPh2
O

(27.6)
(30.7)

Me

(24.5)

CF3
O

(33)

CF3
O

Me
NMe
Me
N+Me2

(14.4)

Me
NTs

CH2Cl

CF3

Et

(31.1)
Me
O

(18.8)
Me
O

(21.8)

i-Pr
O

(26.6)

(20.7)

O
S

(32.8)
Et

(PhSO2)2CH2Me

*Values <0 for H2O and DMSO, and values >14 for water and >35 for DMSO were extrapolated using various methods.

pKa Table.4 11/4/05 1:44 PM

(29.0)
(31.0)
(31.2)
(23.4)
(22.5)
(20.2)
(22.1)
(17.8)
(11.4)
(12.5)
(27.9)
(19.4)
(12.0)
(7.1)
(23.5)
(20.5)
(12.2)
(20.2)

NTs

O
R

R= Me
i-Pr
O

O
S

Ph

NTs

X=

Me

S
N

X= H
Ph
SPh

(30.1)

(PhS)2CHPh

Ph

Me

Me

(30.5)
S
H

SULFONES

(30.8)
(20.8)
(18.7)
(16.9)
(11.8)
(30.8)
(20.5)
(11.0)
(24.9)

Substrate pKa H2O (DMSO)

SULFOXIDES

PhSCH2X
X= Ph
CN
COCH3
COPh
NO2
SPh
SO2Ph
SO2CF3
POPh2

HETERO-AROMATICS

pKa H2O (DMSO)

Substrate

SULFIDES

H
CH3
Ph
COPh
CONR2
CO2Et
CN
OPh
N+Me3
SPh
SO2Ph

pKa H2O (DMSO)

Substrate

Chem 206

(14.3)

D. H. Ripin, D. A. Evans

pKa's of CH bonds at Heteroatom Substituted Carbon & References

pKa H2O (DMSO)

Substrate

ETHERS
CH3OPh
MeOCH2SO2Ph

(30.7)

PhOCH2SO2Ph

(27.9)

PhOCH2CN

(28.1)

(22.85)
Ph

NITRO

P+H4

-14

RNO2

MeP+H3

2.7

Et3P+H
Ph3P+CH3
Ph3P+i-Pr
Ph3P+CH2COPh

9.1
(22.4)
(21.2)
(6.2)

R= CH3
CH2Me
CHMe2
CH2Ph
CH2Bn

Ph3P+CH2CN

(7.0)

PHOSPONATES &
PHOSPHINE OXIDES

SELENIDES
(18.6)
Ph

PhSeCHPh2

(27.5)

(PhSe)2CH2

(31.3)

PhSeCH2Ph

(31.0)

PhSeCH=CHCH2SePh

(27.2)

X=

O
Ph2P

AMMONIUM

X=
Me3N+CH2X
X= CN
SO2Ph
COPh
CO2Et
CONEt2

(20.0)
(24.9)

(17.2)
(16.7)
(16.9)
(12.2)
(16.2)
(11.8)
(7.1)
(7.7)

O2N

Ph

(27.6)

CN
CO2Et

(16.4)

Cl
SiMe3

n=

(18.6)
(26.2)
(28.8)

(26.9)

(17.8)

5
6

(16.0)
(17.9)
(15.8)

SPh
CN

(24.9)
(16.9)

N
Ph

PHOSPHINES
Ph2PCH2PPh2

(29.9)

Ph2PCH2SO2Ph

(20.2)

Ph

JACS 97, 7007 (1975)

JACS 97, 7160 (1975)
JACS 97, 442 (1975)
JACS 105, 6188 (1983)
JOC 41, 1883 (1976)
JOC 41, 1885 (1976)
JOC 41, 2786 (1976)
JOC 41, 2508 (1976)
JOC 42, 1817 (1977)
JOC 42, 321 (1977)
JOC 42, 326 (1977)
JOC 43, 3113 (1978)
JOC 43, 3095 (1978)
JOC 43, 1764 (1978)
JOC 45, 3325 (1980)
JOC 45, 3305 (1980)
JOC 45, 3884 (1980)
JOC 46, 4327 (1981)
JOC 46, 632 (1981)
JOC 47, 3224 (1982)
JOC 47, 2504 (1982)
Acc. Chem. Res. 21, 456 (1988)
Unpublished results of F. Bordwell
Water:

IMINES

(20.6)
(19.4)
(14.6)

10

(EtO)2P

REFERENCES
DMSO:

CH2SPh
CH2SO2Ph
CH2COPh

O
PhSe

pKa H2O (DMSO)

Substrate

PHOSPHONIUM
(49)

MeO

pKa H2O (DMSO)

Substrate

Chem 206

(24.3)

Ph

Oxime ethers are ~ 10 pka units less

acidic than their ketone counterparts
Streitwieser, JOC 1991, 56, 1989

Advanced Org. Chem., 3rd Ed.

J. March (1985)
Unpublished results of W. P. Jencks
THF:
JACS 110, 5705 (1988)
See cited website below for additional
data

*Values <0 for H2O and DMSO, and values >14 for water and >35 for DMSO were extrapolated using various methods.
For a comprehensive compilation of Brodwell pKa data see: http://www.chem.wisc.edu/areas/reich/pkatable/index.htm
pKa Table.5 11/4/05 1:45 PM

DMSO Acidities of Common Heterocycles

Bordwell, ACR, 1988, 21, 456
Bordwell http://www.chem.wisc.edu/areas/reich/pkatable/index.htm
N

N
N
N
H

N
H

23.0

19.8

18.6

16.4

N
H

20.8

24.0

N
H

13.9

11.9

18.0

O
O

N
H

N
H

N
H

O
O

N
H

N
H

N
H

N
H

15.0

12.1

N
H

26.4

24.0
Me

S
S

H
N
H

S
N
H

N
H

Me

S
Me

N+
Me

Me

H
N+

H
Me

N+

Me
Me

13.3

Pka Table.6.cdx 11/4/05 1:45 PM

14.8

11.8

29.4

16.5

18.4

Me

24

Me

pKa Data Compiled by R. Williams

page-1
pKa Values
INDEX

Inorganic

Phenazine

24

Phosphates

Pyridine

25

Carboxylic acids

4, 8

Pyrazine

26

Aliphatic

4, 8

Aromatic

7, 8

Quinoline

27

Phenols

Quinazoline

27

Alcohols and oxygen acids

10, 11

Quinoxaline

27

Amino Acids

12

Special Nitrogen Compounds

28

Peptides

13

Hydroxylamines

28

Nitrogen Compounds

14

Hydrazines

28

Aliphatic amines

15, 17, 19

Semicarbazones

28

Cyanoamines

16

Amidoximes

28

Anilines

17, 18, 20

Thiols

29

Nucleosides

21

Carbon Acids

30,31

Special Table Heterocycles

22

Indicators

31

Acridine

23

References

32-34

Benzoquinoline

24

Cinnoline

23

Hydantoin

24

Imidazole

24

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

pKa Data Compiled by R. Williams

ACIDS

Compound

pK

Ref.

AgOH
Al(OH)3
As(OH)3
H3 AsO 4
H2 AsO 4
HAsO 4 *
As 2 O 3
H3 AsO 3
H3 BO 3
H2 B4 O 7
HB4 O 7
Be(OH) 2
HBr
HOBr
HOCl
HClO2
HClO3
HClO4 (70%)
CH3 SO 3 H
HCN
H2 CO 3
HCO 3
H2 CrO4
HCrO4
HOCN
HZ
H2 GeO3
Ge(OH)4
HI
HOI
HIO3
H4 IO6
H5 IO6
HMnO4
NH3 OH*
NH4 *
HN3
HNO2
HNO3
N2 H5 +
H2 N2 O 2
H2 N2 O 2
H2 OsO 5
H2 O
H3 O +
Pb(OH)2

3.96
11.2
9.22
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
6.48 (10.92)

4
28
28
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
4 (78)

page-2
H3 PO 2
H2 PO 4
HPO 4 _
H3 PO 3
H2 PO 3
H4 P 2 O 7
H3 P 2 O 7
H2 P 2 O 7 =
HP2 O 7 =
HReO4
HSCN
H2 SeO3
HSeO3
H2 SeO4
HSeO4
H3 SiO 3
H2 SO 3
H2 SO 4
HSO 3
HSO 4
H2 S2 O 4
H2 Se
HSe
H2 S
HS
HSbO 2
HTe
H2 Te
H2 TeO 3
Te(OH) 6
H2 VO 4
HVO4 =
H2 CrO4
HOCN
HSCN
H3 PO 2
H3 PO 4
H2 S2 O 3
H3 AuO3
H3 GaO 3
H5 IO6
H4 V6 O 17
H2 NSO 3 H

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!)
1.96
1.0

* Indicates a thermodynamic value.

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

PHOSPHATES AND PHOSPHONATES

Phosphates
Compound

pK

Phosphate
1.97, 6.82, 12.5
Glyceric acid 2-phosphate 3.6, 7.1
Enolpyruvic acid
3.5, 6.4
Methyl1.54, 6.31
Ethyl1.60, 6.62
n-Propyl1.88,6.67
n-Butyl1.80, 6.84
Dimethyl1.29
Di-n-propyl
1.59
Di-n-butyl1.72
Glucose-30.84, 5.67
Glucose-40.84, 5.67
-glycero1.40, 6.44
-glycero1.37, 6.34
3-phosphoglyceric acid
1.42, 3.42
2-phosphoglyceric acid
1.42, 3.55, 7.1
peroxymonophosphoric acid 4.05
diphosphoglyceric acid
7.40, 7.99
glyceraldehyde2.10, 6.75
dioxyacetone1.77,6.45
hexose di1.52, 6.31
fructose-60.97, 6.11
glucose-60.94, 6.11
glucose-11.10, 6.13
adenylic acid
3.8?, 6.2?
inosinic acid
2.4?, 6.4?
ADP
2 strong, 6.6
ATP
3 strong, 6.6
pyrophosphoric acid
0.9, 2.0, 6.6, 9.4
phosphopyruvic acid
3.5, 6.38
creatine phosphate
2.7, 4.5
arginine phosphate
2.8, 4.5, 9.6, 11.2
arginine
2.02, 9.0, 12.5
amino phosphate
(-0.9), 2.8, 8.2
trimetaphosphate
2.05

Ref.
55
53
53
55
55
55
55
55
55
55
56
56
54
54
54
69
54
54
54
54
54
54
54
54
54
54
54
54
54
54
54
54
54
77

