Dissociation Constants of Organic Acids and Bases

This table lists the dissociation (ionization) constants of over

1070 organic acids, bases, and amphoteric compounds. All data
apply to dilute aqueous solutions and are presented as values of
pKa, which is defined as the negative of the logarithm of the equilibrium constant Ka for the reaction

BH+ + OH- . This is related to Ka by

pKa + pKb = pKwater = 14.00 (at 25 C)

Compounds are listed by molecular formula in Hill order.

References

HA H+ + A-

i.e.,

Ka = [H+][A-]/[HA]

where [H+], etc. represent the concentrations of the respective

species in mol/L. It follows that pKa = pH + log[HA] log[A-], so
that a solution with 50% dissociation has pH equal to the pKa of
the acid.
Data for bases are presented as pKa values for the conjugate acid,
i.e., for the reaction
BH+ H+ + B

In older literature, an ionization constant Kb was used for the reaction B + H2O
Mol. form.
CHNO
CH2N2
CH2O
CH2O2
CH3NO2
CH3NS2
CH4N2O
CH4N2S
CH4O
CH4S
CH5N
CH5NO
CH5N3
C2HCl3O
C2HCl3O2
C2HF3O2
C2H2Cl2O2
C2H2O3
C2H2O4

Name
Cyanic acid
Cyanamide
Formaldehyde
Formic acid
Nitromethane
Carbamodithioic acid
Urea
Thiourea
Methanol
Methanethiol
Methylamine
O-Methylhydroxylamine
Guanidine
Trichloroacetaldehyde
Trichloroacetic acid
Trifluoroacetic acid
Dichloroacetic acid
Glyoxylic acid
Oxalic acid

C2H3BrO2
C2H3ClO2
C2H3Cl3O
C2H3FO2
C2H3F3O
C2H3IO2
C2H3NO4
C2H3N3
C2H3N3
C2H4N2
C2H4O
C2H4OS
C2H4O2
C2H4O2S
C2H4O3
C2H5N

Bromoacetic acid
Chloroacetic acid
2,2,2-Trichloroethanol
Fluoroacetic acid
2,2,2-Trifluoroethanol
Iodoacetic acid
Nitroacetic acid
1H-1,2,3-Triazole
1H-1,2,4-Triazole
Aminoacetonitrile
Acetaldehyde
Thioacetic acid
Acetic acid
Thioglycolic acid
Glycolic acid
Ethyleneimine

8-42

Step

1
2

t/C
25
29
25
25
25
25
25
25
25
25
25
25
25
20
25
25
25
25
25
25
25
25
25
25
25
24
20
20
25
25
25
25
25
25
25

pKa
3.7
1.1
13.27
3.75
10.21
2.95
0.10
-1
15.5
10.33
10.66
12.5
13.6
10.04
0.66
0.52
1.35
3.18
1.25
3.81
2.90
2.87
12.24
2.59
12.37
3.18
1.48
1.17
2.27
5.34
13.57
3.33
4.756
3.68
3.83
8.04

1. Perrin, D. D., Dissociation Constants of Organic Bases in Aqueous

Solution, Butterworths, London, 1965; Supplement, 1972.
2. Serjeant, E. P., and Dempsey, B., Ionization Constants of Organic Acids
in Aqueous Solution, Pergamon, Oxford, 1979.
3. Albert, A., Ionization Constants of Heterocyclic Substances, in
Katritzky, A. R., Ed., Physical Methods in Heterocyclic Chemistry,
Academic Press, New York, 1963.
4. Sober, H.A., Ed., CRC Handbook of Biochemistry, CRC Press, Boca
Raton, FL, 1968.
5. Perrin, D. D., Dempsey, B., and Serjeant, E. P., pKa Prediction for
Organic Acids and Bases, Chapman and Hall, London, 1981.
6. Albert, A., and Serjeant, E. P., The Determination of Ionization
Constants, Third Edition, Chapman and Hall, London, 1984.
7. ONeil, M.J., Ed., The Merck Index, 14th Edition, Merck & Co.,
Whitehouse Station, NJ, 2006.
Mol. form.
C2H5NO
C2H5NO2
C2H5NO2
C2H5NO2

Name
Acetamide
Acetohydroxamic acid
Nitroethane
Glycine

C2H6N2
C2H6O
C2H6OS
C2H6O2
C2H7AsO2

Ethanimidamide
Ethanol
2-Mercaptoethanol
Ethyleneglycol
Dimethylarsinic acid

C2H7N
C2H7N
C2H7NO
C2H7NO3S

Ethylamine
Dimethylamine
Ethanolamine

C2H7NS

2-Aminoethanesulfonic
acid
Cysteamine

C2H7N5

Biguanide

C2H8N2

1,2-Ethanediamine

C2H8O7P2

1-Hydroxy-1,1 diphosphonoethane

C3H2O2
C3H3NO
C3H3NO
C3H3NO2
C3H3NS
C3H3N3O3

2-Propynoic acid
Oxazole
Isoxazole
Cyanoacetic acid
Thiazole
Cyanuric acid

C3H4N2
C3H4N2

1H-Pyrazole
Imidazole

Step

1
2

1
2

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

1
2
3

t/C
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25

25
25

25
33
25
25
25

25
25

pKa
15.1
8.70
8.46
2.35
9.78
12.1
15.5
9.72
15.1
1.57
6.27
10.65
10.73
9.50
1.5
9.06
8.27
10.53
11.52
2.93
9.92
6.86
1.35
2.87
7.03
11.3
1.84
0.8
-2.0
2.47
2.52
6.88
11.40
13.5
2.49
6.99

Dissociation Constants of Organic Acids and Bases

Mol. form.
C3H4N2S
C3H4O
C3H4O2
C3H4O3
C3H4O4

Name
2-Thiazolamine
Propargyl alcohol
Acrylic acid
Pyruvic acid
Malonic acid

C3H4O5

Hydroxypropanedioic
acid
3-Bromopropanoic acid
2-Chloropropanoic acid
3-Chloropropanoic acid
3-Aminopropanenitrile

C3H5BrO2
C3H5ClO2
C3H5ClO2
C3H6N2
C3H6N6
C3H6O
C3H6O2
C3H6O2S
C3H6O3
C3H6O3
C3H6O4
C3H7N
C3H7N
C3H7NO
C3H7NO2

1,3,5-Triazine-2,4,6 triamine
Allyl alcohol
Propanoic acid
(Methylthio)acetic acid
Lactic acid
3-Hydroxypropanoic acid
Glyceric acid
Allylamine
Azetidine
2-Propanone oxime
L-Alanine

C3H7NO2

-Alanine

C3H7NO2

Sarcosine

C3H7NO2S

L-Cysteine

C3H7NO3

L-Serine

C3H7NO5S

DL-Cysteic acid

C3H7N3O2
C3H8O2

Glycocyamine

C3H8O3
C3H9N
C3H9N
C3H9N
C3H9NO
C3H9NO
C3H10N2

Ethylene glycol
monomethyl ether
Glycerol
Propylamine
Isopropylamine
Trimethylamine
2-Methoxyethylamine
Trimethylamine oxide
1,2-Propanediamine, ()

