PKa Values INDEX - Organic Chemistry Data

Provided by the ACS, Organic Division

pKa Data Compiled by R. Williams

pKa Values INDEX

Updated 4/7/2022 Page 1

Inorganic Phosphates Carboxylic acids

Aliphatic Aromatic Phenols Alcohols and oxygen acids Amino Acids Peptides Nitrogen Compounds Aliphatic amines Cyanoamines Anilines Nucleosides Special Table Heterocycles Acridine Benzoquinoline Cinnoline Hydantoin Imidazole

2 3 4, 8 4, 8 7, 8 9 10, 11 12 13 14 15, 17, 19 16 17, 18, 20 21 22 23 24 23 24 24

Phenazine Pyridine Pyrazine

Quinoline Quinazoline Quinoxaline Special Nitrogen Compounds Hydroxylamines Hydrazines Semicarbazones Amidoximes Thiols Carbon Acids Indicators References

For complex chelating agents, see also reference 77.

24 25 26

27 27 27 28 28 28 28 28 29 30,31 31 32-34

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

Provided by the ACS, Organic Division

pKa Data Compiled by R. Williams

ACIDS Compound

AgOH

Al(OH)3 As(OH)3 H3AsO4 H2AsO4? HAsO 4 * As 2 O3 H3AsO3 H3BO3 H2B4O7 HB4O7 Be(OH) 2 HBr

HOBr

HOCl

HClO2 HClO3 HClO4 (70%) CH3SO3H HCN

H2CO3 HCO3 H2CrO4 HCrO4 HOCN

HZ

H2GeO3 Ge(OH)4 HI

HOI

HIO3 H4IO6? H5IO6 HMnO4 NH3OH* NH4* HN3 HNO2 HNO3 N2H5+ H2N2O2 H2N2O2? H2OsO5 H2O H3O+ Pb(OH)2

pK

Ref.

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 14.0* 0* 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 97 97 4 (78)

Updated 4/7/2022 Page 2

H3PO2 H2PO4? HPO4_ H3PO3 H2PO3? H4P2O7 H3 P2O7? H2P2O7= HP2O7= HReO4 HSCN

H2SeO3 HSeO3 H2SeO4 HSeO4 H3SiO3 H2SO3 H2SO4 HSO3 HSO4? H2S2O4 H2Se HSe?

H2S HS?

HSbO2 HTe

H2Te H2TeO3 Te(OH) 6 H2VO4? HVO4= H2CrO4 HOCN

HSCN

H3PO2 H3PO4 H2S2O3 H3AuO3 H3GaO3 H5IO6

H4V6O17 H2NSO3H

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

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

* Indicates a thermodynamic value.

Provided by the ACS, Organic Division

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

Methyl-

1.54, 6.31

Ethyl-

1.60, 6.62

n-Propyl-

1.88,6.67

n-Butyl-

1.80, 6.84

Dimethyl-

1.29

Di-n-propyl

1.59

Di-n-butyl-

1.72

Glucose-3-

0.84, 5.67

Glucose-4-

0.84, 5.67

-glycero-

1.40, 6.44

-glycero-

1.37, 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

glyceraldehyde-

2.10, 6.75

dioxyacetone-

1.77,6.45

hexose di-

1.52, 6.31

fructose-6-

0.97, 6.11

glucose-6-

0.94, 6.11

glucose-1-

1.10, 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

H2O3P(CH2)4PO3H2 ................
................

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