Phosphonates
H 2O3P(CH 2) 4PO3H 2 <2, 2.75, 7.54, 8.38
57
H 2O3P(CH 2) 3PO3H 2 <2, 2.65, 7.34, 8.35
57
H 2O3PCH 2CH(CH 3)PO 3H 2 <2, 2.6, 7.00, 9.27 57
H 2O3PCH 2PO3H 2 <2, 2.57, 6.87, 10.33
57
Methyl2.35
57
Ethyl2.43
57
n-propyl2.45
57
isopropyl2.55, 7.75
57
n-butyl2.59, 8.19
57
isobutyl2.70, 8.43
57
s-butyl2.74, 8.48
57
t-butyl2.79, 8.88
57
neopentyl2.84, 8.65
57
1,1 Dimethylpropyl2.88, 8.96
57
n-hexyl2.6, 7.9
57
n-dodecyl--, 8.25
57
CH 3(CH 2) 5CH(COOH)- 1, -57

CF 3CCl 3NH 3+CH 2( OOCCH 2) 2NH +CH 2

CHCl 2CH 2CICH 2Br( OOCCH 22NH +(CH 2) 2CH 2INH 3+CH 2CH 2C6H 5CH=CHHOCH 2C6H 5NH 2+(CH 2) 3C6H 5NH(CH 2) 3Br(CH 2) 2CH 3(CH 2) 5CH(COO)C6H 5CH 2NH 3+(CH 2) 4)NH 3+(CH 2) 5NH 3+(CH 2) 10OOC(CH2) 10(CH 3) 3SiCH 2C6H 5CH 2(C 6H 5)SC-

1.16, 3.93
1.63, 4.81
2.35, 5.9
--, 5.57
1.14, 5.61
1.40, 6.30
1.14, 6.52
--, 6.54
1.30, 6.72
2.45, 7.00
2.00, 7.1
1.91, 7.15
2.1, ---, 7.17
2.25, 7.3
--, 7.5
2.3, 7.55
2.55, 7.55
2.6, 7.6
--, 8.00
--, 8.25
3.22, 8.70
3.3, 8.4
3.85, 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

Arylphosphonic acids
2X-RC6H 3PO3H 2
X
R
Cl
4-O 2N
Br
5-O 2N
Cl
5-Cl
Cl
H
Br
H
Br
5-CH 3
Cl
4-NH 2
CH 3O
4-O 2N
CH 3O
H
CH 3O
4-O 2N
HO
4-O 2N
O2N
H
F
H
I
H
NH 2H
--, 7.29
CH 3H
2.10, 7.68
C6H 5
H
HOOC
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
1.64, 6.80
1.74, 7.06
57
57
(a), 8.13
1.71, 9.17

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

57
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.
triphosphate
tetrametaphosphate

8.90, 6.26, 2.30

2.74

77
77

fluorophosphate
0.55, 4.8
56
Phosphonates (Ref. 2)
X
-H
-H
-NH 3+ -NH 3+
X(CH 2)PO 3H 2
2.35
7.1
1.85
5.35
X(CH 2) 2PO3H 2
2.45
7.85
2.45
7.00
X(CH 2) 4PO3H 2
2.55
7.55
X(CH 2) 5PO3 H2
2.6
7.65
X(CH 2) 6PO2H 2
2.6
7.9
X(CH 2) 10PO2H 2
8.00
Phosphines in acetonitrile, see ref. 89.

CARBOXYLIC ACIDS
Aliphatic
Compound
pK
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
Dethylenediamine- 2.00, 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
Oxaloacetic (trans-enol) 2.56
+(cis-enol)
2.15, 4.06
Protocatechuic
4.48
Pyruvic
2.50
Tartaric +
2.99, 4.40
+ or 2.89, 4.40
meso
3.22, 4.85
Vinylacetic
4.42

Ref.
6
6
6
6
6
6
6
6
2
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6
6

Acetic acids, substituted

H4.76*
O2N1.68*
+
(CH 3)3N 1.83*
+
(CH 3)2NH 1.95*
+
CH 3NH2 2.16*
NH3+2.31*
CH 3SO22.36*
NC2.43*
C 6H5SO22.44
HO2C
2.83*
C 6H5SO2.66
F2.66
Cl2.86*
Br2.86
Cl21.29
F21.24
Br30.66
Cl30.65
F30.23 (-0.26) (2)
HONC4
3.01
F3C3.07*
N33.03
I3.12
C 6H5O3.12
C 2H5O2C3.35
C 6H5S3.52*
CH 3O3.53
NCS3.58
CH 3CO3.58*
C 2H5O3.60
n-C 3H7O
3.65
n-C 4H9O
3.66
sec.-C4H9O3.67
HS3.67*
i-C3H7O3.69*
CH 3S3.72*
i-C3H7S3.72*
C 6H5CH 2S3.73*
C 2H5S3.74*
n-C 3H7S3.77*
n-C 4H9S3.81*
HO3.83*
O3S4.05
(C 6H5)3CS4.30*
C 6H54.31*
CH 2-CH4.35*
* Indicates thermodynamic values.

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
20
20
20
20
20
20
20
20
20
20

Unsaturated acids (25)

Compound
trans-CH 3-CH=CHCO 2H
cis-CH3-CH=CHCO 2H
C 6H5-CH 2CH 2CO2H
trans-C 6H5-CH=CHCO 2H
m-CH 3OC6H4CH 2CH 2CO2H

pK
4.69*
4.44*
4.66*
4.44*

ref.
20
2
2
2
4.65*

2
m-CH 3OC6H4CH=CHCO 2H 4.38*
m-ClC 6H4CH 2CH 2CO2H
4.58*

Compound
H-CH 2CH 2CO2H
H-CH=CHCO 2H
C 6H5CH 2CH 2CO2H
C 6H5CH=CHCO 2H**
C 6H5CH 2CH 2CO2H
C 6H5CH=CHCO 2H**
m-ClC 6H4CH=CHCO 2H**

2
2

pK
4.88*
4.25*
4.66*
4.44*
4.66*
4.44
4.29*

ref.
2
2
2
2
2
2
2

Unsaturated acids, Cis- and TransCis-Acid

H

R2

Trans-Acid
R1

C C
R1

R1

R2

R2
C C

CO 2H

cis-acid

HH4.25*
CH 3H4.44*
ClH3.32
C 6H5H3.88*
ClC 6H4
H3.91
6-BrC 6H4
H4.02
CH 3CH 34.30
C 6H5H5.26***
2,4,6-(CH 3)3C 6H2- H6.12***
C 6H5CH 34.98***
Dicarboxylic acids, unsaturated*
Maleic
1.92, 6.23
2
Citraconic (Dimethylmaleic acid)
2.29, 6.15
2
Acetylenedicarboxylic 1.73, 4.40
2
1
-tetrahydrophthalic
3.01, 5.34
2
Bromomaleic
1.45, 4.62
2
Bromofumaric
1.46, 3.57
2
Chlorofumaric
1.78, 3.81
2
Fumaric
3.02, 4.38
2
Mesaconic (Dimethylfumaric acid)
3.09, 4.75
2
Phthalic
2.95, 5.41
2
Itaconic (1-Propene-2-3-dicarboxylic acid)
3.85, 5.45
2
Chloromaleic
1.72, 3.86
2

CO 2H

trans-acid

Ref.

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

Alicyclic Dicarboxylic acids

cis-Caronic(1,1-dimethylcyclopropane-23dicarboxylic acid
2.34*, 8.31*
2
1,2-trans-cyclopropanedicarboxylic
3.65*, 5.13*
2
trans-caronic
3.82*, 5.32*
2
1,2-cis-cyclopropane-dicarboxylic
3.33*, 6.47*
2
**trans
***in 40% acetone
*thermodynamic

Aliphatic
Alicyclic Dicarboxylic acids
Compound
1,2-trans-Cyclopropanedicarboxylic
trans-Ethyleneoxidedicarboxylic
1,3-trans -Cyclobutanedicarboxylic
1,2-trans-Cyyclopentanedicarboxylic
1,3-trans-Cyclopentanedicarboxylic
1,2-trans-Cyclohexanedicarboxylic
1,3-trans-Cyclohexanedicarboxylic
1,4-trans-Cyclohexanedicarboxylic

pK

Ref

4.31, 5.73

Compound
cis-Ethyleneoxide2
dicarboxylic
1,3-cis-Cyclobutane2
dicarboxylic
1,2-cis-Cyclopentane2
dicarboxylic
1,3-cis-Cyclopentane
2
dicarboxylic
1,2-cisCyclohexane2
dicarboxylic
1,3 -cis-Cyclohexane2
dicarboxylic
1,4-cis-Cyclohexane
2
di-carboxylic

4.18, 5.42

3.65, 5.13
1.93, 3.25
3.81, 5.28
3.89, 5.91
4.40, 5.45
4.18, 5.93

Dicarboxylic acids*
oxalic
1.23,
Malonic
2.83,
Methyl3.05,
Ethyl2.99,
n-propyl
3.00,
i-propyl2.94,
Dimethyl3.17,
Methylethyl2.86, 6.41
Diethyl2.21,
Ethyl-n-propyl2.15,
Di-n-propyl2.07,
Glutaric
4.34,
B-Methyl
4.25,
B-Ethyl
4.29,
B-n-Propyl
4.31,
B,B-Dimethyl3.70,
B,B-Methylethyl3.62,
B,B-Diethyl3.62,
B,B-Di-n-propyl
3.69,
D-Tartaric
3.03,
DL-Tartaric
3.03,
meso-Tartaric
3.29,

4.19
5.69
5.76
5.83
5.84
5.88
6.06
2
7.29
7.43
7.51
5.42
6.22
6.33
6.39
6.29
6.70
7.12
7.31
4.45
---4.92

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

2
Succinic
4.19, 5.48
2
O-O-Dimethyl3.77, 5.94
2
(high melting)
2
O-O-Dimethyl3.94, 6.20
2
(low melting)
2
O,O-Diethyl3.63, 6.46
2
(high melting)
O,O-Diethyl3.51, 6.60
2
2
(low melting)
2
Tetramethyl3.50, 7.28
2
2
2
Adipic
4.42, 5.41
2
Pimelic
4.48, 5.42
2
Suberic
4.52, 5.40
2
Azelaic
4.55, 5.41
2
DL-1:2-Dichlorosuccinic
1.68, 3.18
2
meso-1:2-Dichlorosuccinic 1.74, 3.24
2
DL-1:2-Dibromosuccinic
1.48, ---2
meso-1:2-Dibromosuccinic 1.42, 2.97
20
DL-1:2-Dimethylsuccinic
3.93, 6.00
20
meso-1:2-Dimethylsuccinic 3.77, 5.36
20

2
2
2
2

2
2
2
2
20
20
20
20
20
20

*All are thermodynamic values

Aliphatic
Bicyclo[2.2.2]octane-1-carboxylic acids, 4substituted
HC 2H5O2CNC-

6.75
6.31
5.90

2
2
2

HOBrLysergic acid, etc.