C3H10N2

1,3-Propanediamine

C3H10N2O

1,3-Diamino-2-propanol

C3H11N3

1,2,3-Triaminopropane

C4H4FN3O
C4H4N2
C4H4N2
C4H4N2
C4H4N2O2
C4H4N2O3
C4H4N2O5

Flucytosine
Pyrazine
Pyrimidine
Pyridazine
Uracil
Barbituric acid
Alloxanic acid

Step

1
2
1
2

1
2
1
2
1
2
1
2
3
1
2
1
2
3

1
2
1
2
1
2
1
2

t/C
20
25
25
25
25
25

25
25
25
20
25

pKa
5.36
13.6
4.25
2.39
2.85
5.70
2.42
4.54
4.00
2.83
3.98
7.80
5.00

25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25

15.5
4.87
3.66
3.86
4.51
3.52
9.49
11.29
12.42
2.34
9.87
3.55
10.24
2.21
10.1
1.5
8.7
10.2
2.19
9.21
1.3
1.9
8.70
2.82
14.8

25
25
25
25
25
20
25
25
25
25
20
20
20
20

14.15
10.54
10.63
9.80
9.40
4.65
9.82
6.61
10.55
8.88
9.69
7.93
9.59
7.95
3.26
0.65
1.23
2.24
9.45
4.01
6.64

20
20
20
25
25
25

8-43
Mol. form.
C4H4N4O2
C4H4O2
C4H4O4

Name
5-Nitropyrimidinamine
2-Butynoic acid
Maleic acid

C4H4O4

Fumaric acid

C4H4O5

Oxaloacetic acid

C4H5N
C4H5NO2
C4H5N3
C4H5N3
C4H5N3O

Pyrrole
Succinimide
2-Pyrimidinamine
4-Pyrimidinamine
Cytosine

C4H5N3O2
C4H6N2
C4H6N4O3
C4H6N4O3S2
C4H6O2
C4H6O2
C4H6O2
C4H6O3
C4H6O3
C4H6O4

6-Methyl-1,2,4-triazine 3,5(2H,4H)-dione
1-Methylimidazol
Allantoin
Acetazolamide
trans-Crotonic acid
3-Butenoic acid
Cyclopropanecarboxylic acid
2-Oxobutanoic acid
Acetoacetic acid
Succinic acid

C4H6O4

Methylmalonic acid

C4H6O5

Malic acid

C4H6O6

DL-Tartaric acid

C4H6O6

meso-Tartaric acid

C4H6O6

L-Tartaric acid

C4H6O8
C4H7ClO2
C4H7ClO2
C4H7ClO2
C4H7NO2
C4H7NO3
C4H7NO4

Dihydroxytartaric acid
2-Chlorobutanoic acid
3-Chlorobutanoic acid
4-Chlorobutanoic acid
4-Cyanobutanoic acid
N-Acetylglycine
Iminodiacetic acid

C4H7NO4

L-Aspartic acid

C4H7N3O

Creatinine

C4H7N5
C4H8N2O3

2,4,6-Pyrimidinetriamine
L-Asparagine

C4H8N2O3

N-Glycylglycine

C4H8O2
C4H8O2
C4H8O3
C4H8O3
C4H8O3
C4H9N

Butanoic acid
2-Methylpropanoic acid
3-Hydroxybutanoic acid, ()
4-Hydroxybutanoic acid
Ethoxyacetic acid
Pyrrolidine

Step

1
2
1
2
1
2
3

1
2

1
2
1
2
1
2
1
2
1
2
1
2

1
2
1
2
3
1
2
1
2
1
2

t/C
20
25
25
25
25
25
25
25
25
25
25
20
20

pKa
0.35
2.62
1.92
6.23
3.02
4.38
2.55
4.37
13.03
-3.8
9.62
3.45
5.71
4.60
12.16
7.6

25
25

6.95
8.96
7.2
4.69
4.34
4.83
2.50
3.6
4.21
5.64
3.07
5.76
3.40
5.11
3.03
4.37
3.17
4.91
2.98
4.34
1.92
2.86
4.05
4.52
2.42
3.67
2.98
9.89
1.99
3.90
9.90
4.8
9.2
6.84
2.1
8.80
3.14
8.17
4.83
4.84
4.70
4.72
3.65
11.31

25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25

25
25

25
25
25
25
20
20
20
25
25
20
25
25
18
25

Dissociation Constants of Organic Acids and Bases

8-44
Mol. form.
C4H9NO
C4H9NO2

Name
Morpholine
2-Methylalanine

C4H9NO2
C4H9NO2

N,N-Dimethylglycine
DL-2-Aminobutanoic acid

C4H9NO2

4-Aminobutanoic acid

C4H9NO2S

DL-Homocysteine

C4H9NO3

L-Threonine

C4H9NO3

L-Homoserine

C4H9N3O2

Creatine

C4H10N2

Piperazine

C4H10N2O2

2,4-Diaminobutanoic acid

C4H10O4
C4H11N
C4H11N
C4H11N
C4H11N
C4H11NO3

1,2,3,4-Butanetetrol
Butylamine
sec-Butylamine
tert-Butylamine
Diethylamine

C4H12N2

Tris(hydroxymethyl)
methylamine
1,4-Butanediamine

C5H4BrN
C5H4ClN
C5H4ClN
C5H4ClN
C5H4FN
C5H4N2O2
C5H4N4

3-Bromopyridine
2-Chloropyridine
3-Chloropyridine
4-Chloropyridine
2-Fluoropyridine
4-Nitropyridine
1H-Purine

C5H4N4O
C5H4N4O
C5H4N4O3
C5H4N4S

Hypoxanthine
Allopurinol
Uric acid

C5H4O2S
C5H4O2S
C5H4O3
C5H4O3
C5H5N
C5H5NO

1,7-Dihydro-6H purine-6-thione
2-Thiophenecarboxylic acid
3-Thiophenecarboxylic acid
2-Furancarboxylic acid
3-Furancarboxylic acid
Pyridine
2-Pyridinol

C5H5NO

3-Pyridinol

C5H5NO

4-Pyridinol

C5H5NO

2(1H)-Pyridinone

C5H5NO
C5H5NO2

Pyridine-1-oxide
1H-Pyrrole-2-carboxylic
acid

Step
1
2
1
2
1
2
1
2
3
1
2
1
2
1
2
1
2
1
2
3

t/C
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
20

1
2

1
2

1
2

1
2
1
2
1
2
1
2

25
25
25
25
25
25
25
25
20
20
25
12

25
25
25
25
25
20
20
20
20
20
20
20
20
24
20

pKa
8.50
2.36
10.21
9.89
2.29
9.83
4.031
10.556
2.22
8.87
10.86
2.09
9.10
2.71
9.62
2.63
14.3
9.73
5.33
1.85
8.24
10.44
13.9
10.60
10.56
10.68
10.84
8.3
10.80
9.63
2.84
0.49
2.81
3.83
-0.44
1.61
2.30
8.96
8.7
10.2
3.89
7.77
11.17
3.49
4.1
3.16
3.9
5.23
0.75
11.65
4.79
8.75
3.20
11.12
0.75
11.65
0.79
4.45

