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Oxidation of 3-(3-or 4-pyridyl)-1,5-diphenylformazans in tetrazolium trichlorometallates: Structural and electrochemical investigation

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

On interacting pyridine-containing formazans with cobalt(II) and copper(II) chlorides the richlorometallates of the corresponding cations are isolated, the structures of which were established by X-ray structural analysis. Using data of cyclic voltamperometry a scheme is proposed for the oxidation-reduction process of converting formazans into tetrazolium cations.

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References

  1. J.-M. Lehn, Supramolecular Chemistry: Concepts and Prospects [Russian translation], Izdanie, Novosibirsk (1995).

    Google Scholar 

  2. C. Janiak, J. Chem. Soc., Dalton Trans., 2781 (2003).

  3. V. Yu. Kukushkin and A. J. L. Pombeiro, Chem. Rev., 102, 1771 (2002).

    Article  CAS  Google Scholar 

  4. M. N. Kopylovich, A. J. L. Pombeiro, A. Fischer, L. Kloo, and V. Yu. Kukushkin, Inorg. Chem., 42, 7239 (2003).

    Article  CAS  Google Scholar 

  5. V. D. Vreshch, A. N. Chernega, J. A. K. Howard, J. Sieler, and K. V. Domasevitch. J. Chem. Soc., Dalton Trans., 1707 (2003).

  6. V. Yu. Kukushkin and A. J. L. Pombeiro, Inorg. Chim. Acta, 358, 1 (2005).

    Article  CAS  Google Scholar 

  7. I. Hausser, D. Jerehel, and R. Kuhn, Chem. Ber., 82, 515 (1949).

    CAS  Google Scholar 

  8. B. I. Buzykin, G. N. Lipunova, L. P. Sysoeva, and L. I. Rusinova, Chemistry of Formazans [in Russian], Nauka, Moscow (1992).

    Google Scholar 

  9. L. Hunter and C. Roberts, J. Chem. Soc., 820 (1941).

  10. L. Hunter and C. Roberts, J. Chem. Soc., 823 (1941).

  11. A. Siedle and L. Pignolet, Inorg. Chem., 19, 2052 (1980).

    Article  CAS  Google Scholar 

  12. Kh. M. Severo, B. E. Zaitsev, V. I. Ivlieva, G. V. Avramenko, T. S. Kolodina, and B. I. Stepanov, Zh Neorg. Khim., 29, 2314 (1984).

    CAS  Google Scholar 

  13. A. S. Batsanov, Yu. T. Struchkov, Kh. M. Severo, B. E. Zaitsev, and V. I. Ivlieva, Zh. Neorg. Khim., 32, 93 (1987).

    CAS  Google Scholar 

  14. H. Irving, J. B. Gill, and W. R. Cross, J. Chem. Soc., 2087 (1960).

  15. D. J. Dale, J. Chem. Soc., A, 278 (1967).

  16. I. N. Polyakova, Z. A. Starikova, O. P. Sulim, and G. N. Lipunova, Kristallogr., 37, 653 (1992).

    CAS  Google Scholar 

  17. C. Banciu, Rev. Roum. Chim., 44, 3 (1999).

    CAS  Google Scholar 

  18. K. Ohashi, K. Kurosawa, and K. Yamamoto, Bunseki Kagaku, 32, E361 (1983).

    CAS  Google Scholar 

  19. G. N. Lipunova, E. I. Krylov, N. P. Bednyagina, and V. A. Sharov, Zh. Obshch. Khim., 39, 1293 (1969).

    CAS  Google Scholar 

  20. I. I. Shevelina, L. P. Sidorova, V. N. Podchainova, and N. P. Bednyagina, Zh. Obshch. Khim., 42, 2546 (1972).

    CAS  Google Scholar 

  21. R. I. Ogloblina, N. P. Bednyagina, and A. D. Garnovskii, Zh. Obshch. Khim., 40, 367 (1970).

    CAS  Google Scholar 

  22. N. N. Gumileva, L. F. Lipatova, G. N. Lipunova, and N. P. Bednyagina, Khim. Geterotsikl. Soedin., 774 (1974). [Chem. Heterocycl. Comp., 10, 671 (1974)].

    Google Scholar 

  23. N. N. Gumelina, G. N. Lipunova, N. P. Bednyagina, and S. L. Mertsalov, Zh. Org. Khim., 5, 1108 (1977).

    Google Scholar 

  24. N. P. Bedyagina and G. N. Lipunova, Khim. Geterotsikl. Soedin., 877 (1969). [Chem. Heterocycl. Comp., 5, 652 (1969)].

    Google Scholar 

  25. A. D. Garnovskii, N. P. Bednyagina, L. I. Kuznetsova, V. T. Panyushkin, O. A. Osipov, R. I. Ogloblina, and A. P. Novikova, Zh. Neorg. Khim., 14, 1576 (1969).

    CAS  Google Scholar 

  26. H. J. Cottrell, D. L. Pain, and R. Slack, J. Chem. Soc., 2968 (1954).

  27. E. Suenaga, Yakugaku Zasshi, 79, 803 (1959); Chem. Abs., 21938 (1959).

    CAS  Google Scholar 

  28. W. Ried and H. Gick, Ann. Chimie (Paris), 581, 16 (1951).

    Google Scholar 

  29. J. N. Ashley, B. M. Davis, A. W. Nineham, and R. Slack, J. Chem. Soc., 3881 (1953).

  30. A. Eibner and K. Hofmann, Chem. Ber., 3011 (1904).

  31. W. Ried, Angew. Chem., 64, 391 (1952).

    CAS  Google Scholar 

  32. M. Seyhan, Chem. Ber., 646 (1955).

  33. L. Mester, J. Am. Chem. Soc., 4301 (1955).

  34. S. V. Shinkorenko, G. T. Pilyugin, and G. B. Finkel’, Zh. Obshch. Khim., 42, 2551 (1972).

    CAS  Google Scholar 

  35. M. Seyhan and W. C. Fernelius, J. Am. Chem. Soc., 217 (1957)

  36. E. S. Karavaeva, N. P. Bednyagina, T. A. Sharkova, and I. I. Mudretsova, Khim. Geterotsikl. Soedin., 1420 (1975). [Chem. Heterocycl. Comp., 11, 1208 (1975)].

