pKa Values INDEX - 甲南大学

1 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.

2 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 Jencks and has been added to by Westheimer pKa Data Compiled by R. Williams page-2. ACIDS. Compound pK Ref. H3 PO 2 , * 28. H2 PO 4 * 77. AgOH 4. HPO 4 _ * 77. Al(OH)3 28. H3 PO 3 28. As(OH)3 28. H3 AsO 4 , , 28 H2 PO 3 * 77. H4 P 2 O 7 * 77. H2 AsO 4 * 77. HAsO 4 * * 77 H3 P 2 O 7 * 77. As 2 O 3 0 4 H2 P 2 O 7 = * 77. H3 AsO 3 * HP2 O 7 = * 77. H3 BO 3 * 28 HReO4 30.

3 H2 B4 O 7 34 HSCN 34. HB4 O 7 34 H2 SeO3 , , * 28. Be(OH) 2 4 HSeO3 77. HBr 31 H2 SeO4 Strong, 28. HOBr 28 HSeO4 34. HOCl , 28, 33 H3 SiO 3 34. HClO2 28 H2 SO 3 , , * 28, 77. HClO3 28 H2 SO 4 , 28. HClO4 (70%) 31 HSO 3 * 77. CH3 SO 3 H 31 HSO 4 * 77. HCN 34 H2 S2 O 4 29. H2 CO 3 , *, 34, 32 H2 Se * 77. HCO 3 *. HSe * 77. H2 CrO4 30. H2 S * 77. HCrO4 * 2, 30. HOCN 34 HS * 77. HZ *, * 77 HSbO 2 34. H2 GeO3 , 34, 78 HTe 34. Ge(OH)4 , 28 H2 Te , 34, 78. HI 31 H2 TeO 3 , 28. HOI 28 Te(OH) 6 , 28. HIO3 28 H2 VO 4 30. H4 IO6 34 HVO4 = 30. H5 IO6 , , 34, 28 H2 CrO4 77.

4 HMnO4 30 HOCN 77. NH3 OH* * HSCN 77. NH4 * * 77 H3 PO 2 77. HN3 * 77 H3 PO 4 * 77. HNO2 28 H2 S2 O 3 *, * 77. HNO3 28 H3 AuO3 , 78. N2 H5 + * 77 H3 GaO 3 , 78. H2 N2 O 2 34 H5 IO6 , , 78. (see above!). H2 N2 O 2 34 H4 V6 O 17 78. H2 OsO 5 34 H2 NSO 3 H 80. H2 O none H3 O + none * Indicates a thermodynamic value . Pb(OH)2 ( ) 4 (78). PHOSPHATES AND PHOSPHONATES CF 3- , 57. CCl 3- , 57. Phosphates NH 3+CH 2- , 57. Compound pK Ref. ( OOCCH 2) 2NH +CH 2 --, 57. Phosphate , , 55 CHCl 2- , 57. Glyceric acid 2-phosphate , 53 CH 2CI- , 57. Enolpyruvic acid , 53.

5 CH 2Br- , 57. Methyl- , 55. Ethyl- , 55 ( OOCCH 22NH +(CH 2) 2- --, 57. n-Propyl- , 55 CH 2I- , 57. n-Butyl- , 55 NH 3+CH 2CH 2- , 57. Dimethyl- 55 C6H 5CH=CH- , 57. Di-n-propyl 55 HOCH 2- , 57. Di-n-butyl- 55 C6H 5NH 2+(CH 2) 3- , -- 57. Glucose-3- , 56 C6H 5NH(CH 2) 3- --, 57. Glucose-4- , 56. Br(CH 2) 2- , 57. -glycero- , 54. -glycero- , 54 CH 3(CH 2) 5CH(COO )- --, 57. 3-phosphoglyceric acid , 54 C6H 5CH 2- , 57. 2-phosphoglyceric acid , , NH 3+(CH 2) 4)- , 57. peroxymonophosphoric acid 69 NH 3+(CH 2) 5- , 57. diphosphoglyceric acid , 54.