Mol. form.
C5H5NO2
C5H5N3O
C5H5N5

Name

1H-Pyrrole-3-carboxylic
acid
Pyrazinecarboxamide
Adenine

C5H5N5O
C5H6N2
C5H6N2
C5H6N2
C5H6N2
C5H6N2O2
C5H6O4

Guanine
2-Pyridinamine
3-Pyridinamine
4-Pyridinamine
2-Methylpyrazine
Thymine

C5H6O4

trans-1-Propene-1,2 dicarboxylic acid

C5H6O4
C5H6O5
C5H7NO3

1,1-Cyclopropanedi carboxylic acid

1-Propene-2,3 dicarboxylic acid

2-Oxoglutaric acid

C5H7NO3
C5H7N3
C5H7N3
C5H7N3O4
C5H8N2
C5H8N4O3S2
C5H8O2
C5H8O4
C5H8O4

5,5-Dimethyl-2,4 oxazolidinedione
L-Pyroglutamic acid
2,5-Pyridinediamine
Methylaminopyrazine
Azaserine
2,4-Dimethylimidazole
Methazolamide
trans-3-Pentenoic acid
Dimethylmalonic acid
Glutaric acid

C5H8O4

Methylsuccinic acid

C5H9NO2

L-Proline

C5H9NO3
C5H9NO3

5-Amino-4-oxopentanoic
acid
trans-4-Hydroxyproline

C5H9NO4

L-Glutamic acid

C5H9N3

Histamine

C5H10N2O3
C5H10N2O3

Glycylalanine
L-Glutamine

C5H10N2O4

Glycylserine

C5H10O2
C5H10O2
C5H10O2
C5H10O2
C5H10O4
C5H10O5
C5H10O5
C5H11N
C5H11N
C5H11NO
C5H11NO2

Pentanoic acid
2-Methylbutanoic acid
3-Methylbutanoic acid
2,2-Dimethylpropanoic acid
D-2-Deoxyribose
L-Ribose
D-Xylose
Piperidine
N-Methylpyrrolidine
4-Methylmorpholine
L-Valine

Step

1
2

1
2
1
2
1
2
1
2

t/C
20

pKa
5.00

40
20
25
25
27
25
25
25
25
25
25
25
25
25
37

0.5
4.3
9.83
9.92
6.82
6.04
9.11
1.45
9.94
1.82
7.43
3.09
4.75
3.85
5.45
2.47
4.68
6.13

25
20
25
25

1
2
1
2
1
2
1
2
1
2
1
2
3
1
2
1
2
1
2

1
2

25
25
18
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
20
25
25
20
25
25
18
25
25
25
25
25

3.32
6.48
3.39
8.55
8.36
7.30
4.51
3.15
4.32
5.42
4.13
5.64
1.95
10.64
4.05
8.90
1.82
9.66
2.13
4.31
9.67
6.04
9.75
3.15
2.17
9.13
2.98
8.38
4.83
4.80
4.77
5.03
12.61
12.22
12.14
11.123
10.46
7.38
2.29
9.74

Dissociation Constants of Organic Acids and Bases

Mol. form.
C5H11NO2

Name
DL-Norvaline

C5H11NO2

L-Norvaline

C5H11NO2

N-Propylglycine

C5H11NO2

5-Aminopentanoic acid

C5H11NO2
C5H11NO2S

Betaine
L-Methionine

C5H12N2O
C5H12N2O2

Tetramethylurea
L-Ornithine

C5H13N
C5H13N
C5H13N
C5H13N
C5H13N
C5H13N
C5H14NO
C5H14N2

Pentylamine
3-Pentanamine
3-Methyl-1-butanamine
2-Methyl-2-butanamine
2,2-Dimethylpropylamine
Diethylmethylamine
Choline
1,5-Pentanediamine

C6H3Cl3N2O2
C6H3N3O7
C6H4Cl2O
C6H4N2O5
C6H4N2O5
C6H4N4
C6H5BrO
C6H5BrO
C6H5BrO
C6H5Br2N
C6H5ClO
C6H5ClO
C6H5ClO
C6H5Cl2N
C6H5FO
C6H5FO
C6H5FO
C6H5IO
C6H5IO
C6H5IO
C6H5NO
C6H5NO
C6H5NO2
C6H5NO2

4-Amino-3,5,6-trichloro 2-pyridinecarboxlic acid

2,4,6-Trinitrophenol
2,3-Dichlorophenol
2,4-Dinitrophenol
2,5-Dinitrophenol
Pteridine
2-Bromophenol
3-Bromophenol
4-Bromophenol
3,5-Dibromoaniline
2-Chlorophenol
3-Chlorophenol
4-Chlorophenol
2,4-Dichloroaniline
2-Fluorophenol
3-Fluorophenol
4-Fluorophenol
2-Iodophenol
3-Iodophenol
4-Iodophenol
2-Pyridinecarboxaldehyde
4-Pyridinecarboxaldehyde
Nitrobenzene
2-Pyridinecarboxylic acid

C6H5NO2

3-Pyridinecarboxylic acid

C6H5NO2

4-Pyridinecarboxylic acid

C6H5NO3
C6H5NO3
C6H5NO3
C6H5N3
C6H5N5O

2-Nitrophenol
3-Nitrophenol
4-Nitrophenol
1H-Benzotriazole

C6H5N5O2

2-Amino-4 hydroxypteridine
Xanthopterin

Step
1
2
1
2
1
2
1
2
1
2
1
2
3

1
2

1
2
1
2
1
2

1
2
2

t/C

25
25
25
25
25
25
0
25
25
25
25
25
25
17
25
19
25
25
25
25
25

24
25
25
15
20
25
25
25
25
25
25
25
22
25
25
25
25
25
25
25
30
0
20
20
25
25
25
25
25
25
25
20
20
20
20

pKa
2.36
9.72
2.32
9.81
2.35
10.19
4.27
10.77
1.83
2.13
9.27
2
1.71
8.69
10.76
10.63
10.59
10.60
10.85
10.15
10.35
13.9
10.05
10.93
3.6
0.42
7.44
4.07
5.15
4.05
8.45
9.03
9.37
2.34
8.56
9.12
9.41
2.05
8.73
9.29
9.89
8.51
9.03
9.33
12.68
12.05
3.98
0.99
5.39
2.00
4.82
1.77
4.84
7.23
8.36
7.15
1.6
2.27
7.96
6.59

8-45
Mol. form.
C6H6BrN
C6H6BrN
C6H6BrN
C6H6ClN
C6H6ClN
C6H6ClN
C6H6FN
C6H6FN
C6H6FN
C6H6IN
C6H6IN
C6H6IN
C6H6N2O
C6H6N2O

Name
2-Bromoaniline
3-Bromoaniline
4-Bromoaniline
2-Chloroaniline
3-Chloroaniline
4-Chloroaniline
2-Fluoroaniline
3-Fluoroaniline
4-Fluoroaniline
2-Iodoaniline
3-Iodoaniline
4-Iodoaniline
3-Pyridinecarboxamide

