Skip to main content
SpringerLink
Log in

Structure of quinoxalyformazans in solution

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1(5),3-Diaryl-5(1)-quinoxalylformazans in the solid phase exist in the chelate syn-s-cis-trans conformation, whereas in solutions in CCl4 and CH(D)Cl3 they exist in the form of equilibrium mixtures of chelate and open forms. The percentage and conformation of the open form depend on the character of the substituents in the 1 and 3 positions of the aryl rings. It was established from the 2J13CNH constants that the tautomeric equilibrium is shifted almost completely (no less than 90%) to favor the form with a proton attached to the nitrogen atom bonded to the heteroring.

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

Literature cited

  1. G. V. D. Tiers and S. Plovan, J. Org. Chem., 25, 285 (1960).

    Google Scholar 

  2. P. B. Fischer, B. L. Kaul, and H. Zollinger, Helv. Chim. Acta, 51, 1449 (1968).

    Google Scholar 

  3. E. S. Karavaeva, N. P. Bednyagina, T. A. Sharkova, and I. I. Mudretsova, Khim. Geterotsikl. Soedin., No. 10, 1420 (1975).

    Google Scholar 

  4. I. I. Mudretsova and S. L. Mertslov, Khim. Geterotsikl. Soedin., No. 12, 1666 (1975).

    Google Scholar 

  5. B. I. Buzykin and N. N. Bystrykh. Zh. Org. Khim., 19, 1069 (1983).

    Google Scholar 

  6. G. N. Kipunova, N. N. Gulemina, A. P. Zeif, and N. P. Bednyagina, Khim. Geterotsikl. Soedin., No. 4, 493 (1974).

    Google Scholar 

  7. I. A. Nasyr and V. M. Cherkasov, Khim. Geterotsikl. Soedin., No. 10, 1409 (1976).

    Google Scholar 

  8. G. V. Avramenko, G. A. Maksakova, V. A. Maksakov, and B. I. Stepanov, Zh. Obshch. Khim., 51, 2521 (1981).

    Google Scholar 

  9. J. W. Lewis and C. Sandorfy, Can. J. Chem., 61, 809 (1983).

    Google Scholar 

  10. A. V. El'tsov, A. I. Yalandina, A. I. Ponyaev, G. N. Lipunova, and N. P. Bednyagina, Zh. Obshch. Khim., 53, 2587 (1983).

    Google Scholar 

  11. A. T. Hutton and M. N. H. Irving, Chem. Commun., No. 16, 763 (1980).

    Google Scholar 

  12. A. P. Zeif, G. N. Lipunova, N. P. Bednyagina, L. N. Shchegoleva, and L. I. Chernyavskii, Zh. Org. Khim., 6, 2590 (1970).

    Google Scholar 

  13. L. W. Reeves, F. A. Allan, and K. O. Strömme, Can. J. Chem., 38, 1249 (1960).

    Google Scholar 

  14. N. A. Klyuev, V. G. Zhil'nikov, G. G. Aleksandrov, I. I. Grandberg, and G. N. Lipunova, Zh. Org. Khim., 19, 2615 (1983).

    Google Scholar 

  15. D. A. Ramsay, J. Am. Chem. Soc., 74, 72 (1952).

    Google Scholar 

  16. B. E. Zaitsev, G. V. Sheban, G. V. Shandurenko, G. V. Avramenko, and B. I. Stepanov, Zh. Obshch. Khim., 52, 49 (1982).

    Google Scholar 

  17. M. Kh. Karapet'yants, Introduction to the Theory of Chemical Processes [in Russian], 3rd Edition, Vyssh. Shkola, Moscow (1981), p. 34.

    Google Scholar 

  18. B. I. Buzykin, in: The Chemistry of Hydrazones [in Russian], Nauka, Moscow (1977), p. 196.

    Google Scholar 

  19. Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974), p. 53.

    Google Scholar 

  20. N. M. Sergeev, NMR Spectroscopy [in Russian], Izd. Mosk. Gos. Univ., Moscow (1981), p. 280.

    Google Scholar 

  21. G. Pimentel and O. MacClellan, The Hydrogen Bond, W. H. Freeman, San Francisco (1964).

    Google Scholar 

  22. G. C. Levy and G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, New York (1975).

  23. D. F. Ewing, Org. Magn. Reson., 12, 499 (1979).

    Google Scholar 

  24. S. Balt, J. Meuldijk, and W. E. Renkema, Trans. Met. Chem., 5, 357 (1980).

    Google Scholar 

  25. V. Bekarek, K. Rothschein, P. Vetesnik, and M. Vecera, Tetrahedron Lett., No. 34, 3711 (1968).

    Google Scholar 

  26. V. M. Dziomko, M. N. Stopnikova, L. V. Shmelev, Yu. S. Ryabokobylko, G. M. Adamova, and R. V. Poponova, Khim. Geterotsikl. Soedin, No. 10, 1408 (1980).

    Google Scholar 

  27. H. Mchab, J. Chem. Soc., Perkin Trans. I, No. 2, 357 (1982).

    Google Scholar 

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

    Google Scholar 

  29. H. Pechmann, Ber., 27, 1678 (1894).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. All-Union Scientific-Research Institute of Chemical Reagents and Ultrapure Chemical Substances, 107076, Moscow

    L. V. Shmelev, M. N. Stopnikova, Yu. S. Ryabokobylko, A. V. Kessenikh, G. M. Adamova & V. M. Ostrovskaya

Authors
  1. L. V. Shmelev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. N. Stopnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. S. Ryabokobylko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Kessenikh
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. G. M. Adamova
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. M. Ostrovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 404–412, March, 1985.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shmelev, L.V., Stopnikova, M.N., Ryabokobylko, Y.S. et al. Structure of quinoxalyformazans in solution. Chem Heterocycl Compd 21, 339–347 (1985). https://doi.org/10.1007/BF00506678

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00506678

Keywords

Search

Navigation