pKa Table.1

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Transkript

pKa Table.1
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
O
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
+
H
OH
OH
11.3 (20.1)
-1.8
S
Me
Me
Ph
OH
N
O H
OH
N
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
H
(17.1)
PEROXIDES
R= H
trans-CO2H
-6.2
H
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
S
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
3
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
N
(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
O
N-Me morpholine
R
7.38
NO2
+
O2N
NH3
-9.3
NO2
O
Et
N+ H
DABCO
O
2.97, 8.82
(2.97, 8.93)
N+
N
H
6.90, 9.95
+NH
3
+NH
3
Proton Sponge
PhCN+H
+NH
3
-9.0, 12.0
(--, 7.50)
(21.6)
O
O
Ac2NH
8.30
O
NH
( )n
O
(20.8)
O
NH
Ph
(17.9)
R
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
O
+
N
N
(19.8)
N
(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
N
H
H
+
NH
(18.6)
X
S
DMAP
Me2N
N
HN
N
+
(23.0)
NH
X= O (14.8)
X= S (11.8)
(17.2)
PROTONATED HETEROCYCLES
(16.4)
N
(11.9)
X= O (24)
X X= S (13.3)
N
H
X
PhSO2NHNH2
PhNHNHPh
H
N
N
Me
(18.9)
(20.95)
N
(21.6)
NHNH2
R
O
(17.3)
(15.0)
R= Me
Ph
HETEROCYCLES
(17.5)
R = Me
Ph
(16.1)
CF3 6.3 (9.7)
MeSO2NHPh
(12.9)
RSO2NH2
O
n= 1 (24.1)
n= 2 (26.4)
(14.7)
8.88 (13.7)
(NH)
OH
SULFONAMIDE
N
Bn
O
NH
O
NH
O
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)
O
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
O
Me
O
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)
O
13
S
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
N
O
(18.2)
(18.0)
Me2N
(17.2)
Me
S
~36
(25.7)
Me2N
X=
19-20 (27.1)
O
(28.3)
n
Me
n=
i-Pr
O
Ph
O
X
(26.3)
[30.2 (THF)]
Ph
LiO
t-Bu O
Ph
O
15
Et
9
(26.5)
(19.8)
(18.7)
(13.3)
(12.5)
(27.7)
S
O
Et2N
20
X= H
Ph
SPh
COCH3
SO2Ph
O
Me2N
Me
X
(14.2)
OMe
(26.9)
Me
Me
O
11
MeO
(26.1)
Me
(20.0)
AMIDES
p-COPh
Me
N+Me3
Me
O
PhCH3
HCCH
(23.6)
EtO
43
Ph3CH
Ph
O
O
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
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)
O
O
O
(28.1)
(29.0)
(25.5)
O
(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)
N
N
(28.2)
Ph
(26.7)
Ph
(23.0)
N+
Ph
(25.2)
O-
O
S
(30.2)
Ph
(30.0)
Ph
(35.1)
(29.0)
(29.0)
O
Ph
S
X
X= H
Ph
SOPh
(33)
(27.2)
(18.2)
O
Ph
(24.5)
S
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
S
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
S
S
S
(22.3)
CHPh2
O
S
(27.6)
(30.7)
Me
(24.5)
CF3
O
(33)
CF3
O
Me
NMe
Me
N+Me2
(14.4)
Me
NTs
O
CH2Cl
CF3
Et
S
(31.1)
Me
O
(18.8)
Me
O
(21.8)
S
i-Pr
O
(26.6)
S
O
(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)
O
S
NTs
S
X
O
R
R= Me
i-Pr
O
O
S
Ph
NTs
X
X=
X
Me
S
N
S
X= H
Ph
SPh
S
(30.1)
O
S
(PhS)2CHPh
Ph
Me
Me
(30.5)
S
H
SULFONES
O
(30.8)
(20.8)
(18.7)
(16.9)
(11.8)
(30.8)
(20.5)
(11.0)
(24.9)
S
Substrate pKa H2O (DMSO)
SULFOXIDES
PhSCH2X
X= Ph
CN
COCH3
COPh
NO2
SPh
SO2Ph
SO2CF3
POPh2
HETERO-AROMATICS
pKa H2O (DMSO)
Substrate
SULFIDES
X
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)
O
(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
X
Ph
(27.6)
CN
CO2Et
(16.4)
Cl
SiMe3
n=
(18.6)
(26.2)
(28.8)
3
(26.9)
4
(17.8)
5
6
(16.0)
(17.9)
(15.8)
7
X
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
n
(EtO)2P
REFERENCES
DMSO:
CH2SPh
CH2SO2Ph
CH2COPh
O
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
O
N
H
N
H
N
H
O
O
N
N
N
H
N
H
N
N
O
O
N
H
N
H
15.0
12.1
O
N
H
26.4
O
24.0
Me
O
S
S
H
H
N
H
S
N
H
N
H
N
Me
S
Me
N+
Me
Me
N
N
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
2
Phenazine
24
Phosphates
3
Pyridine
25
Carboxylic acids
4, 8
Pyrazine
26
Aliphatic
4, 8
Aromatic
7, 8
Quinoline
27
Phenols
9
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
α-glycero1.40, 6.44
β-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) 10–OOC(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
α-keto-β-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
H
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
2
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
2
4.03, 5.31
2
4.37, 6.51
2
4.23, 5.53
2
4.34, 6.76
2
4.10, 5.46
2
4.44, 5.79
2
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
β-dihydrolysergol
6.33
6.08
6.8, -7.4, -8.2, --
2
2
2
2
2
Lysergic acid
α-dihydrolysergic
ergometrinine
α-dihydrolysergol
6-methylergoline
isolysergic acid
γ-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)3C–HO3P–O3SH2N(CH 3)2N–HO3As–O2CCH 3NH-
Substituted benzoic acids (ref. 2)
o
m
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*
p
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
β-carboxymethylaminopropionic
3.61, 9.46
α,α-diaminobutyric
1.85, 8.24, 10.44
Di-(carboxymethyl)-aminomethyl phosphonic
acid
2.00, 2.25, 5.57, 10.76
α,β-dimercaptosuccinic
2.40, 3.46, 9.44, 11.82
Ethylenediamine-N,N-diacetic
5.58, 11.05
α-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
α-Bromobutyric acid
2.97
N-(carbamoylmethyl)-imino-diacetic acid
2.30, 6.60
Cyanomethyliminodiacetic
3.06, 4.34
α,β-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
β-hydroxybutyric
4.39
β-hydroxypropionic
3.73
Iminodiacetic*
2.98, 9.89
β-iodopropionic*
4.04
N-isopropylaminoacetic
2.36, 10.06
α-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
p
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=R•CH2 •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 CH•OH
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
α-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
α-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
α-Aminobutyric acid 2.55
9.60
α-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
β-Alanine
3.60
10.19
6
γ-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
β-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
Gly•Ala (L) or (D)
3.17
8.23
Ala•Gly (L) or (D)
3.16
8.24
Gly•Ala•Ala (LL)
3.38
8.10
Gly•Ala•Ala (LD)
3.30
8.17
Ala•Ala•OH (DD)
3.30
8.14
Ala•Ala•OH (LD)
3.12
8.30
H•Ala•Ala•Ala•OH (3L)
3.39
8.03
H•Ala•Ala•Ala•OH (LLD)
3.37
8.05
H•Ala-Ala-Ala•OH (LDL)
3.31
8.13
H•Ala-Ala-Ala•OH (DLL)
3.37
8.06
H-Ala-Ala-Ala•OH (3D)
3.39
8.06
H•Ala-Ala-Ala-Ala•OH (4L)
3.42
7.94
H•Ala-Ala-Ala-Ala•OH (LLDL)
3.24
7.93
H•Ala-Ala-Ala-Ala•OH (LDLL)
3.22
7.99
H•Ala-Ala-Ala-Ala•OH (DLLL)
3.42
7.99
H•Lys-Ala•OH (LL)
3.22
7.62
10.70
H•Lys-Ala•OH (LD)
3.00
7.74
10.63
H•Ala-Lys-Ala•OH (3L)
3.15
7.65
10.30
H•Ala-Lys-Ala•OH (LDL)
3.33
7.97
10.36
H•Ala-Lys-Ala•OH (LLD)
3.29
7.84
10.49
H•Ala-Lys-Ala-Ala•OH (4L)
3.58
8.01
10.58
H•Ala-Lys-Ala•OH (LDLL)
3.32
8.01
10.37
H•Ala-Lys-Ala-Ala-Ala•OH (5L)