ergometrine
Dihydroergometrine
-dihydrolysergol

6.33
6.08
6.8, -7.4, -8.2, --

2
2
2
2
2

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

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

Hydroxycyclohexanecarboxylic acids
Cyclohexanecarboxylic 4.90
cis-1,2
4.80
cis-1,3
4.60
cis-1,4
4.84
trans-1,2
4.68
trans-1,3
4.82
trans-1,4
4.68

2
2
2
2
2
2
2

Aromatic
benzene-CO3H
Anthracene-1-COOH
Anthracene-9-COOH
naphthalene-2-COOH
Naphthalene-1-COOH

2
2
2
2
2

4.20*
3.69
3.65
4.17
3.69

C 6H5OCH 3(CH 3)2CH(CH 3)3N+NCHO2C*

F3CHOICl(CH 3)3SiC 2H5Oi-C3H7On-C 5H11OC 6H5CH 3CH 2(CH 3)3CHO3PO3SH2N(CH 3)2NHO3AsO2CCH 3NH-

Substituted benzoic acids (ref. 2)

H4.20*
4.21*
O2N2.17*
3.45*
CH 3COCH 3SO23.64*
CH 3SHSBr2.85*
3.81*
F3.27*
3.87*
CH 3O4.09*
4.09*
n-C 3H7O4.24*
4.20*
n-C 4H9O4.25*
Benzene Polycarboxylic acids

3.95*
4.24*

1.37

3.45
3.60*
3.54
3.79
4.08*
3.86*
3.83*
4.24*
4.17*
4.15*

2.95*
2.98*
2.85*
2.94*
4.21*
4.24*
3.46*
3.77
3.46
3.78
4.98
8.42

4.28
4.03
4.15
4.79
5.10

5.41**
5.3

4.60
5.10

4.52*
4.34*
4.35*
3.43
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

*thermodynamic
for complex chelating agents, see also ref. 84.
see also page 9a for more carboxylic acids.

COOH

Benzoic acid

3.53*
3.91*

Ortho-substituted benzoic acids

Benzoic acid
pK
Ref.
2-CH 33.91**
2
2-t-C 4H93.46
2
2,6-(CH 3)23.21
2
2,3,4,6-(CH 3)44.00
2
2,3,5,6-(CH 3)43.52
2
2-C 2H53.77
2
2-C 6H53.46**
2
2,4,6-(CH 3)33.43
2
2,3,4,5-(CH 3)44.22
2

3.44
3.52*
4.00*
4.14*
4.47*
4.46*
4.53*
Ref. 2

Acid

Position of carboxyl pKI

pKII

pKIII

Benzoic
Phthalic
Isophthalic
Terephthalic
Hemimellitic
Trimellitic

1
1,2
1,3
1,4
1,2,3
1,2,4

5.28*
4.46*
4.82*
4.20*
3.84*

5.87*
5.20*

4.17*
2.98*
3.46*
3.51*
2.80*
2.52*

pKIV

pKV

pKVI

8
Trimesic
Mellophanic
Prehnitic
Pyromellitic
Benzenepentacarboxylic
Mellitic
*ionic strength 0.03
**thermodynamic

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
Ref. 77
Aminomalonic acid*
3.32, 9.83
N-Butylaminoacetic acid
2.29, 10.07
2-carboxyethyliminodiacetic acid
2.06, 3.69, 9.66
-carboxymethylaminopropionic
3.61, 9.46
,-diaminobutyric
1.85, 8.24, 10.44
Di-(carboxymethyl)-aminomethyl phosphonic
acid
2.00, 2.25, 5.57, 10.76
,-dimercaptosuccinic
2.40, 3.46, 9.44, 11.82
Ethylenediamine-N,N-diacetic
5.58, 11.05
-hydroxybutyric
3.65
N-2-hydroxyethyliminodiacetic
2.2, 8.73
3-hydroxypropyliminodiacetic
2.06, 9.24
Iminodipropionic
4.11, 9.61
Isobutyric*
4.86
Mandelic acid
3.41
2-Mercaptoethyliminodiacetic
-2.14, 8.17, 10.79
Methyliminodiacetic
2.81, 10.18

3.12*
2.06*
2.38*
1.92*
1.80*
1.40*

3.89*
4.70*
3.25*
4.73*
6.21*
3.51*
4.44*
5.81*
2.87*
4.49*
5.63*
2.73*
3.97*
5.25*
6.46*
2.19*
3.31*
4.78*
5.89* 6.96*
2-Methoxyethyliminodiacetic
2.2, 8.96
2-Methylthioethyliminodiacetic
2.1, 8.91
oxalic acid*
1.25, 4.14
N-n-propylaminoacetic
2.25, 10.03
N-2-sulfoethyliminodiacetic 1.92, 2.28, 8.16
-Bromobutyric acid
2.97
N-(carbamoylmethyl)-imino-diacetic acid
2.30, 6.60
Cyanomethyliminodiacetic
3.06, 4.34
,-diaminopropionic acid
1.23, 6.69
Diethylaminoacetic
2.04, 10.47
Dimethylaminoacetic
2.08, 9.80
N-ethylaminoacetic
2.30, 10.10
Gluconic*
3.86
-hydroxybutyric
4.39
-hydroxypropionic
3.73
Iminodiacetic*
2.98, 9.89
-iodopropionic*
4.04
N-isopropylaminoacetic
2.36, 10.06
-mercaptobutyric
3.53
N-methylaminoacetic
2.24, 10.01
Nitrilotriacetic
3.03, 3.07, 10.
2-Phosphonoethyliminodiacetic
1.95, 2.45, 6.54, 10.46
*Thermodynamic

PHENOLS
Compound
Chromotropic acid
o-Methoxyphenol
o-Hydroxybenzaldehyde
2-Amino-4,5 dimethylphenol hydrochloride
4,5-dihydroxybenzene1,3 disulphonic acid 7.66

pK
5.36, 15.6
--, 9.93

Ref.
6
50

7.95

50

Kojic acid

9.40

Phenol
H(CH 3 ) 3 N+ CH3 SO 2 CH3 COC2 H5 O 2 CC3 H5 CH2 O 2 CBrFHOCH3 CH3 O- O 2 C-- O 3 PC6 H5 2-Chloro-4-Nitro2-Nitro-4-Chloro-

o
9.95*
7.42

* Thermodynamic
**Reference 52

10.4

5.28

51

Compound
pK
Ref.
Resorcinol
--, 9.15 (30 o) 50
p-Methoxyphenol
--, 10.16
3-Hydroxyanthranilic acid
10.09, 5.20
51
2-Aminophenol
hydrochloride
9.99, 4.86
51

50

12.6e
77
m
9.94*
8
9.33
9.19

Phenol
O 2 N8
OCH7.83 NC8.05 CH3 O 2 C8.50* n-C4 H9 O 2 C8.41* I8.42* 9.11* 9.34* Cl8.81* 9.28* 9.95* CH3 S9.48 9.44 9.96 HOCH2 10.28*10.08 10.19* C2 H5 9.93 9.65 10.20 H2 N9.94* 9.39* - O 3 S-- O 3 As
10.2 9.9
9.93 9.59 9.51 NO5.42 79
6.46 79

o
7.23*
6.79

8.48*
9.92*
10.2
9.71

m
p
8.35* 7.14*
8.00 7.66
8.61**7.95
8.47*
8.47*
9.17*
9.02* 9.38*
9.53 9.53
9.83* 9.82*
9.9
10.0
9.87 10.30
9.29 9.03
8.37
6.35**

ALCOHOLS and other OXYGEN ACIDS

Alcohols
Compound
pK
Ref.
Choline
13.9
6
Chloral hydrate
9.66, 11.0
61
Trifluoroethanol
12.5
CF3 CH2 OH
11.4, 12.43
63
CF3 CH(OH)CH3
11.8
63
CF3 CH2 (CH3 )3OH
12.43
10
C3 F7 CH2 OH
11.4**
63
(C3 F7 )2 CHOH
10.6**
63
HCCCH2 OH
13.55
64
C(CH2 OH))4
14.1
64
HOCH2 CHOHCH2 OH
4.4
64
HOCH2 CH2 OH
14.77
64
CH3 CCH2 OH
14.82
64
CH3 OH
15.54
CH2 =CHCH2 OH
15.52
H2 O
15.74
64
CH3 CH2 OH
16
64
Substituent effects for ionization of RCH2OH
R
CCl-3
12.24,11.80
64,65
CF312.37
64
CHF2 CH2 12.74
64
CHCl2 12.89
64
CHEC13.55
64
H2 Cl14.31
64
CH3 CCH2 14.8
64
HOCH2
15.1
H15.5
64
CH2 =CH15.5
64
CH3 -(extrap)
(15.9)
64
CF3 C(CH3 )2 OH
11.6
64
HOCH2 CF2 CH2 OH
11
64
Primary alcohols=RCH2 OH and
Secondary alcohols in 50% alcohol
C2 F5
11.35
65
C4 F9
11.35
65
C5 F11
11.37
65
C7 F15
11.35
65
CHF2
12.00
65
CF2 Cl
11.63
65
CHF2 CF2
11.34
65
CHF2 (CF2 )2
11.35
65
CF3 CH2
12.7
65
CF3 (CH2 )2
12.9
65
CF3 CHMe OH
11.28
65
C3 F7 CHMe OH
11.38
65
C3 F7 CHEt OH
11.37
65
C3 F7 CHPr OH
11.37
65
C3 F7 CH(CF3 ) OH
10.46
65

Compound
pK
C3 F7 CH(C2 F5) OH
10.48
(C3 F7 )2 CHOH
10.52
62
Carbonium ions
Triphenylmethanols in H 2SO 4
4,4,4-Trimethoxy
4,4-Dimethoxy
-1.24
4-Methoxy
-3.40
4-Methyl
-5.41
4 -Trideuteriomethyl5.43
3,3,3-Trimethyl6.35
Unsubstituted triphenylmethanol6.63
64
4,4;,4;-Trichloro64
4 -NitroCCl3 CH2 OH
11.8***
CF3 CH2 OH
11.3***

Hydroxamic acids
FuroGlycine
HippuroisoNicotin
64
p-MethylbenzNicotinNicotin-methiodide
m-NitrobenzPicolin
Pyrimidine-2-carboxSalicylTropo-

Other oxygen acids

Trimethylamine-n-oxide
Dimethylglyoxime
(50% dioxane)
O-methyl ether
Tropolone
-Bromotropolone
Acetald hydrate
Formald hydrate
a 50% dioxane
***50 aquaeous ethanol

