Skip to main content
SpringerLink
Log in

Effect of imidazole on the structure and properties of Zn-5,15-di(o-methoxyphenyl)-2,8,12,18-tetramethyl-3,7,13,17-tetrabutylporphyrin in reaction with organic peroxides

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

Abstract

The reaction of Zn-5,15-di(o-methoxyphenyl)-2,8,12,18-tetramethyl-3,7,13,17-tetrabutylporphyrin with organic peroxides in the presence of imidazole was studied in order to investigate the effect of modification and deformation of the macrocycle on the redox properties of metalloporphyrins. The kinetic characteristics of the reaction were obtained. It was found that the introduction of imidazole into the reaction mixture resulted in an increase in the rate of oxidation of zincporphyrin. Quantum-chemical calculations of the reagents and intermediates of the oxidation reaction were performed at the PM3 level of theory. The deformational distortions of the free macrocycle and during the course of the reaction were estimated. The effect of the structure modification and the degree of deformation of the macrocyclic ligand on the parameters of the process [effective (k eff) and true (k v) rate constants] was found.

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. Bulatov, M.I. and Kalinkin, I.P., Prakticheskoe rukovodstvo po fotokolorimetricheskim i spektrofotometricheskim metodam analiza (Practical Guide of Photocolorimetric and Spectrophotometric Methods of Analysis), Leningrad: Khimiya, 1968.

    Google Scholar 

  2. Stewart, J.J P., J. Comput. Chem., 1989, vol. 10, no. 2, p. 209.

    Article  CAS  Google Scholar 

  3. Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10, no. 2, p. 221.

    Article  CAS  Google Scholar 

  4. Stewart, J.J.P., J. Computer-Aided Molecular Design, 1990, vol. 4, p. 1.

    Article  Google Scholar 

  5. Fletcher, R., Methods of Optimization, New York: Wiley, 1980, p. 45.

    Google Scholar 

  6. Buchler, J.W., Lay, K.L., and Caste, L., Inorg. Chem., 1982, vol. 21, no. 2, p. 842.

    Article  CAS  Google Scholar 

  7. Juan, L.-Ch. and Bruic,e T.C., J. Am. Chem. Soc., 1985, vol. 107, no. 2, p. 512.

    Article  Google Scholar 

  8. Dirk, M. and Hambright, P., J. Chem. Soc. Faraday Trans., 1992, vol. 88, no. 14, p. 2013.

    Article  Google Scholar 

  9. Berezin, B.D. and Sennikova, G. V., Kinetika i Kataliz., 1968, vol. 9, no. 3, p. 528.

    CAS  Google Scholar 

  10. Liston, D.J. and West, B.O., Inorg. Chem., 1985, vol. 24, no. 10, p. 1568.

    Article  CAS  Google Scholar 

  11. Kalish, H., Camp, J.E., Stępień, M., Latos-Grażyński, L., and Balch, A.L., J. Am. Chem. Soc., 2001, vol. 123, no. 47, p. 11719.

    Article  CAS  Google Scholar 

  12. Simonova, O.R., Zaitseva, S.V., Zdanovich, S.A., and Koifman, O.I., Abstract of Papers, V Intern. Conf. on Porphyrins and Phthalocyanins, Moscow, 2008, p. 424.

  13. Zaitseva, S.V., Zdanovich, S.A., and Koifman, O.I., Koord. Khim., 2006, vol. 32, no. 7, p. 504.

    Google Scholar 

  14. Bagdasarya, Kh.S., Teoriya radikal’noi polimerizatsii (Theory of Radical Polymerization), Moscow: Nauka, 1966.

    Google Scholar 

  15. Simonova, O.R., Zaitseva, S.V., and Koifman, O.I., Zh. Obshch. Khim., 2008, vol. 78, no. 6, p. 1033.

    Google Scholar 

  16. Zaitseva, S.V., Zdanovich, S.A., and Koifman, O.I., Zh. Obshch. Khim., 2005, vol. 75, no. 5, p. 847.

    Google Scholar 

  17. Treibs, A. and Haberle, N., Liebigs Ann. Chem. B, 1968, vol. 718, p. 183.

    Article  CAS  Google Scholar 

  18. Mamardashvili, N.Zh., Semeikin, A.S., and Golubchikov, O.A., Zh. Org. Khim., 1993, vol. 29, no. 6, p. 1213.

    CAS  Google Scholar 

  19. Obshchaya organicheskaya khimiya (General Organic Chemistry), Barton, D. and Ollis, W.D., Eds., vol. 2, Moscow: Khimiya, 1982, p. 459.

    Google Scholar 

  20. Eksperimental’nye metody khimicheskoi kinetiki (Experimental Methods of Chemical Kinetic), Emanuel, N.M. and Sergeev, G.B., Eds., Moscow: Vysshaya Shkola, 1980.

    Google Scholar 

  21. Bersuker, I.B., Elektronnoe stroenie i svoistva koordinatsionnykh soedinenii (Electronic Structure and Properties of Coordination Compounds), Leningrad: Khimiya, 1986.

    Google Scholar 

  22. Schidt, MW., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunaga, N., Nguyen, K.A., Su, S., Windus, T.L., Dupuis, M., and Montgomeri, J.A., J. Comput. Chem., 1993, vol. 14, no. 11, p. 1347.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

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

    O. R. Simonova & S. V. Zaitseva

Authors
  1. O. R. Simonova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. V. Zaitseva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. R. Simonova.

Additional information

Original Russian Text © O.R. Simonova, S.V. Zaitseva, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 7, pp. 1180–1186.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Simonova, O.R., Zaitseva, S.V. Effect of imidazole on the structure and properties of Zn-5,15-di(o-methoxyphenyl)-2,8,12,18-tetramethyl-3,7,13,17-tetrabutylporphyrin in reaction with organic peroxides. Russ J Gen Chem 79, 1537–1543 (2009). https://doi.org/10.1134/S1070363209070238

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363209070238

Keywords

Search

Navigation