3.53
7.75
10.35
H•Ala-Lys-Ala-Ala-Ala•OH (LDLLL) 3.30
7.85
10.29
H•Lys-Lys•OH (LL)
3.01
7.53
10.05
H•Lys-Lys•OH (LD)
2.85
7.53
9.92
H•Lys-Lys•OH (3L)
3.08
7.34
9.80
H•Lys-Lys-Lys•OH (LDL)
2.91
7.29
9.79
H•Lys-Lys-Lys•OH (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
β-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
β-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-Butylcyclohexylα-Cyclohexylpyrroline
α-(p-Tolyl)pyrroline
α-Ethylpyrrolidine
α-Benzylpyrrolidine
N-methylhydroxylamine
Diethyl-
92
n-Propyl10.53
Trimethylsilymethyl10.96
CH 3ONH2
4.60
Allyl9.49
γ-Amino-n-butyric acid ester 9.71
sec-Butyl10.56
Cyclohexyl10.64
β-difluoroethyl7.52
Ethyl
10.63
Glycine ester
7.75
Hydroxyl5.97
Methoxy4.60
neo-Pentyl10.21
δ-Phenylbutyl
10.40
γ-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*
2
9.13
9.50*
9.83*
9.98*
9.71
10.15*
10.37
2
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
2
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
α-Ethylpyrroline
7.43
α-Benzylpyrroline7.08
2-Methylpiperidine
10.99
α-Cyclohexylpyrrolidine
10.80
α-(p-Tolyl)pyrrolidine
10.01
N,O-dimethylhydroxylamine 4.75
Acetanilide
+0.61
*thermodynamic value
2
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-β-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
β-Isopropylaminopropionitrile 8.0
β-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
β-Aminopropionitrile
7.7
9
β-Dimethylaminopropionitrile 7.0
9
β,β"-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
β,β,β"-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)3C–O3SH3N+
O2NHO2CC 2H5O2CF3CHOCl(CH 3)3SiC 2H5OCH 3–HO3As
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-α-amino-β-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
β-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-β-Mercaptoethyl-morpholine
1-Diethylamino-butan- (4)
7.95, 10.7
8.00, 10.8
6.65, 9.8
10.1
Methyl-[β-diethylamino-ethyl]sulfide 9.8
N-Diethyl-cysteamine
7.8, 10.75
N-β-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
4
6
7
N
8
5
N
2
N
N
Isoquinoline 5.14*
Pyridine 5.14*
pK (20°)
6
3
Benzoquinoline 5.05*
Quinoline 4.85*
4
7
3
8
2
N
9
N
N
N
1
10
N
Phenanthridine 3.30a
7,8-Benzoquinoline
4.25*
5,6-Benzoquinoline
5.15*
Acridine 5.60
N
N
2,3-Benzacridine 4.52a
3,4-Benzacridine 4.70*
1,2-Benzacridine 3.45a
N
N
N
N
N
N
Pyrazine 0.37*
Pyrimidine 1.10*
Pyridazine 2.10*
N
N
N
N
N
Quinazoline 3.31*
Phthalazine 3.39*
Cinnoline 2.64*
a
N
N
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
a
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
α,α'-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
6
7
8
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
OxBenzα-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
ψ-Ephedrine
9.22
N-Methyl-ψ-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-β-Mercaptoethyl-morpholine 6.65, 9.8
1-Diethylamino-butan- (4) 10.1
5
Methyl-[β-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-Β-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
Β-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
O
Dinitromethane
Potassium cyanide
CH(CN)3
CH 2(CO2C 2H5)2
CH 3CO2H
OEt
O
O
CH3
O
O
28
28
28
28
28
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