Journal of Computer-Aided Molecular Design

, Volume 28, Issue 10, pp 1031–1034 | Cite as

The IUPAC aqueous and non-aqueous experimental pKa data repositories of organic acids and bases

  • Anthony Michael Slater


Accurate and well-curated experimental pKa data of organic acids and bases in both aqueous and non-aqueous media are invaluable in many areas of chemical research, including pharmaceutical, agrochemical, specialty chemical and property prediction research. In pharmaceutical research, pKa data are relevant in ligand design, protein binding, absorption, distribution, metabolism, elimination as well as solubility and dissolution rate. The pKa data compilations of the International Union of Pure and Applied Chemistry, originally in book form, have been carefully converted into computer-readable form, with value being added in the process, in the form of ionisation assignments and tautomer enumeration. These compilations offer a broad range of chemistry in both aqueous and non-aqueous media and the experimental conditions and original reference for all pKa determinations are supplied. The statistics for these compilations are presented and the utility of the computer-readable form of these compilations is examined in comparison to other pKa compilations. Finally, information is provided about how to access these databases.


IUPAC pKa Database Aqueous pKa Non-aqueous pKa Organic acid Organic base pKa database pKa compilation pKa repository Experimental pKa 



The author would like to thank Peter Kenny, Andrew Grant, David Cosgrove, Thorsten Nowak, Anthony Nicholls, Joe Corkery, Huw Jones, Martin Harrison, Nicola Colclough, Philip Jewsbury, Andrew Poirrette, Neil Hales and Sandra McLaughlin for discussions, help and encouragement before and during the conversion of the IUPAC books into computer-readable form.


  1. 1.
    Aqueous pKa compilation by Williams R (document compiled by Jencks WP, added to by Westheimer FH). Accessed 11 Mar 2014
  2. 2.
    Aqueous pKa compilation with some dimethyl sulfoxide values by Ripin DH, Evans DA. Accessed 11 Mar 2014
  3. 3.
    pKa values in dimethyl sulfoxide compilation by Bordwell FG. Accessed 12 Mar 2014
  4. 4.
    Links to tables of pKa values in non-aqueous solvents taken from literature by Leito I. Accessed 12 Mar 2014
  5. 5.
    Albert A (1963) Ionization constants of heterocyclic substances. In: Katritzky AR (ed) Physical methods in heterocyclic chemistry. Academic Press, New YorkGoogle Scholar
  6. 6.
    Ritschel WA (1972) pKa values and some clinical applications. In: Francke D, Whitney H (eds) Perspectives in clinical pharmacy, 1st edn. Drug Intelligence Publications, Hamilton, pp 325–367Google Scholar
  7. 7.
    Smith S, Rawlins M (1973) Appendix C. Variability in human drug response, 1st edn. Butterworths, London, pp 154–165Google Scholar
  8. 8.
    Speight T (1987) Avery’s drug treatment, 3rd edn. Publishing Sciences Group Inc, Littleton, pp 1352–1380Google Scholar
  9. 9.
    Hoover J (1976) In: Dispensing of Medication, 8th edn. Mack Publishing, Easton, PA, p. 230, 247, 418–426, 468–634.Google Scholar
  10. 10.
    Newton D, Kluza R (1978) pKa values of medicinal compounds in pharmacy practice. Drug Intell Clin Pharm 12:546–554Google Scholar
  11. 11.
    Craig P (1990) In: Hansch C, Sammes P, Taylor J (eds) Compendium of drugs, in comprehensive medicinal chemistry, 1st edn. Pergamon Press, New York, pp 237–965Google Scholar
  12. 12.
    Williams D (1995) Appendix A-1. In: Foye W, Lemke T, Williams D (eds) Principles of medicinal chemistry, 4th edn. Williams and Wilkins, Baltimore, pp 948–961Google Scholar
  13. 13.
    Delgado J, Remers W (2000) pKas of drugs and reference compounds. In: Delgado J, Remers W (eds) Wilson and Gisvold’s textbook of organic medicinal and pharmaceutical chemistry, 8th edn. Lippincott-Raven, PhiladelphiaGoogle Scholar
  14. 14.
    Prankerd RJ (2007) In: Brittain HG (ed) Profiles of drug substances, excipients and related methodology volume 33, 1st edn. Academic Press, LondonGoogle Scholar
  15. 15.
    Liao C, Nicklaus M (2009) Comparison of nine programs predicting pKa values of pharmaceutical substances. J Chem Inf Model 49:2801–2812CrossRefGoogle Scholar
  16. 16.
    Manchester J, Walkup G, Rivin O, You Z (2010) Evaluation of pKa estimation methods on 211 druglike compounds. J Chem Inf Model 50:565–571CrossRefGoogle Scholar
  17. 17.
    Cox BG (2013) Acids and bases solvent effects on acid–base strength, 1st edn. Oxford University Press, OxfordCrossRefGoogle Scholar
  18. 18.
    Perrin DD (1965) Dissociation constants of organic bases in aqueous solution, 1st edn. Butterworths, LondonGoogle Scholar
  19. 19.
    Perrin DD (1972) Dissociation constants of organic bases in aqueous solution, supplement, 1st edn. Butterworths, LondonGoogle Scholar
  20. 20.
    Kortum G, Vogel W, Andrussow K (1961) Dissociation constants of organic acids in aqueous solution, 1st edn. Butterworths, LondonGoogle Scholar
  21. 21.
    Serjeant E, Dempsey B (1979) Ionisation constants of organic acids in aqueous solution, 1st edn. Pergamon Press, OxfordGoogle Scholar
  22. 22.
    Izutsu K (1990) Acid–base dissociation constants in dipolar aprotic solvents, 1st edn. Blackwell Scientific Publications, OxfordGoogle Scholar
  23. 23.
    IUPAC books of experimental pKa values of organic acids and bases in both aqueous and non-aqueous solvents as searchable pKa databases by Slater AM. Accessed 13 March 2014
  24. 24.
    SMILES—A Simplified Chemical Language. Accessed 14 March 2014
  25. 25.
    Tautomer enumeration using QuacPac by OpenEye Scientific Software. Accessed 14 March 2014
  26. 26.
    Partition coefficient definition. Accessed 14 March 2014
  27. 27.
    Bandura AV, Lvov SN (2006) The ionization constant of water over a wide range of temperatures and densities. J Phys Chem Ref Data 35:15–30CrossRefGoogle Scholar
  28. 28.
    ACD Labs internal pKa database. Accessed 14 March 2014
  29. 29.
    BioByte raw data. Accessed 14 March 2014
  30. 30.
    pKa Prospector, search software from OpenEye Scientific Software. Accessed 14 March 2014

Copyright information

© Springer International Publishing Switzerland 2014

Authors and Affiliations

  1. 1.pKaData LimitedReephamUK

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