Ref.
65
65
HC1O 4 HNO3
.82.
.82
-1.14
-1.11
-3.59
-3.41
-5.67
5.67
-5.95

ref
.80
66
66
66
66
66

-6.89

66
8.01
9.76

8.45
7.40
8.80
7.85
6.46
8.07
8.50
7.88
7.43

6.60
7.749.15-

66
66

72
72
72
72
8.90
8.30

72
72
72
72
72

9.09

4.6

72
72

72

18
12.84

12.92
12a
6.95 a
13.48
13.29

66

77
77
77
77
91
91

OTHER OXYGEN ACIDS

Compound
pK
Ref.
Pyridine oxides
4-Aminopyridine 1-oxide
3.69
67
4-Dimethylaminopyridine 1-oxide
3.88
67
4-Dimethylaminopyridine 1-oxide
3.88
67
4-Dimethylamino-1-methoxypyridinium
perchlorate
>11
67
2-Methylaminopyridine 1-oxide 2.61
67
2-Amino-1-methoxypyridinium perchlorate
12.4
67
4-Hydroxypyridine 1-oxide
2.45
67
4-Methoxypyridine 1-oxide
2.05
67
1-Methoxypyridi-4-one
2.57
67
2-Hydroxypyridine 1-oxide
-0.8
67
2-Ethoxypyridine 1-oxide
1.18
67
1-Methoxypyrid-2-one
-1.3
4-Methylaminopyridine 1-oxide 3.85
67
4-Amino-1-methoxypyridinium perchlorate
>11
67
2-Aminopyridine 1-oxide
2.67
67
2-Dimethylaminopyridine 1-oxide
2.27
67
2-Methylamino-1-methoxypyridinium toluenep-sulphonate
>11
67
4-Benzyloxypyridine 1-oxide 1.99
67
1-Benzyloxypyrid-4-one
2.58
67
2-Methoxypyridine 1-oxide
1.23
67
1-Benzyloxypyrid-2-one
-1.7
67
Pyridine 1-oxides
R
4-CH 3
3-CH 3
3,4-(CH) 4
3-COOC4H9
4-NO2
3-NH2
H
3-COOH
4-COOH

pK
1.29
1.08
1.01
0.03
-1.7
1.47
0.79
0.09
-0.48

Peroxides ROOH (Ref. 70)

H
CH 3
11.6
11.5

Ref.
47
47
47
47
47
47
47
47
47
C 2H5
11.8

Oximes
benzoquinoline mon3-pyridine-1,2-ethanedione-2-oxime
methiodide

Hydroxamic acids
Aceto9.40
n-Butyro9.48
n-Butyro9.00
p-Methoxybenzo9.19
N-Hydroxyphthalimide 7.00, 6.10
Salicylo
7.32
Benzo8.88
p-Chlorobenzo9.59
-Naphtho~7.7
Propiono9.46

Oximes
Benzophenone oxime
11.3
18
Diethyl ketoxime
12.6
18
Isonitrosoacetylacetone (INAA) 7.4
76
5-Methyl-1,2,3-cyclohexanetrione-1,3-dioxime
8.3
76
Acetophenone oxime
11.48
18
Acetoxime
11.42
18
Isonitrosoacetone (INA) 8.3
76
Salicyclaldoxime (SA)
9.2
76
1,2,3-Cyclohexanetrionetrioxime 8.0
76
5-Methyl-1,2,3-cyclohexane-trionetrioxime
8.0
76
Oxygen acids
sulfinic acids
p-Toluenep-Chlorobenzenep-Nitrobenzenep-Bromobenzenem-NitrobenzeneBenzene-

7.20

1.99
73
73
1.89
1.88
1.84, 2.16

Peroxyacids
Peroxymonosulfuric
9.4
Acetic
8.2
n-Butyric
8.2
Formic
7.1
Propionic
8.1
peroxydiphosphoric
5.18, 7.8
peroxymonophosphoric 4.85
iso-C 3H7
12.1

ref. 93
6.25

68
68
68
68
71, 72
68
68
68
68
68

tert-C4H9
12.8

73
73
73
73
69
70
70
70
70
85
90

iso-C 4H9
12.8

Pyridine-2-aldoxime heptiodide
Pyridine-4-aldoxime methiodide
Pyridine-4-aldoxime pentiodide

8.00
8.50
8.50

4-Pyridine-1,2-ethanedione-2-oxime
methiodide
Pyridine-2-aldoxime methiodide
PhenylglyoxaldPyridine-4-aldoxime dodeciodide
Pyridine-3-alkoxime methiodide
Hydroxamic acids
D-LysineN-phenylnicotinoChloroacetoFormop-Chlorophenoxyacetop-Hydroxybenzop-MethoxybenzoN-Phenylbenzoo-AminobenzoL-Tyrosine
L-Lysine
p-Nitrobenzop-AminobenzoL-LactiPropionoPhthaloIndole-3-acetoCyclohexanoHexanoAmino Acids
Compound

7.1
8.0
8.3
8.5
9.2

ref. 93
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
Alanine
2.35
9.69
-Aminobutyric acid 2.55
9.60
-Aminoisobutyric
2.36
10.21
Argininosuccinic >12, 1.62
9.58
2.70, 4.26
Aspartic acid
2.09, 3.86 9.82
Canaline
10.3, 9.20 11.6 (?)
Creatinine
4.84
9.2
Cystine
1.65
7.85
2.26
9.85
Diidotyrosine
6.48, 2.12 7.82
Glutamic acid
2.19, 4.25 9.67
Glycine
2.34
9.6
Histidine
6.0, 1.82
6
Hydroxylsine
2.13
8.62
9.67
Isoleucine
2.36
9.68
Lysine
2.18
8.95
10.53
O-Methyl tyrosine
9.27

Ref.
-NH3
6
6
6
6
6
6
6
6
6
6
6
9.17
6
6
6
21

O-Methyltyrosine ethyl ester 7.31

22
octopine
13, 1.36
8.77
6
2.40
Phenylalanine
1.83
9.13
6
2-Pyrrolidoone-5-carboxylic acid (glucamic
acid)
3.32
Serine
2.21
9.15
6
Threonine
2.63
10.43
6
N-Trimethyl tyrosine
9.75
21
Tyrosine
10.07, 2.20 9.11
Urocanic acid
5.8
3.5
Valine
2.32
9.62
6
-Alanine
3.60
10.19
6
-Aminobutyric acid 4.23
10.43
6
Arginine 12.48
2.17
9.04
6
Asparagine
2.02
8.8
6
Azaserine
8.55
6
Canavanine
7.40, 9.25 11.50 (?) 6
Creatine
2.67
11.02
6
Cysteine 10.78
1.71
8.33
6
3,4-Dihydroxyphenylalanine
9.88, 2.36 8.68
6
11.68
Glutamine
2.17
9.13
6
Histamine 5.0
9.7
6
-Hydroxyglutamic
2.09
9.20
6
acid
4.18
Hydroxyproline
1.92
9.73
6
Leucine
2.36
9.60
6
Methionine
2.28
9.21
1-Methylhistidine
6.48, 1.69 8.85
6
Norleucine
2.39
9.76
6
Norvaline
2.36
9.76
6
Ornithine
1.71
8.69
6
10.76
Proline
1.99
10.60
6
Sarcosine
2.23
10.01
6
Taurine 1.5
8.74
6
Thiolhistidine <1.5, 11.4
1.84
8.47
6
Tryptophan
2.38
9.39
6
Tyrosine ethyl ester 7.33
9.80
22
Peptides
Anserine 7.0
2.65
9.5
6
Carnosine 6.83
-9.51
6
Cystinyldiglycine
3.12
6.36
6
3.12
6.95
Glycylglycine
3.06
8.13
Gly-gly-gly
3.26
7.91
23
Glycylproline
2.84
8.55
6
Aspartyl histi2.45
7.98

dine
Diglycylcystine
Glutathione 9.12

6.82
2.71
2.12
3.53

3.02
7.94
8.66

6
6

Gly-gly-gly-gly
Lysyl-lysine (L,L)

Compound
-COOH
-NH2
-NH2
GlyAla (L) or (D)
3.17
8.23
AlaGly (L) or (D)
3.16
8.24
GlyAlaAla (LL)
3.38
8.10
GlyAlaAla (LD)
3.30
8.17
AlaAlaOH (DD)
3.30
8.14
AlaAlaOH (LD)
3.12
8.30
HAlaAlaAlaOH (3L)
3.39
8.03
HAlaAlaAlaOH (LLD)
3.37
8.05
HAla-Ala-AlaOH (LDL)
3.31
8.13
HAla-Ala-AlaOH (DLL)
3.37
8.06
H-Ala-Ala-AlaOH (3D)
3.39
8.06
HAla-Ala-Ala-AlaOH (4L)
3.42
7.94
HAla-Ala-Ala-AlaOH (LLDL)
3.24
7.93
HAla-Ala-Ala-AlaOH (LDLL)
3.22
7.99
HAla-Ala-Ala-AlaOH (DLLL)
3.42
7.99
HLys-AlaOH (LL)
3.22
7.62
10.70
HLys-AlaOH (LD)
3.00
7.74
10.63
HAla-Lys-AlaOH (3L)
3.15
7.65
10.30
HAla-Lys-AlaOH (LDL)
3.33
7.97
10.36
HAla-Lys-AlaOH (LLD)
3.29
7.84
10.49
HAla-Lys-Ala-AlaOH (4L)
3.58
8.01
10.58
HAla-Lys-AlaOH (LDLL)
3.32
8.01
10.37
HAla-Lys-Ala-Ala-AlaOH (5L)
3.53
7.75
10.35
HAla-Lys-Ala-Ala-AlaOH (LDLLL) 3.30
7.85
10.29
HLys-LysOH (LL)
3.01
7.53
10.05
HLys-LysOH (LD)
2.85
7.53
9.92
HLys-LysOH (3L)
3.08
7.34
9.80
HLys-Lys-LysOH (LDL)
2.91
7.29
9.79
HLys-Lys-LysOH (LDD)
2.94
7.14
9.60
Compound
pK
ref.
Glutathione
3.59, 8.75, 9.65
77
Glycylserine
8.23
77
Glycylleucine
8.13
77
Leucylglycine
7.96
77
Glycylisoleucine
7.96
77
Leucylglycylglycine
7.66
77
Glycylphenylalanine
8.28
77
Glycyltyrosine
8.22
77
Benzylglutamic acid
3.49, 4.99
77
Glycyltryptophane
8.04
77
Glutathione, oxidized
3.15, 4.03, 8.57, 9.54
77
Alanylalanine (LL)
3.30
8.14
92
Alanylalanine (LD)
3.12
8.30
92
Lysylalanine (LL)
3.22
7.62
10.70
92
Lysylalanine (LD)
3.00
7.74
10.63
92
Leucyltyrosine (LL)
3.46
7.84
10.09
92
Leucyltyrosine (DL)
3.12
8.38
10.35
92

3.05
3.01
10.05
-NH2

11.01
10.98
10.54
10.54
10.38

7.75
7.53
11.01

23
6

-NH2 Ref.
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
27
11.32
27
11.42
27
11.09
27