C6H6N2O2
C6H6N2O2
C6H6N2O2
C6H6O
C6H6O2

2-Pyridinecarbox aldehyde oxime

2-Nitroaniline
3-Nitroaniline
4-Nitroaniline
Phenol
p-Hydroquinone

C6H6O2

Pyrocatechol

C6H6O2

Resorcinol

C6H6O2S
C6H6O3S
C6H6O4

Benzenesulfinic acid
Benzenesulfonic acid

C6H6O4S
C6H6O4S
C6H6O6
C6H6O6

1
2
1
2
1
2

3-Hydroxybenzene sulfonic acid

4-Hydroxybenzene sulfonic acid
cis-1-Propene-1,2,3 tricarboxylic acid

C6H6S
C6H7BO2
C6H7N
C6H7N
C6H7N
C6H7N
C6H7NO
C6H7NO

3-Aminophenol

C6H7NO

4-Aminophenol

C6H7NO
C6H7NO
C6H7NO
C6H7NO3S

2-Methoxypyridine
3-Methoxypyridine
4-Methoxypyridine

C6H7NO3S

3-Aminobenzenesulfonic
acid

C6H8N2
C6H8N2

1
2

5-Hydroxy-2-(hydroxy methyl)-4H-pyran-4-one

trans-1-Propene-1,2,3 tricarboxylic acid

Benzenethiol
Benzeneboronic acid
Aniline
2-Methylpyridine
3-Methylpyridine
4-Methylpyridine
2-Aminophenol

C6H7NO3S

Step
3

1
2

1
2
1
2
1
2

2-Aminobenzenesulfonic
acid

4-Aminobenzenesulfonic
acid
N-Methylpyridinamine
o-Phenylenediamine

t/C
20
25
25
25
25
25
25
25
25
25
25
25
25
20
20
20
25
25
25
25
25
25
25
25
25
25
20
25

pKa
9.31
2.53
3.53
3.89
2.66
3.52
3.98
3.20
3.59
4.65
2.54
3.58
3.81
3.3
3.59
10.18
-0.25
2.46
1.02
9.99
9.85
11.4
9.34
12.6
9.32
11.1
1.3
0.70
7.9

25

9.07

25

9.11

25

1.95

25
25
25
25
25
25
25
20
20
20
20
25
25
20
25
25
25

2.80
4.46
6.62
8.83
4.87
6.00
5.70
5.99
4.78
9.97
4.37
9.82
5.48
10.30
3.28
4.78
6.58
2.46

25

3.74

25

3.23

20
20

9.65
4.57

Dissociation Constants of Organic Acids and Bases

8-46
Mol. form.

Name

C6H8N2

m-Phenylenediamine

C6H8N2

p-Phenylenediamine

C6H8N2
C6H8O2
C6H8O2
C6H8O4

Phenylhydrazine
2,4-Hexadienoic acid
1,3-Cyclohexanedione

C6H8O6

2,2-Dimethyl-1,3 dioxane-4,6-dione
L-Ascorbic acid

C6H8O7

Citric acid

C6H8O7

Isocitric acid

C6H9NO6

Nitrilotriacetic acid

C6H9NO6

L--Carboxyglutamic acid

C6H9N3

4,6-Dimethylpyrimi dinamine
L-Histidine

C6H9N3O2
C6H10O2
C6H10O3
C6H10O4
C6H10O4
C6H11NO2

Cyclopentanecarboxylic
acid
Ethyl acetoacetate
3-Methylglutaric acid
Adipic acid

C6H11NO3
C6H11NO4

2-Piperidinecarboxylic
acid
Adipamic acid
2-Aminoadipic acid

C6H11N3O4

N-(N-Glycylglycyl)glycine

C6H11N3O4

Glycylasparagine

C6H12N2

Triethylenediamine

C6H12N2O4S2

L-Cystine

C6H12O2
C6H12O2
C6H12O6
C6H12O6
C6H12O6
C6H13N
C6H13N
C6H13N
C6H13NO

Hexanoic acid
4-Methylpentanoic acid
-D-Fructose
-D-Glucose
D-Mannose
Cyclohexylamine
1-Methylpiperidine
1,2-Dimethylpyrrolidine
N-Ethylmorpholine

Step
2
1
2
1
2

t/C
20
20
20
20
20
15
25
25

pKa
0.80
5.11
2.50
6.31
2.97
8.79
4.76
5.26
5.1

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

25
16
25
25
25
25
25
25
20
20
20
25
25
25
25
20

4.04
11.7
3.13
4.76
6.40
3.29
4.71
6.40
3.03
3.07
10.70
1.7
3.2
4.75
9.9
4.82

1
2
3

25
25
25
25

1.80
6.04
9.33
4.99

25
25
18
18
25
25
25
25
25
25
25
25
25
18

10.68
4.24
4.41
5.41
2.28
10.72
4.63
2.14
4.21
9.77
3.225
8.09
2.942
8.44
3.0
8.7
1
2.1
8.02
8.71
4.85
4.84
12.27
12.46
12.08
10.64
10.38
10.20
7.67

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

25
18
25
25
25
25
25
26
25

Mol. form.
C6H13NO2

L-Leucine

C6H13NO2

L-Isoleucine

C6H13NO2

L-Norleucine

C6H13NO2

6-Aminohexanoic acid

C6H13NO4

N,N-Bis(2-hydroxy ethyl)glycine
Citrulline

C6H13N3O3
C6H14N2
C6H14N2
C6H14N2

Name

cis-1,2-Cyclohexane diamine
trans-1,2-Cyclohexane diamine

C6H14N2O2

cis-2,5-Dimethyl piperazine
L-Lysine

C6H14N4O2

L-Arginine

C6H14O6
C6H15N
C6H15N
C6H15N
C6H15NO3
C6H16N2

D-Mannitol
Hexylamine
Diisopropylamine
Triethylamine
Triethanolamine
1,6-Hexanediamine

C6H16N2

N,N,N,N-Tetramethyl 1,2-ethanediamine
Hexamethyldisilazane
Pentafluorobenzoic acid

C6H19NSi2
C7HF5O2
C7H3Br2NO
C7H3N3O8
C7H4Cl3NO3
C7H4N2O6
C7H5BrO2
C7H5BrO2
C7H5BrO2
C7H5ClO2
C7H5ClO2
C7H5ClO2
C7H5FO2
C7H5FO2
C7H5FO2
C7H5F3O
C7H5F3O
C7H5IO2
C7H5IO2
C7H5IO2
C7H5NO
C7H5NO
C7H5NO
C7H5NO3S
C7H5NO4
C7H5NO4
C7H5NO4

3,5-Dibromo-4 hydroxybenzonitrile
2,4,6-Trinitrobenzoic acid
Triclopyr
2,4-Dinitrobenzoic acid
2-Bromobenzoic acid
3-Bromobenzoic acid
4-Bromobenzoic acid
2-Chlorobenzoic acid
3-Chlorobenzoic acid
4-Chlorobenzoic acid
2-Fluorobenzoic acid
3-Fluorobenzoic acid
4-Fluorobenzoic acid
2-(Trifluoromethyl)phenol
3-(Trifluoromethyl)phenol
2-Iodobenzoic acid
3-Iodobenzoic acid
4-Iodobenzoic acid
2-Hydroxybenzonitrile
3-Hydroxybenzonitrile
4-Hydroxybenzonitrile
Saccharin
2-Nitrobenzoic acid
3-Nitrobenzoic acid
4-Nitrobenzoic acid

