Skip to main content
SpringerLink
Log in

Calculations of dissociation constants of carboxylic acids by empirical and quantum-chemical DFT methods

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Dissociation constants of 15 carboxylic acids in water, methanol, and DMSO were calculated by empirical and quantum-chemical DFT methods. The maximal error of the empirical calculation was 1.4%. A comparative analysis of the results obtained was carried out.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Kong, X., Zhou, T., Liu, Z., and Hider, R.C., J. Pharm. Sci., vol. 96, no. 10, p. 2777.

  2. Box, K., Bevan, C., Comer, J., Hill, A., Allen, R., and Reynolds, D., Anal. Chem., 2003, vol. 75, no. 4, p. 883.

    Article  CAS  Google Scholar 

  3. Jover, J., Bosque, R., and Sales, J., QSAR Comb. Sci., 2007, vol. 26, no. 3, p. 385.

    Article  CAS  Google Scholar 

  4. Jover, J., Bosque, R., and Sales, J., QSAR Comb. Sci., 2008, vol. 27, no. 4, p. 563.

    Article  CAS  Google Scholar 

  5. Jover, J., Bosque, R., and Sales, J., QSAR Comb. Sci., 2008, vol. 27, no. 10, p. 1179.

    Article  CAS  Google Scholar 

  6. Ghasemi, J., Saaidpour, S., and Brown, S.D., J. Struct. Chem. THEOCHEM., 2007, vol. 805, nos. 1–3, p. 27.

    Article  CAS  Google Scholar 

  7. Zhang, J., Kleinoeder, T., and Gasteiger, J., J. Chem. Inf. Model., 2006, vol. 46, no. 6, p. 2256.

    Article  CAS  Google Scholar 

  8. Gieleciak, R. and Polanski, J., J. Chem. Inf. Model., 2007, vol. 47, no. 2, p. 547.

    Article  CAS  Google Scholar 

  9. Ivanova, A.A., Baskin, I.I., Palyulin, V.A., and Zefirov, N.S., Dokl. Akad. Nauk, 2007, vol. 413, no. 6, p. 766.

    Google Scholar 

  10. Habibi-Yangjeh, A. and Danandeh-Jenagharad, M., Ind. J. Chem., Section B: Organic Chemistry Including Medicinal Chemistry, 2007, vol. 46, no. 3, p. 478.

    Google Scholar 

  11. Carabias-Martınez, R., Rodrıguez-Gonzalo, E., Domınguez-Alvarez, J., and Miranda-Cruz, E., Anal. Chim. Acta., 2007, vol. 584, no. 2, p. 410.

    Article  CAS  Google Scholar 

  12. Jelfs, S., Ertl, P., and Selzer, P., J. Chem. Inf. Model., 2007, vol. 47, no. 2, p. 450.

    Article  CAS  Google Scholar 

  13. Milletti, F., Storchi, L., Sforna, G., and Cruciani, G., J. Chem. Inf. Model., 2007, vol. 47, no. 6, p. 2172.

    Article  CAS  Google Scholar 

  14. Popelier, P.L.A. and Smith, P.J., Eur. J. Med. Chem., 2006, vol. 41, no. 7, p. 862.

    Article  CAS  Google Scholar 

  15. Shan, X., Qin, W., Zhou, Z., and Dai, Y., J. Chem. Eng. Data, 2008, vol. 53, no. 2, p. 331.

    Article  CAS  Google Scholar 

  16. Hiromasa, K., Masamoto, A., and Kimito, F., J. Chem. Inf. Model., 2008, vol. 48, no. 3, p. 534.

    Article  CAS  Google Scholar 

  17. Meloun, M. and Bordovska, S., Anal. Bioanal. Chem., 2007, vol. 389, no. 4, p. 1267.

    Article  CAS  Google Scholar 

  18. Esteki, M., Hemmateenejad, B., Khayamian, T., and Mohajeri, A., Chem. Biol. Drug Design, 2007, vol. 70, no. 5, p. 413.

    Article  CAS  Google Scholar 

  19. Vokin, A.I., Shulunova, A.M., Aksameentova, T.N., Bozhenkov, G.V., and Turchaninov, V.K., Zh. Obshch. Khim., 2006, vol. 76, no. 2, p. 311.