Lysyllysine (LD)
2.85
7.53
NITROGEN COMPOUNDS
Aliphatic Amines
pK
ref.
Ammonia
9.21
1
Primary Amines
-Alanine ester
9.13
1
Allylamine9.69
2
Benzyl
9.34
1
n-Butyl10.59
1
t-Butyl10.55
1
Cyclohexylmethyl10.49
1
Ethanol9.50
1
Ethylenedi9.98, 7.52 1, 77
Hydrazine
8.10
1
Isopropyl10.63
1
Methyl10.62
1
Phenylamyl10.49
2
-Phenylethyl9.83
1
X

XNH 3 +

H9.25*
HF2CRO2CHO5.96*
C 6H54.58*
H2N8.12*
H2C=CHCH 310.64*
X
X-NH3+
X(CH 2)2NH3+
X(CH 2)2NH3+
X(CH 2)4NH3+
X(CH 2)5NH3+
X(CH 2)8NH3+
X(CH 2)10NH3+
X(CH 2)3NH3+

XCH 2 NH 3 +

10.64*
7.52
7.75
9.37*
9.69
10.67*
-H
9.25*
10.64
10.67
10.61
10.63
10.65
10.64
10.58

Secondary amines
DimethylDi-n-propylDiisopropylt-Butylcyclohexyl-Cyclohexylpyrroline
-(p-Tolyl)pyrroline
-Ethylpyrrolidine
-Benzylpyrrolidine
N-methylhydroxylamine
Diethyl-

92
n-Propyl10.53
Trimethylsilymethyl10.96
CH 3ONH2
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
-Phenylpropyl10.20
Triethylenedi8.8*

1
1
12
1
1
1
1
1
1
1
1
1
1
2
1
?

X(CH2 )2 NH 3 + X(CH2 )3 NH 3 + X(CH2 )4 NH 3 +

ref.

10.67*

10.58*

10.61*

X(CH2 )5 NH 3 +

10.63*

9.13
9.50*
9.83*
9.98*

9.71

10.15*

10.37

10.20*
10.65*

10.39*
10.84*

10.49*
11.05*

2
2

10.61*
-CO2

10.64*
-PO3
10.25
10.8
10.8
10.9
11.0

9.77
10.19
10.77
10.75

10.63*
-SO3
1
5.75
9.20
10.65
10.95

11.25

10.43

11.35
10.05

10.58*
-NH3+
-.88

9.31
9.74
10.10
8.59
10.64
11.00
11.05
11.23
7.95
7.59
10.43
10.36
5.96
10.98

9.92

1
1
1
1
2
2
2
2
12
1

Di-n-butyl11.25
Diisobutyl10.50
-Ethylpyrroline
7.43
-Benzylpyrroline7.08
2-Methylpiperidine
10.99
-Cyclohexylpyrrolidine
10.80
-(p-Tolyl)pyrrolidine
10.01
N,O-dimethylhydroxylamine 4.75
Acetanilide
+0.61
*thermodynamic value

1
1
2
2
2
2
2
12
4

Aliphatic Amines
1,2-Iminoethane
7.98
cis-2,3-Iminobutane
8.72
1,2-Imino-2-methylpropane 8.61
1,2-Iminobutane
8.29
trans-2,3-Iminobutane
8.69
Secondary Amines
Allylmethyl10.11
Benzylethyl9.68
Morpholine
8.36
N-Benzoylpiperazine
7.78
Di-sec-butyl11.01
N-Methylmethoxyamine
4.75
Pyrolidine
11.27
1-Tosylpiperazine
7.39
Benzylmethyl9.58
Piperidine
11.22
N-Carbethoxypiperazin
8.28
Dietrimethylsilylmethyl11.40
Diallyl9.29
N-Methylhydroxyl5.96
Trimethyleneimine
11.29
Cis-2,6-dimethyl-piperidine 10.92

Tertiary amines
Trimethyl9.76
Dimethyldiethyl10.29
Dimethyl-n-propyl9.99
Dimethyl-isobutyl9.91
Dimethyl-sec-butyl10.40
Tri-n-propyl10.65
Triallyl8.31
N-Allylpiperidine
9.69
1-Diethylamino-hexane-thiol-(6)
Cyanoamines
N-piperidine-CH2CN
4.55
Et2NCN
-2.0
Et2N(CH 2)2CN
7.65
Et2N(CH 2)4CN
10.08
Et2NC(CH3)2CN
9.13
EtN(CH2CN) 2
-0.6
EtN(CH2CH 2CN) 2
4.55
H2NCH 2CN
5.34
N-Amphetamine-(CH 2)2-CN
7.23
N-Norcodeine-(CH2)2CN
5.68
Dimethylcyanimide
1.2
Diethylcyanimide
1.2
Aminoacetonitrile
5.3
Diethylaminoacetonitrile
4.5

Methyl--diethylamino-ethyl-sulfide
1,2-Dimethyl-2-pyrroline
11.94
2
1-methyl-2-n-butyl-2-pyrroline 11.90
1-Ethyl-2-methyl-2-pyrroline 11.92
2
2
1-n-Butyl-2-methyl- -pyrroline 11.90 2
1,2-Dimethyl-2-tetrahydropyridine
11.57
2
N-Ethyl derivative of: 1,2-Imino-ethane
7.93
7
Trans-2,3-Iminobutane
9.47
7
Trimethylhydroxylamine
3.65
12
Dimethylethyl9.99
1
Triethyl10.65
1
Dimethyl-n-butyl10.02
1
Dimethyl-isopropyl10.30
1
Dimethyl-t-butyl10.52
1
Tri-n-butyl10.89
1
Diallylmethyl8.79
1
1-n-Propylpiperidine
10.48
2
10.1
10.1
5
9.8
-5
1,2-Dimethylpyrrolidine
10.26
2
1-Methyl-2-n-butylpyrrolidin 10.24
2
1-Ethyl-2-methylpyrrolidine
10.64
2
1-n-Butyl-2-methylpyrrolidine 10.43
2
1-Ethyl-2-methylpyrrolidine
10.70
2
1,2-Iminobutane
8.18
7
cis-2,3-Iminobutane
8.56
7
N-dimethylhydroxylamine
5.20
12
Allyldimethyl
8.78
1
1,2-Dimethylpiperidine
10.26
2
2
1-Ethyl-2-methyl- -tetrahydropyridine
11.57
2

7
7
7
7
7
1
1
1
1
1
1
1
1
1
1
1
1
1
1
3

1
1
1
1
1
1
1
2
8
8
8
8
8
8
8
8
8
8
9
9
9
9

2-Amino-2-cyanopropane
5.3
-Isopropylaminopropionitrile 8.0
-Diethylaminopropionitrile
7.6
Et2NCH 2CN
4.55
Et2N(CH 2)3CN
9.29
Et2N(CH 2)5CN
10.46
HN(CH 2CN) 2
0.2
HN(CH 2CH 2CN) 2
5.26
N(CH 2CH 2CN) 3
1.1
N-piperidine-C(CH3)2CN
9.22
N-Methamphetamine-(CH2)2CN 6.95
Methyl cyanamide
1.2
Ethyl cyanamide
1.2
Cyanamide
1.1
Dimethylaminoacetonitrile
4.2

9
9
9
8
8
8
8
8
8
8
8
9
9
9
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
CF 3CH 2NH2
5.7
CF 3CH 2N(CH 3)2
4.75

10
10

CF 3CH 2NHCH 3

6.05

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

10
11
11
11
11
11

R1
R2

CHCH 2NHR4
R3

ref. 11

R1

R2

R3

R4

pK

H
H
H
OH
H
OH
OH
H
H
H
OH
H
OH
OH

H
H
OH
H
OH
OH
OH
H
H
OH
H
OH
OH
OH

H
OH
OH
OH
H
H
OH
H
OH
OH
OH
H
H
OH

H
H
H
H
H
H
H
CH 3
CH 3
CH 2
CH 3
CH 3
CH 3
CH 3

9.78
8.90
8.81
8.67
9.22
8.93
8.58
10.31
9.31
8.62
8.89
9.36
8.78
8.55

Ring amines and imines (in 80% methyl cellosolve) (ref. 2)

Pentamethylene
9.99
Cyclotridecyl
9.63
Hexamethylene
10.00
Cyclotetradecyl
9.54
Heptamethylene
9.77
Cyclopentadecyl
9.54
Octamethylene
9.39
Cycloheptadecyl
9.57
Nonamethylene
9.14
Cyclooctadecyl
9.54
Decamethylene
9.04
Undecamethylene
9.14
Amines other
Dodecamethylene
9.31
Dimeoone
5.23
18
Tridecamethylene
9.35
Phthalimide
8.30
18
Tetradecamethylene
9.35
Nitrourea
4.57
18
Hexadecamethylene
9.29
Nitrourethane
3.28
18
Heptadecamethylene
9.27
Diphenylthiocarbazone
4.5
6
Cyclohexyl
9.82
,,"-Triaminotriethylamine
Cycloheptyl
9.99
8.42, 9.44, 10.13 87
Cyclooctyl
Cyclononyl
9.95
Anilines
Ref. 2
Cyclodecyl
9.85
Monosubstituted
Cycloundecyl
9.71
Substituent
o
m
p
Cyclododecyl
9.62
H4.62*
4.64*
4.58*

(CH 3)3N+CH 3O2CCH 3SO2CH 3SBrFCH 3OC 6H5(CH 3)3CO3SH3N+

O2NHO2CC 2H5O2CF3CHOCl(CH 3)3SiC 2H5OCH 3HO3As
H2N*Thermodynamic
Dimethyl
H
m-NO2
m-CN
p-NO2
p-CN
p-NO

2.16
2.60*
2.96*
4.49*
3.78*
3.78
1.3
-0.28*
2.04
2.10
4.72
2.62*
4.47*
4.38*
3.77
4.47

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

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

5.07
2.63
2.97
0.61
1.78
4.54

Dimethyl (in 50% ethanol)

Substituent XC6H4N(CH3)2
ref. 2
H4.21, 4.09
m-CH 3
4.66
p-C2H54.69
o-(CH 3)2CH5.05
p-CH3CH 2CH 2CH 24.62
o-(CH 3)3C4.26
p-I3.43, 2.73
p-Br3.52, 2.82
p-Cl3.33
m-(CH 3)3Si4.41
o-CH 3O5.49
o-CH 3
5.15, 5.07
p-CH3
4.94
p-CH3CH 2CH 24.43
p-(CH3)2CH4.77
p-(CH3)2CHCH24.19

52
52
52
52
52
52

p-(CH3)3Cm-Brm-Clp-Fp-(CH3)3Sip-CH3O-

4.65
3.08
3.09
4.01
3.99
5.14, 5.16

Ortho-substituted anilines (in 50% ethanol)