Step
1
2
1
2
1
2
1
2
2

t/C
25
25
25
25
25
25
25
25
20

pKa
2.33
9.74
2.32
9.76
2.34
9.83
4.37
10.80
8.35

1
2
1
2
1
2
1
2
1
2
3
1
2
3

25
25
20
20
20
20
25
25
25
25
25
25
25
25
18
25
25
25
25
0
0
25
25

2.43
9.69
9.93
6.13
9.94
6.47
9.66
5.20
2.16
9.06
10.54
1.82
8.99
12.5
13.5
10.56
11.05
10.75
7.76
11.86
10.76
10.40
8.26
7.55
1.75
4.06

1
2
1
2

25

25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
18
25
25
25

0.65
2.68
1.43
2.85
3.81
3.96
2.90
3.84
4.00
3.27
3.86
4.15
8.95
8.68
2.86
3.87
4.00
6.86
8.61
7.97
11.68
2.17
3.46
3.43

Dissociation Constants of Organic Acids and Bases

Mol. form.
C7H5NO4
C7H5NO4
C7H5NO4
C7H5NO4

Name

2,3-Pyridinedicarboxylic
acid
2,4-Pyridinedicarboxylic
acid
2,6-Pyridinedicarboxylic
acid
3,5-Pyridinedicarboxylic
acid
Chlorothiazide

C7H6ClN3O4S2
C7H6F3N
C7H6F3N
C7H6N2
C7H6N2
C7H6N2
C7H6N2
C7H6O
C7H6O2
C7H6O2
C7H6O2
C7H6O2
C7H6O3

3-(Trifluoromethyl)aniline
4-(Trifluoromethyl)aniline
1H-Benzimidazole
2-Aminobenzonitrile
3-Aminobenzonitrile
4-Aminobenzonitrile
Benzaldehyde
Benzoic acid
Salicylaldehyde
3-Hydroxybenzaldehyde
4-Hydroxybenzaldehyde
2-Hydroxybenzoic acid

C7H6O3

3-Hydroxybenzoic acid

C7H6O3

4-Hydroxybenzoic acid

C7H6O4

2,4-Dihydroxybenzoic acid

C7H6O4
C7H6O4

2,5-Dihydroxybenzoic acid
3,4-Dihydroxybenzoic acid

C7H6O4
C7H6O5

3,5-Dihydroxybenzoic acid

C7H6O5
C7H7NO
C7H7NO2

3,4,5-Trihydroxybenzoic
acid
Benzamide
Aniline-2-carboxylic acid

C7H7NO2

Aniline-3-carboxylic acid

C7H7NO2

Aniline-4-carboxylic acid

C7H7NO3
C7H8ClN3O4S2

4-Amino-2-hydroxy benzoic acid

Hydrochlorothiazide

C7H8N4O2
C7H8N4O2
C7H8O
C7H8O
C7H8O
C7H8OS
C7H8O2
C7H8O2
C7H8O2
C7H8S
C7H9N

Theobromine
Theophylline
o-Cresol
m-Cresol
p-Cresol
4-(Methylthio)phenol
2-Methoxyphenol
3-Methoxyphenol
4-Methoxyphenol
Benzenemethanethiol
Benzylamine

Step
1
2
1

t/C
25
25
25

pKa
2.43
4.78
2.15

1
2
1

25
25
25

2.16
4.76
2.80

25
25
25
25
25
25
25
25
25
25
25
20
20
25
19
25
25
25
25
25
25
25
25
25
25
25

6.85
9.45
3.49
2.45
5.53
0.77
2.75
1.74
14.90
4.204
8.37
8.98
7.61
2.98
13.6
4.08
9.92
4.57
9.46
3.11
8.55
14.0
2.97
4.48
8.83
12.6
4.04
1.68

25

4.41

25
25
25
25
25
25
25

13
2.17
4.85
3.07
4.79
2.50
4.87
3.25

1
2

1
2
1
2
1
2
1
2
3
1
1
2
3
1

2,4,6-Trihydroxybenzoic
acid

1
2
1
2
1
2

1
2
1

18
25
25
25
25
25
25
25
25
25
25

7.9
9.2
7.89
8.77
10.29
10.09
10.26
9.53
9.98
9.65
10.21
9.43
9.34

8-47
Mol. form.
C7H9N
C7H9N
C7H9N
C7H9N
C7H9N
C7H9N
C7H9N
C7H9N
C7H9N
C7H9N
C7H9N
C7H9NO
C7H9NO
C7H9NO
C7H9NS
C7H9NS
C7H9N5

Name
2-Methylaniline
3-Methylaniline
4-Methylaniline
N-Methylaniline
2-Ethylpyridine
2,3-Dimethylpyridine
2,4-Dimethylpyridine
2,5-Dimethylpyridine
2,6-Dimethylpyridine
3,4-Dimethylpyridine
3,5-Dimethylpyridine
2-Methoxyaniline
3-Methoxyaniline
4-Methoxyaniline
2-(Methylthio)aniline
4-(Methylthio)aniline
2-Dimethylaminopurine

C7H11N3O2

L-1-Methylhistidine

C7H11N3O2

L-3-Methylhistidine

C7H12O2
C7H12O4

Cyclohexanecarboxylic acid
Heptanedioic acid

C7H12O4
C7H13NO4

Butylpropanedioic acid
-Ethylglutamic acid

C7H14O2
C7H14O6
C7H15N
C7H15N
C7H15NO3
C7H17N
C7H17N
C8H5NO2
C8H5NO2
C8H6N2
C8H6N2
C8H6N2
C8H6N2
C8H6N4O5
C8H6O3
C8H6O3
C8H6O4

Heptanoic acid
-Methylglucoside
1-Ethylpiperidine
1,2-Dimethylpiperidine,()
Carnitine
Heptylamine
2-Heptanamine
3-Cyanobenzoic acid
4-Cyanobenzoic acid
Cinnoline
Quinazoline
Quinoxaline
Phthalazine
Nitrofurantoin
3-Formylbenzoic acid
4-Formylbenzoic acid
Phthalic acid

C8H6O4

Isophthalic acid

C8H6O4

Terephthalic acid

C8H7ClO2
C8H7ClO2
C8H7ClO2
C8H7ClO3
C8H7ClO3
C8H7NO4
C8H7NO4
C8H7NO4
C8H8F3N3O4S2

2-Chlorobenzeneacetic acid
3-Chlorobenzeneacetic acid
4-Chlorobenzeneacetic acid
2-Chlorophenoxyacetic acid
3-Chlorophenoxyacetic acid
2-Nitrobenzeneacetic acid
3-Nitrobenzeneacetic acid
4-Nitrobenzeneacetic acid
Hydroflumethiazide

Step

1
2
1
2
3
1
2
3
1
2
1
1
2

1
2
1
2
1
2

t/C
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
20
20
25
25
25
25
25
25
25
25
25
5
25
25
25
25
23
25
25
25
19
25
25
20
29
20
20
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25
25

pKa
4.45
4.71
5.08
4.85
5.89
6.57
6.99
6.40
6.65
6.46
6.15
4.53
4.20
5.36
3.45
4.35
4.00
10.24
1.69
6.48
8.85
1.92
6.56
8.73
4.91
4.71
5.58
2.96
3.846
7.838
4.89
13.71
10.45
10.22
3.80
10.67
10.7
3.60
3.55
2.37
3.43
0.56
3.47
7.2
3.84
3.77
2.943
5.432
3.70
4.60
3.54
4.34
4.07
4.14
4.19
3.05
3.10
4.00
3.97
3.85
8.9

