Skip to main content
SpringerLink
Log in

Basicity parameter of weak organic bases, derived from thermodynamic parameters of their reactions with (tetraphenylporphyrinato)zinc(II)

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

Abstract

The results of spectral and calorimetric studies of molecular adduct formation of porphyrin metal complexes with a wide series of bases (amines, amides, nitriles, ethers, aldehydes, ketones, alcohols, lactones, azoles, heterocyclic compounds, etc.) in organic solvents were systematized. From the thermodynamic parameters for complex formation of weak organic bases with (tetraphenylporphyrinato)zinc(II), a basicity parameter was derived which takes into account electron-donor and polarization properties of organic molecules, as well as steric coordination effects.

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. White, A., Handler, P., and Smith, E.L., Principles of Biochemistry, New York: McGraw-Hill, 1973, 5th ed.

    Google Scholar 

  2. Marques, H.M., Voster, K., and Egan, T.J., J. Inorg. Biochem., 1996, vol. 64, p. 7.

    CAS  PubMed  Google Scholar 

  3. Hihara, T., Okada, Y., and Morita, Z., Dyes Pigments, 2001, vol. 50, p. 185.

    CAS  Google Scholar 

  4. Woodburn, K., Phadke, A.S., and Morgan, A.R., Bioorg. Med. Chem. Lett., 1993, vol. 3, p. 2017.

    CAS  Google Scholar 

  5. Evstigneeva, R.P., Uspekhi khimii porfirinov (Advances in the Chemistry of Poprhyrins), Golubchikov, O.A., Ed., St. Petersburg: NII Khimii St. Peterb. Gos. Univ., 2001, vol. 3, p. 150.

    Google Scholar 

  6. Ostrovskii, V.A. and Kolodobskii, G.I., Slabye organicheskie osnovaniya (Weak Organic Bases), Leningrad: Leningr. Gos. Univ., 1990, p. 94.

    Google Scholar 

  7. Vodorodnaya svyaz’ (Hydrogen Bond), Sokolov, N.D., Ed., Moscow: Nauka, 1981, p. 50.

    Google Scholar 

  8. Kabachnik, M.I., Usp. Khim., 1979, vol. 48, p. 1523.

    Google Scholar 

  9. Benoit, F. and Harrison, A., J. Am. Chem. Soc., 1977, vol. 99, p. 3980.

    CAS  Google Scholar 

  10. Zielenkiewicz, W., Lebedeva, N.Sh., Antina, E.V., Vyugin, A.I., and Kaminski, M., J. Solution Chem., 1998, vol. 27, p. 879.

    CAS  Google Scholar 

  11. V’yugin, A.I., Antina, E.V., and Berezin, M.B., Dostizheniya i problemy teorii sol’vatatsii: Strukturno-termodinamicheskie aspekty (Advances and Problems in the Solvation Theory. Structural-Thermodynamic Aspects), Abrosimov, V.K., Krestov, Al.G., and Al’per, G.A., Eds., Moscow: Nauka, 1998, p. 208.

    Google Scholar 

  12. Beaupere, D., Segvin, J.P., Uzan, R., and Doucet, J.P., Can. J. Chem., 1976, vol. 54, p. 297.

    CAS  Google Scholar 

  13. Hopkinson, A.C. and Czizmadia, I.G., Can. J. Chem., 1974, vol. 52, p. 546.

    CAS  Google Scholar 

  14. Bursey, M.N., Greenberg, R.S., and Pedersen, L.C., Chem. Phys. Lett., 1975, vol. 36, p. 470.

    CAS  Google Scholar 

  15. Marcuss, Y., J. Solution Chem., 1984, vol. 13, p. 599.

    Google Scholar 

  16. Lebedeva, N.Sh., Vyugin, A.I., Pavlycheva, N.A., Parfenyk, E.V., and Davidova, O.I., Thermochim. Acta, 2002, vol. 390, p. 179.

    CAS  Google Scholar 

  17. Lebedeva, N.Sh., V’yugin, A.I., and Pavlycheva, N.A., Zh. Fiz. Khim., 2002, vol. 76, p. 1735.

    CAS  Google Scholar 

  18. Renge, I., Chem. Phys. Lett., 1991, vol. 185, p. 231.

    CAS  Google Scholar 

  19. Kolling, O.W., Anal. Chem., 1978, vol. 50, p. 1581.

    CAS  Google Scholar 

  20. Kosower, E.M., J. Am. Chem. Soc., 1952, vol. 80, p. 3253.

    Google Scholar 

  21. Berezin, B.D. and Enikolopyan, N.S., Porfiriny: struktura, svoistva, sintez (Porphyrins: Structure, Properties, and Synthesis), Moscow: Nauka, 1985, p. 23.