H4.25
2-CH 33.98, 4.09
2,3-(CH 3)24.42
2,4-(CH 3)24.61
2,5-(CH 3)24.17, 4.23
2,6-(CH 3)23.42, 3.49
3,5-(CH 3)24.48
2-CH 34.09
2-(CH 3)2CH4.06
2-(CH 3)2C3.38
2,6-(CH 3)2-4-(CH 3)3C- 3.88
2,4-(CH 3)2-6-(CH 3)33.43
2-CH 3-4,6-(CH 3)3C3.31
2,4,6-[(CH 3)3C 3]<2

1-NH2-8-NO21-NH2-8-SO31-NH2-3-SO31-NH2-4-SO31-NH2-5-SO31-NH2-6-SO31-NH2-7-SO31-NH2-8-SO32-NH22-NH2-1-NO22-NH2-3-NO22-NH2-4-NO22-NH2-5-NO22-NH2-6-NO22-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-

Substituted Naphthylamines
1-NH23.92*
1-NH2-2-NO2-1.6
1-NH2-3-NO22.22
1-NH2-4-NO20.54
1-NH2-5-NO22.80
1-NH2-6-NO23.15
1-NH2-7-NO22.83

N-substituted anilines*
R

HCH 3C 2H5n-C 3H7n-C 4H9i-C4H9sec-C4H9t-C 6H12CyclopentylCyclohexylt-C 4H9*Thermodynamic

C 6 H 5 NHR

4.58
4.85
5.11
5.02
4.95
--6.30
5.30
5.60
6.95

C 6 H 5 N(CH 3 )R C 6 H 5 NR 2

4.85
5.06
5.98
--5.20
6.04
-6.71
6.35
7.52

4.58
5.06
6.56
5.59
~5.7
-------

2-CH 3 C 6 H 4 NHR

4.39
4.59
4.92
-----5.07
5.34
6.49

2.79
1.71
3.20*
2.81*
3.69*
3.80*
3.66
5.03*
4.11*
-1.0
2.93
2.63
3.16
2.75
3.13
2.86
2.35
-3.70
3.96*
3.74*
3.95*
3.89*

2-CH 3 C 6 H 4 NR 2

4.39
5.86
7.18

AMINES

ref. 77

Primary amines
2-aminoethylsulphonic acid
9.08
Aminomalonic acid
3.32, 9.83
N-n-butylethylenediamine
7.53, 10.30
2,3-diaminobutane, meso
6.92, 9.97
2,3-diaminobutane, racemic
6.91, 10.00
2,2'-diaminodiethyl sulfide
8.84, 9.64
1,3-diamino-2,2-dimethylpropane 8.18, 10.22
N,N'-Di-(2-aminoethyl)-ethylenediamine
3.32, 6.67, 9.20, 9.92
1,2-diamino-2-methylpropane
6.79, 10.00
1,3-Diaminopropan-2-ol
8.23, 9.68
N,N'-Diglycyethylenediamine
7.63, 8.35
Ethylenediamine-N,N-diacetic acid 5.58, 11.05
Furfurylamine
8.89
2-(2-hydroxypropylamino)-ethylamine 6.94,
9.86
2-(3-hydroxypropylamino)ethylamine
6.78, 9.76
N-Methylaminoacetic acid
2.24, 10.01
Methyl--amino--mercaptoproionate 6.56,
8.99
N-n-propylethylenediamine
7.54, 10.34
1,2,3-triaminopropane
3.72, 7.95, 9.59
Tris-(hydroxymethyl)-aminomethane 8.10
2-amino-2'-hydroxydiethyl sulfide 9.04
N-(carbamoylmethyl)-iminodiacetic acid
2.30, 6.60
2,2'-diaminodiethylamine
3.58, 8.86, 9.65
2,3-diamino-2,3-dimethylbutane 6.56, 10.13
3,3'-diaminodi-n-propylamine
8.02,9.70, 10.7
1,2-Di-(2-aminoethylthio)ethane
8.43, 9.32
1,2-diaminopropane
7.13, 10.00
N,N-diethylethylenediamine
7.07, 10.02
N,N-dimethylethylenediamine
6.63, 9.53
N-Ethylethylenediamine
7.63, 10.56
N-(2-hydroxyethyl)-ethylenediamine
6.83, 9.82
N-isopropylethylenediamine
7.70, 10.62
2-Methoxyethylamine
9.20
Mercaptoethylamine
8.27, 10.53
N-Methylethylenediamine
7.56, 10.40
2-Methylthioethylamine
9.18
2-thienylmethylamine
8.92
Triaminotriethylamine
8.56, 9.59,
10.29

Secondary amines
N-Butylaminoacetic acid
2.29, 10.07
N,N'-Diethylethylenediamine
7.70, 10.46
2,2'-dihydroxydiethylamine
9.00
N,N'-di-n-propylethylenediamine 8.14, 10.97
Ethylenediamine-N,N'-diacetic acid 6.42, 9.46
Iminodipropionic acid
4.11, 9.61
Piperazine
5.68, 9.82
-carboxymethylaminopropionic acid
3.61, 9.46
N,N'-Dimethylethylenediamine
7.40, 10.16
N-ethylaminoacetic acid
2.30, 10.10
Iminodiacetic acid
2.98, 9.89
N-isopropylaminoacetic acid
2.36, 10.06
N-n-propylaminoacetic acid
2.28, 10.03
Tertiary amines
4-(2-aminoethyl)morpholine
4.84, 9.45
Di-(2-hydroxyethyl)aminoacetic acid
8.08
Hexamethylenetetramine
5.13
Methyliminodiacetic acid
2.81, 10.18
Diethylaminoacetic acid
2.04, 10.47
Dimethylaminoacetic acid
2.08, 9.80
N-2-hydroxyethyliminodiacetic acid 2.2, 8.73
Triethylenediamine
4.18, 8.19
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

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

Ref. 5
N-Dimethyl-cysteamine
N-Dipropyl-cysteamine
N--Mercaptoethyl-morpholine
1-Diethylamino-butan- (4)

7.95, 10.7
8.00, 10.8
6.65, 9.8
10.1

Methyl-[-diethylamino-ethyl]sulfide 9.8
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

ANILINES (Ref. 88)

m-Substituted anilines
m-C2 H5
-C(CH3 ) 3
3,5-[C(CH3 ) 3 ] 2
m-CN
3-OCH3 .5-NO2
3,5-Br2
NAPHTHALAMINES

4.70
4.66
4.97
2.76
2.11
2.34

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

4.67
4.74
3.56
3.10
3.82

(reference 88)

substituted naphthalamines
2-naphthalamine
X
1-NH 2 ,3-X
NO2
CN
Cl
Br
I
COOCH 3
OCH 3
OH
CH3
Cl
2-NH 2 ,5-X
NO2
OH
1-NH 2 ,5-X
NO2
OH
Cl
NH2
1-NH 2 ,7-X
NO2
Cl
OCH 3
OH
1-NH 2 ,2-X
NO2
1-X,2-NH2
NO2
1-NH 2 ,8-X
NO2

4.16
2.07
2.26
2.66
2.67

2-naphthalamine
2-NH 2 ,4-X

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

1-NH 2 ,6-X

2-NH 2 ,7-X

2-NH 2 ,6-X
4.07

4.20
-1.74
-0.85
2.79 ,

2-NH 2 ,8-X
1-NH 2 ,4-X
2-NH 2 ,3-X

X
NO2
CN
Cl
Br
I
COOCH 3
OCH 3
NO2
Cl
OCH 3
OH
NO2
Cl
OCH 3
OH
NH2
NO2
OCH 3
NO2
NO2
Br
NO2

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
4.19
4.25
4.66
2.62
4.64
2.73
0.54
3.21
1.48

Anilines (in 50% ethanol)

Unhindered
Aniline
p-Aminodiphenyl
2-Naphthylamine
3-Phenanthrylamine
m-Aminodiphenyl
2-Aminofluorene
2-Phenanthrylamine
2-Anthrylamine
Hindered
o-Aminodiphenyl
peri
1-Naphthylamine
9-Phenanthrylamine
3-Aminopyrene
1-Phenanthrylamine
1-Anthrylamine

pK
4.19
3.81
3.77
3.59
3.82
4.21
3.60
3.40

ref.
40
40
40
40
40
40
40
40

3.03

40

3.40
3.19
2.91
3.23
3.22

40
40
40
40
40

meso
9-Anthrylamine
2.7
o-Aminophenols
3-Hydroxyanthranilic acid
10.09, 5.20
2-Aminophenol hydrochloride
9.99, 4.86
Indicators
p-Aminoazobenzene
2.82, 2.76
4-Chloro-2-nitroaniline
-1.02, -1.03
4,6-Dichloro-2-nitroaniline
-3.61, -3.32
6-Bromo-2,4-dinitroaniline
-6.64, -6.71
2-Amino-4,5-dimethylphenol hydrochloride
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

Heterocyclics
Nucleosides, etc.
Adenine
2'-AMP
3'-AMP
ADP
ATP
Barbital
Cytosine
Cytosine (deoxy)
3' CMP
CDP
CDP, (deoxy)
Guanine
Guanosine
"
5'-GMP
GDP
Hypoxanthine

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

40
51
51
60
60
60
10.40,
51
60
60
60

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

5'-IMP
8.9, 1.54, 6.04
6
5-Methylcytosine
4.6, 12.4
6
5-Methylcytosine deoxyriboside 5'-phosphate
4.4
6
3-Methyluracil
9.75
37
3-Methylxanthine
8.5 (8.1), 11.3
38
Adenosine
3.63
6
"
3.3, 12.5
35
5'-AMP
3.3, 6.1
36
3.74, 6.2-6.4
6
Barbituric acid
3.9, 12.5
37
Cytidine
4.11
6
"
4.22, 12.5
35
2'-CMP
4.3-4.4, 6.19*
6
5'-CMP
4.5, 6.3
6
CTP
4.6, 6.4
6
2,6-Diaminopurine
5.09, 10.77
6
Isoguanine
4.51, 8.99
6
Guanosine (deoxy)
1.6-2.2, 9.16-9.5 6
GMP (2' + 3')
2.3, 9.36, 0.7, 5.9 6
5'-GMP (deoxy)
2.9, 9.7, 6.4
6
GTP
3.3, 9.3, 6.5
6
Inosine
1.2, 8.9
6
"
8.75, 12.5
6
5-Methylcytosine deoxyriboside
4.5, 13.0
6
1-Methyluracil
9.95
37
1-Methylxanthine
7.7, 12.05
38
7-Methylxanthine
8.5 (8.3)
38
9-Methylxanthine
6.3
38
Purine
2.52, 8.90
37
Thymidine
9.8
6
5'-TMP
10.0, 1.6, 6.5
6
Uracil deoxyriboside 9.3
6
5'-UMP
9.5, 6.4
6
UTP
9.5, 6.6
6
Uridine
9.25
6
"
9.17, 12.5
35
Xanthosine
0, 5.5, 13.0
6
Orotic acid
2.8, 9.45, 13
6
Pyrimidine
1.30
37
Thymine
0, 9.9, 713.0
6
Uracil
.5, 9.5, 13.0
6
UMP (2' + 3')
9.43, 1.02, 5.88 6
UDP
9.4, 6.5
6
Uric acid
5.4, 10.3
6
Xanthine
0.8, 7.44, 11.12 6
"
7.2
38