Dissociation Constants of Organic Acids and Bases

8-48
Mol. form.
C8H8N2
C8H8O2
C8H8O2
C8H8O2
C8H8O2
C8H8O2
C8H8O2
C8H8O2
C8H8O3
C8H8O3
C8H8O3
C8H8O3
C8H8O3
C8H8O4
C8H9NO
C8H9NO2
C8H9NO2
C8H9NO2
C8H9NO2
C8H10BrN
C8H10ClN
C8H10ClN
C8H10N2O2

Name
2-Methyl-1H-benzimidazole
o-Toluic acid
m-Toluic acid
p-Toluic acid
Benzeneacetic acid
1-(2-Hydroxyphenyl)ethanone
1-(3-Hydroxyphenyl)ethanone
1-(4-Hydroxyphenyl)ethanone
2-Methoxybenzoic acid
3-Methoxybenzoic acid
4-Methoxybenzoic acid
Phenoxyacetic acid
Mandelic acid

25
25
25
25
25
25
25
25
25
25
25
25
25
25

pKa
9.7
6.19
3.91
4.25
4.37
4.31
10.06
9.19
8.05
4.08
4.10
4.50
3.17
3.37
4.40

25
25

0.5
5.34

C9H6BrN
C9H7ClO2

3-Bromoquinoline

25

5.10

C9H7ClO2

25

5.04

C9H7ClO2

trans-m-Chlorocinnamic
acid

25
25

1.83
4.39
4.23

C9H7N
C9H7N
C9H7NO

trans-p-Chlorocinnamic
acid
Quinoline
Isoquinoline
2-Quinolinol

20

3.83

C9H7NO

3-Quinolinol

20

4.39

C9H7NO

4-Quinolinol

25

2.62

C9H7NO

6-Quinolinol
8-Quinolinol

C9H7NO

7-Isoquinolinol

1
2
1
2

25
25
25
25

C9H7NO3
C9H7NO3
C9H7NO3
C9H7N7O2S
C9H8N2
C9H8N2
C9H8N2
C9H8N2
C9H8N2
C9H8O2
C9H8O2
C9H8O2

2-Cyanophenoxyacetic acid
3-Cyanophenoxyacetic acid
4-Cyanophenoxyacetic acid
Azathioprine
2-Quinolinamine
3-Quinolinamine
4-Quinolinamine
1-Isoquinolinamine
3-Isoquinolinamine
cis-Cinnamic acid
trans-Cinnamic acid

25
25

5.12
5.07
3.89
9.83
7.43
4.43
4.18
5.20
9.74
10.52
5.5
8.9
10.6
8.64
9.70
6.70
10.76
2.13
7.43
5.15

C9H7NO

1
2

25
25
25
25
25
28
25
28
25
25

25
15
15
25
25

6.84
5.4
4.52
3.80
3.80
3.18
3.25

2,5-Hydroxybenzeneacetic
acid
Acetanilide
2-(Methylamino)benzoic
acid
3-(Methylamino)benzoic
acid
4-(Methylamino)benzoic
acid
N-Phenylglycine
4-Bromo-N,N dimethylaniline

1
2

3-Chloro-N,N dimethylaniline
4-Chloro-N,N dimethylaniline

C8H11N
C8H11N
C8H11N
C8H11N
C8H11N
C8H11NO
C8H11NO
C8H11NO
C8H11NO

N,N-Dimethyl-3 nitroaniline
N-Ethylaniline
N,N-Dimethylaniline
2,6-Dimethylaniline
Benzeneethanamine
2,4,6-Trimethylpyridine
2-Ethoxyaniline
3-Ethoxyaniline
4-Ethoxyaniline
4-(2-Aminoethyl)phenol

C8H11NO
C8H11NO2

2-(2-Methoxyethyl)pyridine
Dopamine

C8H11NO3

Norepinephrine

C8H11N3O6
C8H11N5

6-Azauridine
Phenylbiguanide

C8H12N2O3
C8H12O2

Barbital

C8H13NO2
C8H14O2S2
C8H14O4
C8H15NO
C8H15NO
C8H16N2O3
C8H16N2O3

Step
2
1

5,5-Dimethyl-1,3 cyclohexanedione
Arecoline
Thioctic acid
Octanedioic acid
Tropine
Pseudotropine
N-Glycylleucine
N-Leucylglycine

1
2

t/C

Mol. form.

Name

C8H16N2O4S2

Homocystine

C8H16O2
C8H16O2
C8H17N
C8H17N
C8H17NO

Octanoic acid
2-Propylpentanoic acid
2-Propylpiperidine,(S)
2,2,4-Trimethylpiperidine

C8H19N
C8H19N
C8H19N
C8H20N2

C9H8O4
C9H9Br2NO3
C9H9ClO2
C9H9ClO2
C9H9ClO2
C9H9I2NO3

trans-6-Propyl-3 piperidinol,(3S)
Octylamine
N-Methyl-2-heptanamine
Dibutylamine
1,8-Octanediamine

Step
2
1
2
3
4

30

1
2

trans-o-Chlorocinnamic
acid

-Methylenebenezene acetic acid

2-(Acetyloxy)benzoic acid
3,5-Dibromo-L-tyrosine

1
2
1
2
1
2
1
2
1
2
1
2

1
2
3

3-(3-Chlorophenyl) propanoic acid

pKa
8.2
1.59
2.54
8.52
9.44
4.89
4.6
10.9
11.04
10.3

25
17
21
20
20
25
25

10.65
10.99
11.25
11.00
10.1
2.69
4.23

25

4.29

25

4.41

20
20
20
20
20
20
20
20
20
20
25
25
20
20
25
25
25

4.90
5.40
-0.31
11.76
4.28
8.08
2.23
11.28
5.15
8.90
4.91
9.81
5.68
8.90
2.98
3.03
2.93
8.2
7.34
4.91
9.17
7.62
5.05
3.88
4.44
4.35

20
20
20
20
20
25
25

3-(2-Chlorophenyl) propanoic acid

3-(4-Chlorophenyl) propanoic acid

L-3,5-Diiodotyrosine

t/C
25
25
25
25
25
25

25

25

3.48
2.17
6.45
7.60
4.58

25

4.59

25

4.61

25

2.12

Dissociation Constants of Organic Acids and Bases

Mol. form.