    Google Scholar 

  22. Berezin, B.D., Koordinatsionnye soedineniya porfirinov i ftalocyanina (Coordination Compounds of Porphyrins and Phthalocyanine), Moscow: Nauka, 1976, p. 210.

    Google Scholar 

  23. Imai, N., J. Am. Chem. Soc., 1992, vol. 114, p. 6719.

    CAS  Google Scholar 

  24. Nakamura, M., Bull. Chem. Soc. Jpn., 1995, vol. 68, p. 197.

    CAS  Google Scholar 

  25. Mizayani, T., Ema, T., and Yoshida, T., Inorg. Chem., 1993, vol. 32, p. 2072.

    Google Scholar 

  26. Yamamoto, Y., Nanai, N., Chujo, R., and Inoue, I., Bull. Chem. Soc. Jpn., 1991, vol. 64, p. 3199.

    CAS  Google Scholar 

  27. Ohkubo, K., Tsuchihachi, T., and Yoshida, T., Bull. Chem. Soc. Jpn., 1976, vol. 49, p. 480.

    CAS  Google Scholar 

  28. Atkins, P.W., Quanta: A Handbook of Concepts, Oxford: Clarendon, 1974. Translated under the title Kvanty, Moscow: Mir, 1977, p. 124.

    Google Scholar 

  29. Uno, T. and Kyuno, E., Inorg. Chem., 1990, vol. 29, p. 2416.

    Google Scholar 

  30. Lebedeva, N.Sh., Mikhailovskii, K.V., V’yugin, A.I., and Davydova, O.I., Zh. Fiz. Khim., 2002, vol. 76, p. 1145.

    CAS  Google Scholar 

  31. Lebedeva, N.Sh., V’yugin, A.I., and Pavlycheva, N.A., Zh. Fiz. Khim., 2002, vol. 76, p. 1334.

    CAS  Google Scholar 

  32. Lebedeva, N.Sh., Pavlycheva, N.A., and V’yugin, A.I., Zh. Fiz. Khim., 2003, vol. 77, p. 426.

    CAS  Google Scholar 

  33. Drago, R.S., Vogel, G.C., and Needham, T.E., J. Am. Chem. Soc., 1971, vol. 93, p. 6014.

    CAS  Google Scholar 

  34. Vogel, G.C. and Searby, L.A., Inorg. Chem., 1973, vol. 12, p. 936.

    CAS  Google Scholar 

  35. Vogel, G.C. and Stahlbush, J.R., Inorg. Chem., 1977, vol. 16, p. 1977.

    Google Scholar 

  36. Gur’yanova, E.N., Gol’dshtein, I.P., and Romm, I.P., Donorno-aktseptornaya svyaz’ (The Donor-Acceptor Bond), Moscow: Khimiya, 1973, p. 102.

    Google Scholar 

  37. Bergmann, E.D., Molecular Associations in Biology, Pullman, B., Ed., New York: Academic, 1968, p. 40.

    Google Scholar 

  38. Sidorov, A.N., Biofizika, 1974, vol. 19, p. 45.

    CAS  PubMed  Google Scholar 

  39. Gasco, M.R., Farmacia, 1976, vol. 31, p. 308.

    CAS  Google Scholar 

  40. Lebedeva, N.Sh., V’yugin, A.I., and Pavlycheva, N.A., Zh. Fiz. Khim., 2003, vol. 77, p. 3.

    Google Scholar 

  41. Lebedeva, N.Sh., Mikhailovskii, K.V., and V’yugin, A.I., Russ. J. Gen. Chem., 2003, vol. 73, p. 3.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Solution Chemistry, Russian Academy of Sciences, ul. Akademicheskaya 1, Ivanovo, 153045, Russia

    N. Sh. Lebedeva, N. A. Pavlycheva & A. I. V’yugin

Authors
  1. N. Sh. Lebedeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. A. Pavlycheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. I. V’yugin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 12, 2004, pp. 1776–1786.

Original Russian Text Copyright © 2004 by Lebedeva, Pavlycheva, V’yugin.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lebedeva, N.S., Pavlycheva, N.A. & V’yugin, A.I. Basicity parameter of weak organic bases, derived from thermodynamic parameters of their reactions with (tetraphenylporphyrinato)zinc(II). Russ J Org Chem 40, 1727–1736 (2004). https://doi.org/10.1007/s11178-005-0090-5

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11178-005-0090-5

Keywords

Search

Navigation