Heterocyclic Bases (Ref. 2)

5

6
7

Isoquinoline 5.14*

Pyridine 5.14*
pK (20)

Benzoquinoline 5.05*

Quinoline 4.85*

N
9

10

Phenanthridine 3.30a

7,8-Benzoquinoline
4.25*

5,6-Benzoquinoline
5.15*

Acridine 5.60

2,3-Benzacridine 4.52a

3,4-Benzacridine 4.70*

1,2-Benzacridine 3.45a
N

N
N

N
Pyrazine 0.37*

Pyrimidine 1.10*

Pyridazine 2.10*

N
N

N
N
Quinazoline 3.31*

Phthalazine 3.39*

Cinnoline 2.64*

N
Quinoxaline 0.6*

50% EtOH

Heterocyclics
Aureomycin
Iridine

Acridine

1--

3.30, 7.44, 9.27

--, 5.62

77
39

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

2--

3--

4--

5--

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

9--

Ref. 2

39
39
39

H-H2N-HO-CH 3-H2K-(1-CH 3--)-1,9-(CH 3)2--

5.60*
4.40*
3.59a
4.18a
10.7a
3.95a

4.11a
8.04*
7.61a
4.86a
9.9a

5.88*
5.03a
5.5239
8.8139
4.60a

6.04*
5.50a
4.45a
9.4*
4.79a

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

3.22a

2.88a

50% ethanol; ref. 39

8-amino-1,2-benzacridine 6.72
2-amino-4-methyl-5,6-benzoquinoline
40
3-amino-6,7-benzoquinoline 4.78
8-amino-3,4-benzacridine 7.42
1'-amino-5,6-benzoquinoline 5.03
4'-amino-5,6-benzoquinoline 5.20
2-amino-4-methyl-7,8,benzoquinoline
6.74
6,7-benzoquinoline
5.05, 3.84a
5,6-benzoquinoline
5.15, 3.90a
4-amino7.99a
2-methyl4.44a
4-amino-2-methyl8.45a
2-amino-4-methyl7.14, 6.51a
4'-amino5.20, 4.10a
3'-amino4.02a
1'-amino5.03
2',4'-diamino4.91a
Benziminazole
5.53
2-amino7.54
Benztriazole
1.6
Benzthiazole
1.2, 0.1a
2-amino4.51
benzoxazole
(decomp.)
2-amino3.73
2,3-benzacridine
4.52a
5-amino9.72a
5-acetamido4.56a
7-amino5.38a
5-amino-6:7:8:9-tetrahydro- 9.66a
Caffeine
0.61
cinchonine
7.2
Cinnoline
2.70
4-amino6.84
Cocaine
7.6
Cinnoline 4-hydroxy
9.27, 0.35
6-hydroxy
7.52, 3.65
-hydroxy
8.20, 2.74

40
7.14
40
40
40
40
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
39
39
39

,'-dipyridyl
4.43
4-amino8.75a
4-amino-2-methyl9.45a
4-amino-2-methyl-8-chloro- 5.95a
8-chloro2.5a
3,4-diamino8.15a
3-amino4.78, 3.73a
7,8-benzquinoline
4.25, 3.15a
4-amino7.68a
4-amino-2-methyl7.96a
2-amino-4-methyl6.74, 6.02a
6-amino-2-methyl5.23a
1'-amino-2-methyl4.75a
3,4-benzacridine
4.70, 4.16a
5-amino
8.41a
7-amino5.03a
8-amino7.42 (6.51)a
8-acetamido4.48a
8-dimethylamino7.31, 6.99
1,2-benzacridine
3.45a
5-amino8.13a
7-amino
4.05a
8-amino6.72, 5.97a
4',5-diamino8.44a
Cinnoline
--, 0.21
3-hydroxy
8.64, 0.21
5-hydroxy
7.40, 1.92
7-hydroxy
7.56, 3.31
4-methoxy
--, 3.21
Heterocyclics
o,o'-dipyridyl
4.43
hydantoin
9.16
5-isopropyl-2-thio8.70
5,5-pentamethylene2-thio 8.79
3,5,5-trimethyl-2-thio
10.80
3-methyl-5,5-pentamethylene-2-thio11.23
Imidazoles

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
6
42
42
42
42
42

2-Methylimidazole
7.75
43
N-Acetylhistidine
7.05
43
2-Methyl-4-hydroxy-aminobenz- 6.65 43
4-Hydroxymethyl6.45
43
2-Methylbenz6.1
43
Histamine
6.0
43
4-Hydroxy-6-aminobenz- 5.9
43
4-Hydroxybenz5.3 (OH 9.5)43
4-Methoxybenz5.1
43
4-Bromo3.7
43
6-Nitrobenz3.05, 10.6 43
4-Nitro1.5, 9.1
43
isoQuinolines
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
a
o-Phenanthroline
4.27 , 5.2 19
p-Phenanthroline
3.12a
19
a
a
1,10-Diamino-3,8-Dimethyl- 8.78 , 6.31
Phenanthridine
--, 4.65
44
6-Hydroxy8.43, 5.35 44
9-Hydroxy (phenanthridone) <-1.5
44
9-Amino7.31, 6.75a 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-pentamethyl-ene-2-thio9.25
42
4-Methyl7.45
43
Imidazole
6.95
43
4-(2',4'-Dihydroxyphenyl)- 6.45
43
Carbobenzoxy-L-histidyl-L-tyrosine ethyl
ester
6.25
43
6-Aminobenz6.0 (NH2 3.0)
Benzimidazole
5.4
43

Histidine

methylester
5.2 (NH2 7.1)
43
2-Methyl-4-hydroxy-6-nitro-benzimidazole
3.9
43
4-Hydroxy-6-Nitrobenz3.05
43
b2-Hydroxymethylnaphth(1,2)4.44, 12.23 86
b2-Hydroxymethylnaphth(2,3)4.50, 12.23 86
4-Hydroxy4.80, 8.68 44
1-Amino7.62
40
4-Amino6.28
40
6-Amino7.17
40
8-Amino6.06
40
7-Hydroxy5.70
40
1-Methoxy3.05
44
4-NO2
1.35
88
4-Br
3.31
88
1-Hydroxy--, 1.44
39
5-Methyl-1-phenazone
--, 4.9
39
m-Phenanthroline
3.11a
19
a
1-Aminoca. 7.3, 7.29 19
2,2'-Dipyridyl
4.23
19
2-Hydroxy8.79, 4.82 44
7-Hydroxy4.38, 8.68 44
9-Methoxy--, 2.38
44
2-Amino-9-methyl5.66a
19
a
2,7-Diamino-9-methyl6.26
19
6-Amino6.88
40
Phenazine
1.23
19
a
1-Amino2.6
19
2-Amino4.75, 3.46a 19
1,3-Diamino5.64a
19
2,3-Diamino4.74
19
a
2,7-Diamino4.63, 3.9
19
Pteroylglutamic acid
8.26
77
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)-

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

41
41
45
45
45
39
46
46
46
46

4-(N-Methylbenzamido)4.68
4-Benzamido5.32
3-NO2
0.81

3-COO
4.77
2,3-Me2
6.60
2,5-Me2
6.47
3,4-Me2
6.52
2,4,6-Me3
7.48
4-OEt
6.67
3-Cl
2.84
3-CO2Et
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-CO2Et
3.45
Pyridine N-oxides (see oxygen acids)
Substituted Pyridines
Pyridine
2H5.17b
Cl0.72b
I1.82b
CH 3CH 25.97b
(CH 3)3C5.76b
HO0.75
11.62
-47
SO3
CH 3O3.28
F-0.44b
Br0.90b
CH 35.97b

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

46
46
88
47
48
48
48
48
48
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

(CH 3)2CHCH 3CO

H2NCONH247
NC- 47

5.83b
6.68b

5.72b
3.18b
5.80b
3.40
1.45

6.02b
8.96b
3.61

Ortho-Substituted Pyridines (in 50% ethanol)

Substituent
pK
ref.
H4.38
2
2-C 2H54.93
2
2-(CH 3)
4.68
2
2,6-[(CH 3)2CH] 2
3.58
2
2-(CH 3)3C4.68
2
2-C 2H5-6-(CH 3)3C4.36
2
2,6-[(CH 3)3C] 2
3.58
2
2-CH 35.05
2
2-(CH 3)2CH4.82
2
2,6-(CH 3)2
5.77
2
2,6-[(CH 3)3C] 2
3.58
2
2-CH 3-6-(CH 3)3C
5.52
2
2-(CH 3)2CH-6-(CH3)3C5.13
2
Benzimidazole
2-Methyl
2-Ethyl
2-Hydroxymethyl
1-Methyl-2-hydroxymethyl

6.31
4.00
1.51, 6.21

(ref. 96)
2-Methyl-2-oxazoline
4-Carbamoyl-2-phenyl-2-oxazoline
2-Phenyl-2-oxazoline
Heterocyclics
Pyrazines
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-Hydroxy-

pK
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

5.5
2.9
4.4
ref.
49, 39
49
49
39
49
49
39
39
19
19
19
19
19
19
39

2.33
10.46, -1.8
5,67, -2.2, 13
3.70
5.19
8.68, 1.07
2.52
1.61

19
39
39
39
19
39
39
39

For complex chelating agents, see also ref. 77

b thermodynamic at 25.

pKNH
5.58
6.29
6.27
5.40
5.55

6.00
6.96
6.90
-----

Other
(ref. 95)
Thiazolidine
Methyl thiazolidine-4-carboxylate
Thiazolidine-4-COOH

Pyridazine
3-Hydroxy3,6-Dihydroxy4-Methoxy3-Amino4-Hydroxy3-Methoxy3,6-Dimethoxy-

