Skip to main content
Log in

Complex formation of zinc-containing metalloporphyrins and nucleophilic substitution reactions involving pyridines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Linear correlations were found between the thermodynamic and kinetic parameters for the nucleophilic substitution and coordination of metalloporphyrins in various solvents with the participation of pyridines. Complex formation of zinc(II) tetraphenylporphyrin with n-donor ligands in chloroform at 25°C is proposed for use as a model system in the electronic spectroscopic investigation of the nucleophilicity and basicity of compounds capable of forming complexes of the n,ν type.

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

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. V. P. Andreev, Ya. P. Nizhnik, D. G. Bezruchko, and A. K. Morozov, Zh. Obshch. Khim., 75, 1379 (2005).

    Google Scholar 

  2. V. P. Andreev, V. V. Vapirov, Ya. P. Nizhnik, S. G. Tunina, and P. S. Sobolev, Zh. Org. Khim., 46, 1556 (2010).

    Google Scholar 

  3. V. P. Andreev, Diss. Doct. Chem. Sci. [in Russian], Petrozavodsk (2007).

  4. V. P. Andreev, Ya. P. Nizhnik, and N. Sh. Lebedeva, Zh. Org. Khim., 44, 1201 (2008).

    Google Scholar 

  5. К. М. Kadish and L. R. Shiue, Inorg. Chem., 21, 3623 (1982).

    Article  CAS  Google Scholar 

  6. G. Szintay and A. Horvath, Inorg. Chim. Acta, 310, 175 (2000).

    Article  CAS  Google Scholar 

  7. S. W. Hong, H. J. Koh, and I. Lee, J. Phys. Org. Chem., 12, 425 (1999).

    Article  CAS  Google Scholar 

  8. С. Castro and E. A. Castro, J. Org. Chem., 46, 2939 (1981).

    Article  CAS  Google Scholar 

  9. W. J. Spillane, G. Hogan, P. McGrath, J. King, and С. Brack, J. Chem. Soc., Perkin Trans. 2, 2099 (1996).

  10. A. Fischer, W. J. Galloway, and J. Vaughan, J. Chem. Soc., 3591 (1964).

  11. E. M. Arnett and R. Reich, J. Am. Chem. Soc., 102, 5892 (1980).

    Article  CAS  Google Scholar 

  12. O. Rogne, J. Chem. Soc. B, 727 (1970).

  13. V. A. Savelova, A. F. Popov, T. N. Solomoichenko, Yu. S. Sadovskii, Zh. P. Piskunova, and O. V. Lobanova, Zh. Org. Khim., 36, 1502 (2000).

    Google Scholar 

  14. V. A. Savelova, T. N. Solomoichenko, T. V. Ved', Yu. S. Sadovskii, and Yu. S. Simanenko, Zh. Org. Khim., 29, 666 (1993).

    CAS  Google Scholar 

  15. D. Herschlag and W. P. Jenks, J. Am. Chem. Soc., 112, 1951 (1990).

    Article  CAS  Google Scholar 

  16. V. P. Andreev, P. S. Sobolev, D. O. Zaitsev, N. A. Galibina, N. S. Zykina, L. Yu. Plyasunova, and M. I. Romanova, Uch. Zap. PetrGU, Ser. Estestv. i Tekhn. Nauki, No. 6 (119), 7 (2011).

  17. K. M. Kadish, L. R. Shiue, R. K. Rhodes, and L. A. Bottomley, Inorg. Chem., 20, 1274 (1981).

    Article  CAS  Google Scholar 

  18. R. G. Garvey, J. H. Nelson, and R. O. Ragsdale, Coord. Chem. Rev., 3, 375 (1968).

    Article  CAS  Google Scholar 

  19. H. Becker, Introduction to Electronic Theory of Organic Reactions [Russian translation], Mir, Moscow 1977.

    Google Scholar 

  20. R. W. Hoffmann, Mechanisms of Organic Reactions [Russian translation], Khimiya, Moscow (1979).

    Google Scholar 

  21. L. J. Andrews and R. M. Keefer, Molecular Complexes in Organic Chemistry, Holden-Day, San Francisco (1964).

    Google Scholar 

  22. I. R. Bellobono and M. A. Monetti, J. Chem. Soc., Perkin Trans. 2, 790 (1973).

  23. B. P. Nikol’skii (editor), Physical Chemistry. Theoretical and Practical Handbook. Textbook for Universities [in Russian], Khimiya, Leningrad (1987).

    Google Scholar 

  24. J. E. Falk, Porphyrins and Metaloporphyrins, Vol. 2, Elsevier, Amsterdam-London-New York (1964), p. 266.

    Google Scholar 

  25. A. S. Brandis, A. N. Kozyrev, and A. F. Mironov, Tetrahedron, 48, 6485 (1992).

    Article  CAS  Google Scholar 

  26. S. Lötjönen and P. H. Hynninen, Synthesis, 541 (1980).

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. P. Andreev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 529-537, March, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Andreev, V.P., Sobolev, P.S., Larkina, E.A. et al. Complex formation of zinc-containing metalloporphyrins and nucleophilic substitution reactions involving pyridines. Chem Heterocycl Comp 48, 497–504 (2012). https://doi.org/10.1007/s10593-012-1022-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-1022-2

Keywords

Navigation