6 NH 3+(CH 2) 10- --, 57. glyceraldehyde- , 54. OOC(CH2) 10- --, 57. dioxyacetone- , 54. hexose di- , 54 (CH 3) 3 SiCH 2- , 57. fructose-6- , 54 C6H 5CH 2- , 57. glucose-6- , 54 (C 6H 5)SC- , 57. glucose-1- , 54. adenylic acid , 54 Arylphosphonic acids inosinic acid , 54 2X-RC6H 3PO3H 2. ADP 2 strong, 54 X R. ATP 3 strong, 54 Cl 4-O 2N , 57. pyrophosphoric acid , , , 54 Br 5-O 2N (a), 57. phosphopyruvic acid , 54 Cl 5-Cl (a), 57. creatine phosphate , 54 Cl H , 57. arginine phosphate , , , 54 Br H , 57. arginine , , 54 Br 5-CH 3 , 57. amino phosphate ( ), , 54.

7 Cl 4-NH 2 --, 57. trimetaphosphate 77. CH 3O 4-O 2N , 57. Phosphonates CH 3O H , 57. H 2O3P(CH 2) 4PO3H 2 <2, , , 57 CH 3O 4-O 2N --, 57. H 2O3P(CH 2) 3PO3H 2 <2, , , 57 HO 4-O 2N , 57. H 2O3 PCH 2CH(CH 3)PO 3H 2 <2, , , 57 O2N H , 57. H 2O3 PCH 2PO3H 2 <2, , , 57 F H , 57. Methyl- 57 I H , 57. Ethyl- 57 NH 2H --, 57. n-propyl- 57 CH 3H , 57. isopropyl- , 57 C6H 5 H (a), 57. n-butyl- , 57 HOOC H , 57. isobutyl- , 57. s-butyl- , 57 **These Values were obtained in 50% ethanol. t-butyl- , 57 (a) The compounds were not sufficiently soluble.

8 Neopentyl- , 57 For graphical plots of a large number of substituted 1,1 Dimethylpropyl- , 57 phosphorus compounds see 83. n-hexyl- , 57. n-dodecyl- --, 57 triphosphate , , 77. CH 3(CH 2) 5CH(COOH)- 1, -- 57 tetrametaphosphate 77. fluorophosphate , 56 Acetic acids, substituted Phosphonates (Ref. 2) H- * 20. X -H -H -NH 3+ -NH 3+ O2N- * 20. X(CH 2)PO 3H 2 +. (CH 3)3N - * 20. X(CH 2) 2PO3H 2 +. (CH 3)2NH - * 20. X(CH 2) 4PO3H 2 +. CH 3NH2 - * 20. X(CH 2) 5PO3 H2 X(CH 2) 6PO2H 2 NH3+- * 20. X(CH 2) 10PO2H 2 CH 3SO2- * 20. Phosphines in acetonitrile, see ref.

9 89. NC- * 20. C 6H5SO2- 20. CARBOXYLIC ACIDS HO2C * 20. Aliphatic C 6H5SO- 20. Compound pK Ref. F- 20. Acetoacetic 6 Cl- * 20. Acetopyruvic , (enol) 6 Br- 20. Aconitic, trans- , 6 Cl2- 20. Betaine 6 F2- 20. Citric , , 6 Br3- 20. Crotonic 6 Cl3- 20. Dihydroxyfumaric 6 F3- ( ) (2) 20. Dethylenediamine- , 6 HONC4 20. tetraacetic , F3C- * 20. Formic * 2. Fumaric , 6 N3- 20. Glyceric 6 I- 20. Glycollic 6 C 6H5O- 20. Glyoxylic 6 C 2H5O2C- 20. Homogentistic 6 C 6H5S- * 20. -keto- -methyl valeric 6 CH 3O- 20. Lactic 6 NCS- 20. Maleic , 6 CH 3CO- * 20.

10 Malic , 6 C 2H5O- 20. Oxaloacetic (trans-enol) 6 n-C 3H7O 20. +(cis-enol) , 6 n-C 4H9O 20. Protocatechuic 6 20. Pyruvic 6 HS- * 20. Tartaric + , 6 i-C3H7O- * 20. + or - , 6 CH 3S- * 20. meso , 6 i-C3H7S- * 20. Vinylacetic 6. C 6H5CH 2S- * 20. C 2H5S- * 20. n-C 3H7S- * 20. n-C 4H9S- * 20. HO- * 20. O3S- 20. (C 6H5)3CS- * 20. C 6H5- * 20. CH 2-CH- * 20. * Indicates thermodynamic Values . Unsaturated acids (25 ). Compound pK ref. Compound pK ref. trans-CH 3-CH=CHCO 2H * 20 H-CH 2CH 2CO2H * 2. cis-CH3-CH=CHCO 2H * 2 H-CH=CHCO 2H * 2. C 6H5-CH 2CH 2CO2H * 2 C 6H5CH 2CH 2CO2H * 2.