Name

C9H9NO3
C9H9NO4

N-Benzoylglycine

C9H9NO4

3-(4-Nitrophenyl) propanoic acid

Carbendazim
Sulfathiazole
L-3-Iodotyrosine

C9H9N3O2
C9H9N3O2S2
C9H10INO3
C9H10N2
C9H10O2
C9H10O2
C9H10O2
C9H10O3

3-(2-Nitrophenyl) propanoic acid

2-Ethylbenzimidazole
3,5-Dimethylbenzoic acid
Benzenepropanoic acid
-Methylbenzeneacetic acid
-Hydroxy--methyl benezeneacetic acid
Methylclothiazide
N-Allylaniline
1-Indanamine

C9H11Cl2N3O4S2
C9H11N
C9H11N
C9H11NO2
4-(Dimethylamino) benzoic acid
Ethyl 4-aminobenzoate
C9H11NO2
L-Phenylalanine
C9H11NO2
C9H11NO3

L-Tyrosine

C9H11NO4

Levodopa

C9H12N2O2
C9H13N
C9H13NO3

Tyrosineamide
N-Isopropylaniline
Epinephrine

C9H13N2O9P

5-Uridylic acid

C9H13N3O5

Cytidine

C9H14ClNO
C9H14N2O3
C9H14N3O8P

Phenylpropanolamine
hydrochloride
Metharbital
3-Cytidylic acid

C9H14N4O3

Carnosine

C9H15NO3S

Captopril

C9H15N5O
C9H16O4

Minoxidil
Nonanedioic acid

C9H18O2
C9H19N
C9H19N

Nonanoic acid
N-Butylpiperidine

C9H21N
C10H7NO2

Step
2
3

2,2,6,6-Tetramethyl piperidine
Nonylamine
8-Quinolinecarboxylic acid

1
2
3

1
2
1
2
1
2
3
1
2
3
4

1
2
1
2
1
2

1
2
3
1
2
3
1
2
1
2

t/C
25
25
25
25

pKa
5.32
9.48
3.62
4.50

25

4.47

25
25
25
25
25
25
25
25

4.48
7.2
2.2
8.7
9.1
6.18
4.32
4.66
4.64
3.47

25
22

25
25
25
25
25
25
25
25
25
25
25
25
25

9.4
4.17
9.21
6.03
11.49
2.5
2.20
9.31
2.20
9.11
10.1
2.32
8.72
9.96
11.79
7.33
5.77
8.66
9.95
6.4
9.5
4.22
12.5
9.44

25
25
25
23
25

8.45
0.8
4.28
6.0
2.73
6.87
9.73
3.7
9.8
4.61
4.53
5.33
4.96
10.47
11.07

25
25

10.64
1.82

20
20
20

8-49
Mol. form.
C10H8O
C10H8O
C10H9N
C10H9N
C10H9N
C10H9N
C10H9N
C10H9NO
C10H9NO
C10H9NO2
C10H10O2
C10H10O2
C10H10O2
C10H12N2
C10H12N2O

Name
1-Naphthol
2-Naphthol
1-Naphthylamine
2-Naphthylamine
2-Methylquinoline
4-Methylquinoline
5-Methylquinoline
5-Amino-1-naphthol
6-Methoxyquinoline
1H-Indole-3-acetic acid
o-Methylcinnamic acid
m-Methylcinnamic acid
p-Methylcinnamic acid
Tryptamine
5-Hydroxytryptamine

C10H12N2O5
C10H12N4O3
C10H12O

Dinoseb
Dideoxyinosine

C10H12O2
C10H12O5
C10H13N5O4
C10H14N2

L-Nicotine

C10H14N5O7P

5-Adenylic acid

C10H14O
C10H14O
C10H14O
C10H15N
C10H15N
C10H15NO
C10H15NO
C10H17N3O6S

2-tert-Butylphenol
3-tert-Butylphenol
4-tert-Butylphenol
N-tert-Butylaniline
N,N-Diethylaniline
d-Ephedrine
l-Ephedrine
l-Glutathione

C10H18N4O5

L-Argininosuccinic acid

C10H18O4

Sebacic acid

C10H19N
C10H19N
C10H21N
C10H21N

Bornylamine
Neobornylamine
Butylcyclohexylamine

C11H8O2
C11H11N
C11H12I3NO2
C11H12N2O2

1
2

1
2
1
2
1
2

1
2
3
4
1
2
3
4
1
2

1,2,2,6,6-Pentamethyl piperidine
Decylamine
1H-Perimidine
1-Naphthalenecarboxylic
acid
2-Naphthalenecarboxylic
acid
Methyl-1-naphthylamine
Iopanoic acid
L-Tryptophan

t/C
25
25
25
25
20
20
20
25
20
25
25
25
25
25
25

25

5,6,7,8-Tetrahydro-2 naphthalenol
Benzenebutanoic acid
Propyl 3,4,5-trihydroxy benzoate
Adenosine

C10H23N
C11H8N2
C11H8O2

Step

1
2

pKa
9.39
9.63
3.92
4.16
5.83
5.67
5.20
3.97
5.03
4.75
4.50
4.44
4.56
10.2
9.8
11.1
4.62
9.12
10.48

25

4.76
8.11

25
25

25
25
25
30

3.6
12.4
8.02
3.12
3.8
6.2
10.62
10.12
10.23
7.00
6.57
10.139
9.958
2.12
3.59
8.75
9.65
1.62
2.70
4.26
9.58
4.59
5.59
10.17
10.01
11.23
11.25

25
20
25

10.64
6.35
3.69

25

4.16

27

3.67
4.8
2.46
9.41

25
25
25
25
25
10
10
25
25
25
25
25
25
25
25

25
25

Dissociation Constants of Organic Acids and Bases

8-50
Mol. form.
C11H12N4O3S
C11H13F3N2O3S
C11H13NO3
C11H13N3O3S
C11H14N2O

Name
Sulfamethoxypyridazine
Mefluidide
Hydrastinine
Sulfisoxazole
Cytisine

C11H14O2
C11H14O2
C11H14O2
C11H16N2O2

2-tert-Butylbenzoic acid
3-tert-Butylbenzoic acid
4-tert-Butylbenzoic acid
Pilocarpine

C11H16N4O4
C11H17N

Pentostatin

C11H17NO3
C11H17N3O8
C11H18ClNO3
C11H18N2O3
C11H25N
C11H26NO2PS
C12H6Cl4O2S
C12H8N2
C12H8N2
C12H10O
C12H10O
C12H10O
C12H11N
C12H11N
C12H11N
C12H11N
C12H11N
C12H11N3
C12H12N2

1,10-Phenanthroline
Phenazine
2-Hydroxybiphenyl
3-Hydroxybiphenyl
4-Hydroxybiphenyl
Diphenylamine
2-Aminobiphenyl
3-Aminobiphenyl
4-Aminobiphenyl
2-Benzylpyridine
4-Aminoazobenzene
p-Benzidine

C12H12N2O3

Phenobarbital

C12H13N

1
2

1
2

Iocetamic acid

C12H14N4O2S
C12H14N4O3S
C12H17N3O4

Sulfacytine
Agaritine

C12H20N2O2
C12H21N5O2S2

Aspergillic acid
Nizatidine

C12H22O11
C12H22O11
C12H23N
C12H27N
C13H9N
C13H9N
C13H10N2
C13H10N2

Sucrose
-Maltose
Dicyclohexylamine
Dodecylamine
Acridine
Phenanthridine
9-Acridinamine
2-Phenylbenzimidazole

25
25
25
25
25

25
25
25

1
2

1
2
1
2

25
20
25
25
25
25
25
18
18
25
25
20
20

25

N,N-Dimethyl-1 naphthylamine
N,N-Dimethyl-2 naphthylamine
Sulfamethazine

t/C

25

N,N-Diethyl-2-methyl aniline
Isoproterenol
Tetrodotoxin
Methoxamine hydrochloride
Amobarbital
Undecylamine
Methylphosphonothioic acid
S[2-[bis(1-isopropyl)amino] ethyl], O-ethylester
Bithionol