    Google Scholar 

  37. K. Mukai, M. Matsubara, H. Hisatou, Y. Hosokoshi, K. Inoue, and N. Azuma, J. Phys. Chem.(B), 106, 8632 (2002).

    CAS  Google Scholar 

  38. M. Kishita, Y. Mito, and M. Kubo, Aust. J. Chem., 11, 309 (1958).

    Article  CAS  Google Scholar 

  39. M. I. Ermakova, E. I. Krylov, and I. Ya. Postovskii, Zh. Obshch. Khim., 30, 849 (1960).

    CAS  Google Scholar 

  40. R. Price, J. Chem. Soc. A, 3378 (1971).

  41. M. Predota, V. Petricek, Z. Zak, T. Glowiak, and J. Novotny, Acta Crystallogr,. C47, 738 (1991).

    CAS  Google Scholar 

  42. R. Luboradzki, W. Kozminski, and L. Stefaniak, J. Crystallogr. Spectrosc. Res., 23, 133 (1993).

    Article  CAS  Google Scholar 

  43. R. Luboradzki, J. Lipkowski, W. Kozminski, and L. Stefaniak, J. Chem. Crystallogr., 25, 29 (1995).

    Article  CAS  Google Scholar 

  44. V. M. Divjakovic, V. M. Leovac, B. Ribar, G. Argay, and A. Kalman, Acta Crystallogr. B, 38, 1738 (1982).

    Article  Google Scholar 

  45. G. A. Bogdanovic, V. B. Medakovic, L. S. Vojinovic, V. I. Cesljevic, V. M. Leovac, A. Spasojevic-de Bire, and S. D. Zaric, Polyhedron, 20, 2231 (2001).

    Article  CAS  Google Scholar 

  46. M. Bloy, M. Kretschmann, S. Scholz, M. Teichert, and U. Diefenbach, Z. Anorg. Allg. Chem., 626, 1946 (2000).

    Article  CAS  Google Scholar 

  47. Hao Xu, Jinyu Ji, Zhongzhi Wu, Jianzhong Zou, Zheng Xu, and Xiaozeng You, Polyhedron, 12, 2261 (1993).

    Article  CAS  Google Scholar 

  48. Tian-Tian Pan and Duan-Jun Xu, Acta Crystallogr., E60, m56 (2004).

    Google Scholar 

  49. C. M. Armstrong. P. V. Bernhardt, Piao Chin, and D. R. Richardson, Eur. J. Inorg. Chem., 1145 (2003).

  50. F. E. Hahn, D. Scharn, and T. Lugger, Z. Kristallogr.-New Cryst. Struct., 212, 472 (1997).

    CAS  Google Scholar 

  51. A. Skorska, B. J. Oleksyn, and J. Sliwinski, Enantiomer, 7, 295 (2002).

    Article  CAS  Google Scholar 

  52. P. Pytel, B. J. Oleksyn, and J. Sliwinski, Enantiomer, 6, 201 (2001).

    CAS  Google Scholar 

  53. P. C. Healy, C. Pakawatchai, and A. H. White, Aust. J. Chem., 38, 669 (1985).

    Article  CAS  Google Scholar 

  54. J. M. Savariault, J. Galy, J. M. Gutierrez-Zorilla, and P. Roman, J. Mol. Struct., 176, 313 (1988).

    Article  CAS  Google Scholar 

  55. R. Clerac, F. A. Cotton, S. P. Jeffery, C. A. Murillo, and Xiaoping Wang, Dalton Trans., 3022 (2003).

  56. A. V. Navlyuk, V. N. Davydov, and M. G. Mys’kiv, Koordin. Khim., 27, 917 (2001).

    Google Scholar 

  57. M. Lacan, I. Tabakovic, and Z. Cecovic, Tetrahedron, 30, 2991 (1974).

    Article  Google Scholar 

  58. A. M. Mattson, C. O. Jensen, and R. A. Duther, J. Am. Chem. Soc., 70, 1284 (1948).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Moscow M. V. Lomonosov State University, Moscow, 119992, Russia

    N. A. Frolova, S. Z. Vatsadze, R. D. Rakhimov & N. V. Zyk

  2. Karpov Institute of Physical Chemistry, Moscow, 105064, Russia

    A. I. Stash

Authors
  1. N. A. Frolova
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  2. S. Z. Vatsadze
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  3. A. I. Stash
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  4. R. D. Rakhimov
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  5. N. V. Zyk
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Dedicated to deeply respected Academician M. G. Voronkov in connection with his birthday and as a mark of gratitude for his contribution to heterocyclic chemistry

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1682–1696, November, 2006.

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Frolova, N.A., Vatsadze, S.Z., Stash, A.I. et al. Oxidation of 3-(3-or 4-pyridyl)-1,5-diphenylformazans in tetrazolium trichlorometallates: Structural and electrochemical investigation. Chem Heterocycl Compd 42, 1444–1456 (2006). https://doi.org/10.1007/s10593-006-0261-5

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  • DOI: https://doi.org/10.1007/s10593-006-0261-5

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