35
pKOH
5.36
6.18
--6.14
---11.55
ref. 86
--11.45
2,4-Dihydroxy-(Uracil)
9.38, 12
39
4,6-Dihydroxy5.4
39
2,4,6-Trihydroxy-(Barbituric acid)
3.9, 12.5
39
2-Methoxy<1
39
4-Methoxy2.5
39
1-Methyl-2-pyrimidone
2.50
39
3-Methyl-4-pyrimidone
1.84
39
4-Amino5.71
19
2-Amino-4-methyl4.15
19
2,4-Diamino7.26
19
4-Methyl1.98
19
4-Hydroxy8.59, 1.85 39
4,5-Dihydroxy7.48, 1.99, 11.61 39
2,4,5-Trihydroxy-(isoBarbituric acid)
8.11, 11.48 39
4-Hydroxy-5-methoxy8.60
1.75
39
1-Methyl-4-pyrimidone
1.8
39
Miscellaneous
4-Hydroxy-2-methylpyridazinium chloride
1.74
44
8-Hydroxy-6-methyl-1,6-naphthyridinium
chloride
4.34
44
2-Hydroxyphenazine
2.6
44
4-Hydroxypteridine
-0.17
44
3-Methyl-4-pteridone
-0.47
44
5-Hydroxypyrimidine
1.87, 6.78 44
8-Hydroxy-1,6-Naphthyridine 4.08
44
1-Hydroxyphenazine
1.44
44

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

4.9
3.0
1.25

Quinoline
HH2NHO-

3
4.80
4.86*
4.30
8.06
5.14

CH 3
FClHO2C
NO2

2-4.85*
7.25*
-.36
11.74
5.42
5.8

4
4.69*
9.08*
2.27
11.25
5.20
5.6

2.36*
4.96*

Quinoline
2,4-Dihydroxy4-Methoxy1-Methyl-4-quinolone
2,4-DiaminoQuinazoline
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-Amino6-Amino2-Hydroxy1-Methiodide
2,3-Dihydroxy-

44
44
44

4.62*
1.0388

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*

3.68*
4.53*

5.86, 0.76
6.65
2.46
9.45
3.51, 3.2a
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

0.8, 0.56
3.96
2.95
9.08, -1.37
5.74
9.52

39
59
39
19
19
19
19
39
39
39
39
39
39
19, 41
6
88, 44
88
19
19
39
39
39
39

19, 39
19
19
39
39
39

4.81*

Ref.
2
2
44
44
2
2
2
2
2

5-Hydroxy-1-methylquioxalinium chloride
5.74
44
Riboflavin
9.93
77
Sulphadiazine
6.48
6
Sulphapyridine
8.43
6
2-Aminothiazole
5.39
41
1,3,5-Triazine
-39
2,4-Dihydroxy6.5
39
1,4,6-Triazanaphthalene
2.5
39
4-Hydroxy11.05, 0.78 39
5-Amino2.62
19
2,3-Diamino4.70
19
5-Hydroxy8.65, 0.9
39
6-Hydroxy7.92, 1.40 39
1,5-Naphthyridine
2.91
39
4-Hydroxy
10.01, 2.85 39
Sulphaquanidine
11.25
6
Sulphathiazole
7.12
6
Terramycin
3.10, 7.26, 9.11
77
Tetramethylenediamine
10.7
4
1,4,5-Triazanaphthalene
1.20
39
8-Hydroxy8.76, 0.60 39
SPECIAL NITROGEN COMPOUNDS
Hydroxylamines
Hydroxylamine
N-MethylO-MethylTrimethylN-DimethylN,O-Dimethyl-

5.97*
5.96*
4.60*
3.65*
5.20*
4.75*

12
12
12
12
12
12

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

8.07
7.87
7.52
6.30
7.71
5.21 (15)
2.38, 7.69
7.21
6.56
7.99
7.78
3.24
1.85, 3.54, 10.77
77

13
13
13
13
13
14
15
13
13
13
13
15

Hydrazones Hydrazone of:

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

3.85
4.38
4.38
4.94
3.13
3.80

16
16
16
16
16
16

Semicarbazones of:
Semicarbazide
Furfural
Benzaldehyde
Acetone
Acetaldehyde
Pyruvic acid

3.66
1.44
0.96
1.33
1.10
0.59

14
14
14
14
14

Amidoximes
OxBenz-PhenylacetSuccino-Tolup-ToluMalon-

3.02
4.99
5.24
3.11, 5.97
4.03
5.14
~4.77

17
17
17
17
17
17
17

Other
Diphenylthiocarbazone
Phthalimide
Nitrourethane
Acetylguanidine
Acetamidine
O-Methylisourea
Dimedone
Nitrourea
Guanidine

4.5
8.30
3.28
8.33
12.52
9.80
5.23
4.57
13.71

6
18
18
19
19
20
18
18
19

Phenylguanidine
10.88
Benzamidine
11.6
N-Phenyl-O-methylisourea 7.3
Nitrogen compounds, miscellaneous
Diguanide-3.07, 13.25
Dithiooxamide (rubeanic acid,
H2NCSCSNH 2)
10.62
Ethylenediguanide
1.74, 2.88, 11.34, 11.76
Phenyldiguanide
2.16, 10.71
Other
S-Methylisothiourea
9.83
N-Phenyl-S-methylisothiourea 7.14

19
19
20

77
77
77
77

20
20

Cinchona Alkaloids (in 80% aqueous

cellosolve)
Quinine
7.73
Quinidine
7.95
Ephedrine
9.14
N-Methylephedrine
8.50
Epiquinine
8.44
Epiquinidine
8.32
-Ephedrine
9.22
N-Methyl--ephedrine
8.81

methyl

Acetamide
Urea
Thiourea

4
4
4

-0.51
0.18
-0.96

2
2
2
2
2
2
2
2

Thiols
N-Dimethyl-cysteamine
7.95, 10.7 7
N-Dipropyl-cysteamine
8.00 10.8
5
N--Mercaptoethyl-morpholine 6.65, 9.8
1-Diethylamino-butan- (4) 10.1
5
Methyl-[-diethylamino-ethyl]-sulfide 9.8
5
Methyl thioglycolate
7.8
23
Mercaptoethylamine
8.6, 10.75 23
N-trimethyl cysteine
8.6
23
Glutathione
2.12, 3.59, 8.75, 9.65 23
N-Diethyl-cysteamine
7.8, 10.75 5
N--Mercaptoethyl-piperidine
7.95, 11.05 5
1-Diethylamino-propan- (3) 8.0, 10.5
5
1-Diethylamino-hexan- (6) 10.1
5

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
X=
X(CH 2)2SH
X(CH 2)4SH
X(CH 2)3SH
X(CH 2)5SH

-H
12.0
12.4
13.24

-S
13.96
13.25
11.14
13.27

58
23
23
23
23
-SH
10.75
11.50
11.82

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
a
Thiophenol
8.20 , 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
CH 3CCH 2C 6H5CH 2HOCH2CH(OH)CH 2CH 2=CHCH 2n-C 4H9t-C 5H11C 2H5OCOCH2C 2H5OCH2CH 2HOCH2CH(OH)CH 2n-C 3H7t-C 4H9-

7.86
9.43
9.51
9.96
10.66
11.21
7.95
9.38
9.66
a10.65
11.05

32
82
82
82
82
82
82
82
82
82
82

CARBON ACIDS
Acetone
~20
Acetylacetone
8.95
Diacetylacetone
6
Hydrocyanic acid
9.21
1-nitropropane
9
Saccharin
1.6
Tri-methylsulfonyl-methane strong

Dicyanomethane
Acetonitrile
Benzoylacetone (anol)
Dimethylsulfone
Nitroethane
2-nitropropane
Tricyanomethane
Trinitromethane
Nitromethane

24
24
24
25
18
18
24

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

R
R'
R"
CH 3
CH 3
(CH 2)5CH 3
CH 3
CH 3
C 6H5
CH 3
CH 3
2-ClC 6H4
CH 3
CH 3
2-C 5H4N
CH 3
CH 3
2-CH 3OC6H4
CH 3
CH 3
3,4-CH 2O2C 6H3
CH 3
CH 3
3-C 5H4N
CH 3
CH 3
4-CH 3OC6H4
CH 3
CH 3
4-(CH 3)2NC 6H4
CH 3
CH 3OCH2
C 6H5
CH 3
CH 3OCH2
2-C 5H4N
CH 3
CH 3OCH2
4-(CH 3)2NC 6H4
CH 3
CH 3OCH2
4-CH 3OC6H4
CH 3OCH2COCH 2COCH 3
(CH 3CO)2CH(CH2)3CH 3

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
c. 25
8.23
14
8.6
7.74
strong
strong
strong

2
24
24
24
18
18
24
24
25
(ref. 28)
pK
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)

(ref. 26)

R
CH 3
CH 3
CH 3
CH 3

pK
13.54
12.48
12.07
12.15

R'
CH 3
CH 3
CH 3
CH 3

Y
(CH 2)4
(CH 2)10
1,4-(CH 3)2C 6H4

Bis-( -Diketones) RCOCH 2CO-Y-COCH2COR (in 75% dioxane)

R
Y
pK
C 6H5
(CH 2)4
12.47
C 6H5
(CH 2)5
12.72
C 6H5
(CH 2)6
12.60
C 6H5
(CH 2)7
13.1 (est.)
C 6H5
(CH 2)3
12.58
CH 3
(CH 2)5
12.29
CH 3=CH(CH 3)2 (CH 2)5
12.95

pK
9.43
11.99
12.01
11.27

(ref. 26)
pK
13.09
13.46
13.46
13.69
13.00
13.60

CH 3NO2
CH 3CHClNO2
CH 3COCH 2 NO2
CH(NO2)3
CH 3COCHCl 2
CH 3COCHC2H5CO2C 2H5
CH 3COCHCH3COCH 3
CH 3COCH 2COC 6H5
C 6H5COCH 2COCF 3
CH 3COCH 2CHO
CH 3 COCH2 CO2CH 3
CH 3SO2CH 2SO2CH 3
CH 3SO2CH(COCH3)2
C 2H5NO2
C 2H5O2CCH 2 NO2
CH 2(NO2)2
CH 3COCH 2Cl
CH 3COCH 2CO2C 2H5
CH 3COCH 2COCH 3
CH 3COCHBrCOCH3
CH 3COCH 2COCF 3
C 6H5COCH 2NC 5H5
CH(COCH3)3
CH 3SO2CH 3
CH(SO2CH 3)3
CH 2(CN) 2
C 2H5O2CCH 2CN
CH 3CO2C 2H5
CHC 2H5(CO2C 2H5)2
CH 3CONH2
O
S

10.29
7
5.1
strong
15
12.7
11
9.4
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
74
74
74
74
74
74
74
74

6.10

74

O
CF3

CO2Et

10.96

74

7.82
4
9.21
strong
13.3
~ 24

74
2
2
74
74
74

10.5

74

CH 2(CHO)2

10.1
5

74
74

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)

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

O
CH3
O

Dinitromethane
Potassium cyanide
CH(CN)3
CH 2(CO2C 2H5)2
CH 3CO2H
OEt
O

CH3
O

28
28
28
28
28

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