C12H13I3N2O3
C12H13N

Step

25
1
2
1
2
1
2

1
2

25
21
25
20
20
20
25
25

pKa
6.7
4.6
11.38
5
6.11
13.08
3.54
4.20
4.38
1.6
6.9
5.2
7.24
8.64
8.76
9.2
8.0
10.63
7.9

4.82
10.50
4.84
1.20
10.01
9.64
9.55
0.79
3.83
4.25
4.35
5.13
2.82
4.65
3.43
7.3
11.8
4
4.83
4.566
7.4
2.65
6.9
3.4
8.86
5.5
2.1
6.8
12.7
12.05
10.4
10.63
5.58
5.58
9.99
5.23
11.91

Mol. form.
C13H10O2
C13H10O3
C13H10O3
C13H10O3
C13H11N3
C13H12Cl2O4
C13H12N2O
C13H12N2O3S
C13H13N
C13H14N2O13
C13H15N3O3
C13H16ClNO
C13H19NO4S
C13H21N
C13H29N
C14H12F3NO4S2
C14H12O2
C14H12O3

Name
2-Phenylbenzoic acid
2-Phenoxybenzoic acid
3-Phenoxybenzoic acid
4-Phenoxybenzoic acid
3,6-Acridinediamine
Ethacrynic acid
Harmine
Sulfabenzamide
4-Benzylaniline
Harmaline
Imazapyr
Ketamine

Step

25
25
1
2

4-[(Dipropylamino) sulfonyl]benzoic acid

2,6-Di-tert-butylpyridine
(Tridecyl)amine
Perfluidone
-Phenylbenzeneacetic acid

C14H18N4O3
C14H19NO2
C14H21N3O3S
C14H22N2O3
C14H31N
C15H10ClN3O3

-Hydroxy--phenyl benezeneacetic acid

Trimethoprim
Methylphenidate
Tolazamide
Atenolol
Tetradecylamine
Clonazepam

C15H11I4NO4

L-Thyroxine

C15H14O3
C15H15NO2
C15H15N3O2

Fenoprofen
Mefenamic acid
Methyl Red

C15H17ClN4
C15H19NO2
C15H19N3O3

NeutralRed
Tropacocaine
Imazethapyr

C15H21N3O2

Physostigmine

C15H26N2

Sparteine

C15H33N
C16H13ClN2O
C16H14ClN3O
C16H16N2O2

Pentadecylamine
Valium
Chlorodiazepoxide
Lysergic acid

C16H17N3O4S

Cephalexin

C16H19N3O4S

Cephradine

C16H22N2

Lycodine

C16H35N
C17H17NO2

Hexadecylamine
Apomorphine

C17H19NO3
C17H19NO3

Piperine
Morphine

C17H20N4O6

Riboflavin

t/C
25
25
25
25
20

25
25
25

25

1
2
1
2
3

25

25
25
25

1
2

1
2
1
2
1
2

1
2
1
2
1
2
1
2
1
2
1
2
1

15

20
20
25

25

18
25
20

pKa
3.46
3.53
3.95
4.57
9.65
3.50
7.70
4.57
2.17
4.2
1.9
3.6
7.5
5.8
3.58
10.63
2.5
3.94
3.04
6.6
8.9
3.6
9.6
10.62
1.5
10.5
2.2
6.45
10.1
4.5
4.2
2.5
9.5
6.7
4.32
2.1
3.9
6.12
12.24
2.24
9.46
10.61
3.4
4.8
3.44
7.68
5.2
7.3
2.63
7.27
3.97
8.08
10.61
7.0
8.92
12.22
8.21
9.85
1.7

Dissociation Constants of Organic Acids and Bases

Mol. form.

Name

C17H20O6
C17H23NO3
C17H27NO4
C18H19ClN4

Mycophenolic acid
Hyoscyamine
Nadolol
Clozapine

C18H21NO3
C18H21N3O
C18H32O2
C18H33ClN2O5S
C18H39N
C19H10Br4O5S
C19H14O5S
C19H16ClNO4
C19H17N3O4S2
C19H20N2O2
C19H21N
C19H21NO3
C19H22N2O

Codeine
Dibenzepin
Linoleic acid
Clindamycin
Octadecylamine
Bromophenol Blue
Phenol Red
Indomethacin
Cephaloridine
Phenylbutazone
Protriptyline
Thebaine
Cinchonine

C19H22N2O

Cinchonidine

C19H22N2O2
C19H22O6
C19H23N3O2
C19H23N3O2
C20H14O4
C20H21NO4
C20H23N
C20H23N7O7

Cupreine
Gibberellic acid
Ergometrinine
Ergonovine
Phenolphthalein
Papaverine
Amitriptyline
Folinic acid

C20H24N2O2

Quinine

C20H24N2O2

Quinidine

C20H26N2O2
C21H14Br4O5S
C21H16Br2O5S
C21H18O5S
C21H21NO6
C21H22N2O2

Hydroquinine
Bromocresol Green
Bromocresol Purple
CresolRed
Hydrastine
Strychnine

Step
2

t/C
25
21

1
2

25
25

1
2
1
2

15

25

1
2
3
1
2
1
2

25
25
20
20

25

pKa
9.69
4.5
9.7
9.67
3.70
7.60
8.21
8.25
4.77
7.6
10.60
4.0
7.9
4.5
3.2
4.5
8.2
6.05
5.85
9.92
5.80
10.03
6.57
4.0
7.3
6.8
9.7
6.4
9.4
3.1
4.8
10.4
8.52
4.13
5.4
10.0
5.33
4.7
6.3
8.3
7.8
8.26

8-51
Mol. form.
C21H23ClFNO2
C21H31NO4
C21H35N3O7

Name
Haloperidol
Furethidine
Lisinopril

C22H18O4
C22H22FN3O2
C22H23NO7
C22H25NO6
C22H25N3O

o-Cresolphthalein
Droperidol
Noscapine
Colchicine
Benzpiperylon

C22H33NO2
C23H26N2O4

Atisine
Brucine

C24H40O4
C24H40O5
C25H29I2NO3
C25H41NO9
C26H43NO6
C26H45NO7S
C27H28Br2O5S
C27H38N2O4
C29H32O13
C29H40N2O4

Deoxycholic acid
Cholic acid
Amiodarone
Aconine
Glycocholic acid
Taurocholic acid
Bromothymol Blue
Verapamil
Etoposide
Emetine

C30H23BrO4
C30H48O3
C31H36N2O11

Bromadiolone
Oleanolic acid
Novobiocin

C32H32O13S
C33H40N2O9
C34H47NO11
C36H51NO11
C37H67NO13
C43H58N4O12

Teniposide
Reserpine
Aconitine
Veratridine
Erythromycin
Rifampin

C45H73NO15
C46H56N4O10
C46H58N4O9

Solanine
Vincristine
Vinblastine

Step

t/C

1
2
3
4

1
2
1
2

1
2

20

20
20
25

21

1
2

1
2

1
2

15

pKa
8.3
7.48
2.5
4.0
6.7
10.1
9.4
7.64
7.8
12.36
6.73
9.13
12.2
6.04
11.07
5.15
4.98
6.56
9.52
4.4
1.4
7.0
8.6
9.8
5.77
6.64
4.04
2.52
4.3
9.1
10.13
6.6
5.88
9.54
8.8
1.7
7.9
6.66
5.4
5.4
7.4