    Google Scholar 

  20. Stairs, R.A. and Buncel, E., Can. J. Chem., 2006, vol. 84, no. 11, p. 1580.

    Article  CAS  Google Scholar 

  21. Yanchuk, N.I. and Grod, I.N., Zh. Obshch. Khim., 2006, vol. 76, no. 5, p. 757.

    Google Scholar 

  22. Reddy, S.R. and Manikyamba, P., Indian J. Chem. (A), 2006, vol. 45, no. 8, p. 1844.

    Google Scholar 

  23. Makitra, R.G., Midyana, G.G., and Pal’chikova, E.Ya., Zh. Org. Khim., 2005, vol. 41, no. 7, p. 967.

    Google Scholar 

  24. Lakhdar, S., Westermaier, M., Terrier, F., Goumont, R., Boubaker, T., Ofial, A.R., and Mayr, H., J. Org. Chem., 2006, vol. 71, no. 24, p. 9088.

    Article  CAS  Google Scholar 

  25. Um, I.H., Hwang, S.J., and Buncel, E., J. Org. Chem., 2006, vol. 71, no. 3, p. 915.

    Article  CAS  Google Scholar 

  26. Guven, A., Int. J. Mol. Sci., 2005, vol. 6, no. 11, p. 257.

    Article  CAS  Google Scholar 

  27. Pavlat, P., Hlavac, J., and Bekarek, V., Chem. Listy, 2005, vol. 99, no. 8, p. 585.

    CAS  Google Scholar 

  28. Goumont, R., Magnier, E., Kizilian, E., and Terrier, F., J. Org. Chem., 2003, vol. 68, no. 17, p. 6566.

    Article  CAS  Google Scholar 

  29. Lemp, E., Zanocco, A.L., and Lissi, E.A., Curr. Org. Chem., 2003, vol. 7, no. 9, p. 799.

    Article  CAS  Google Scholar 

  30. Mchedlov-Petrosyan, N.O., Differentsirovanie sily organicheskikh kislot v istinnykh i organizovannykh rastvorakh (Differentiation of the Force of Organic Acids in True and Organized Solutions), Kharkov: Izd. Kharkov. Nat. Univer., 2004.

    Google Scholar 

  31. Adams, D.J., Dyson, P.J., and Tavener, S.J., Chemistry in Alternative Reaction Media, Guildfort: Wiley, 2004.

    Google Scholar 

  32. Reichardt, C., Solvents and Solvent Effects in Organic Chemistry, WeinHeim: WILEY-VCH Verlag GmbH, 2003.

    Google Scholar 

  33. Buncel, E., Stairs, R.A., and Wilson, H., Role of the Solvent in Chemical Reactions, Oxford: University Press, 2003.

    Google Scholar 

  34. Range, K., Riccardi, D., Cui, Q., Elstnerc, M., and York, D.M., Phys. Chem. Chem. Phys., 2005, vol. 7, no. 16, p. 3070.

    Article  CAS  Google Scholar 

  35. Meot-Ner, M., Int. J. Mass Spectrometry, 2003, vol. 227, no. 3, p. 525.

    Article  CAS  Google Scholar 

  36. Gross, K.C., Seybold, P., Peralta-Inga, Z., Murray, J.S., and Politzer, P., J. Org. Chem., 2001, vol. 66, no. 6919.

  37. Fu, Y., Liu, L., Li, R.Q., Liu, R., and Guo, Q.X., J. Am. Chem. Soc., 2004, vol. 126, no. 3, p. 814.

    Article  CAS  Google Scholar 

  38. Chipman, D.M., J. Phys. Chem. (A), 2002, vol. 106, no. 32, p. 7413.

    CAS  Google Scholar 

  39. Murowska, K. and Sadlej-Sosnowska, N., J. Phys. Chem. (A), 2005, vol. 109, no. 25, p. 5590.

    Google Scholar 

  40. Brown, T.N. and Mora-Diez, N., J. Phys. Chem. (B), 2006, vol. 110, no. 18, p. 9270.

    CAS  Google Scholar 

  41. Makowska, J., Makowski, M., and Chmurzynski, L., J. Phys. Chem. (A), 2004, vol. 108, no. 46, p. 10354.

    Article  CAS  Google Scholar 

  42. Brown, T.N. and Mora-Diez, N., J. Phys. Chem. (B), 2006, vol. 110, no. 41, p. 20546.

    CAS  Google Scholar 

  43. Kelly, C.P., Cramer, C.J., and Truhlar, D.G., J. Phys. Chem. (A), 2006, vol. 110, no. 7, p. 2493.

    CAS  Google Scholar 

  44. Saracino, G.A., Improta, R., and Barone, V., Chem. Phys. Lett., 2003, vol. 373, nos. 3–4, p. 411.

    Article  CAS  Google Scholar 

  45. Pal’m, V.A., Osnovy kolichestvennoi teorii khimicheskikh reaktsii (Foundations of the Quantitative Theory of Chemical Reactions), Leningrad: Khimiya, 1977.

    Google Scholar 

  46. Ulander, J. and Broo, A., Int. J. Quant. Chem., 2005, vol. 104, no. 6, p. 866.

    Article  CAS  Google Scholar 

  47. Zevatskii, Yu.E. and Lysova, S.N., Zh. Prikl. Khim., 2006, vol. 79, no. 6, p. 978.

    Google Scholar 

  48. Zevatskii, Yu.E. and Vlasov, E.A., Zh. Obshch. Khim., 2007, vol. 77, no. 2, p. 260.

    Google Scholar 

  49. Zevatskii, Yu.E. and Samojlov, D.V., Zh. Prikl. Khim., 2007, vol. 80, no. 2, p. 230.

    CAS  Google Scholar 

  50. Zevatskii, Yu.E. and Samojlov, D.V., Zh. Org. Khim., 2008, vol. 44, no. 1, p. 59.

    Google Scholar 

  51. Bell, R.P, The Proton in Chemistry, New York: Cornell University Press, 1973.

    Google Scholar 

  52. Schrodinger, L.L.C. and Portland, O.R., Jaguar 7.0N, 2007, 1991–2003.

  53. Miertus, S., Scrocco, E., and Tomasi, J., J. Chem. Phys., 1981, vol. 55, no. 1, p. 117.

    Article  CAS  Google Scholar 

  54. Tomasi, J. and Persico, M., Chem. Rev., 1994, vol. 94, no. 7, p. 2027.

    Article  CAS  Google Scholar 

  55. Cammi, R. and Tomasi, J., J. Comput. Chem., 1995, vol. 16, no. 12, p. 1449.

    Article  CAS  Google Scholar 

  56. Salem, L., Electrons in Chemical Reactions: First Principles, New York, 1982.

  57. Pliego, J.R., Chem. Phys. Letters, 2003, vol. 367, nos. 1–2, p. 145.

    Article  CAS  Google Scholar 

  58. Zevatskii, Yu.E. and Samojlov, D.V., Zh. Org. Khim., 2008, vol. 44, no. 12, p. 1764.

    Google Scholar 

  59. Fialkov, Yu.Ya., Rastvoritel’ kak sredstvo upravleniya khimicheskim protsessom (Solvent as the Means of Controlling the Chemical Process), Leningrad: Khimiya, 1990.

    Google Scholar 

  60. Cherkasov, A.R., Galkin, V.I., and Cherkasov, R.A., Usp. Khim., 1996, vol. 65, no. 8, p. 695.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    Yu. E. Zevatskii, D. V. Samoilov & N. S. Panina

Authors
  1. Yu. E. Zevatskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Samoilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. S. Panina
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu. E. Zevatskii.

Additional information

Original Russian Text © Yu.E. Zevatskii, D.V. Samoilov, N.S. Panina, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 5, pp. 772–780.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zevatskii, Y.E., Samoilov, D.V. & Panina, N.S. Calculations of dissociation constants of carboxylic acids by empirical and quantum-chemical DFT methods. Russ J Gen Chem 79, 944–952 (2009). https://doi.org/10.1134/S1070363209050132

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363209050132

Keywords

Search

Navigation