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Russian Journal of General Chemistry

, Volume 89, Issue 10, pp 1990–1997 | Cite as

Reactivity of Selected Mono- and Dimethylpyridines under Conditions of Oxidative Ammonolysis

  • P. B. VorobyevEmail author
  • A. P. Serebryanskaya
Article
  • 7 Downloads

Abstract

The reactivity of 3-methyl-, 4-methyl-, 2,3-dimethyl-, and 3,4-dimethylpyridines under the oxidative ammonolysis on vanadium oxide catalysts has been studied. The yield of monocyanopyridines has been related to the simulated values of the deprotonation enthalpy of methyl substituents being converted into the cyano group, both in the gas phase and under conditions simulating chemisorption at the acid center of the catalyst. Differences in the mechanism of conversion of the primary products of oxidative ammonolysis of 2,3- and 3,4-dimethylpyridines (2-cyano-3-methyl- and 4-cyano-3-methylpyridines) at elevated temperature have been revealed.

Keywords

oxidative ammonolysis 3(4)-methylpyridines 2,3(3,4)-dimethylpyridines vanadium oxide catalysts 

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Notes

Conflict of Interests

No conflict of interest was declared by the authors.

References

  1. 1.
    Vorobyev, P.B., Mikhailovskaya, T.P., Serebryanskaya, A.P., and Yugai, O.K., Okislitel’nyi ammonoliz metilaromaticheskikh soedinenii (Oxidative Ammonolysis of Methyl Aromatic Compounds), Almaty: IP Bekitaeva, 2017.Google Scholar
  2. 2.
    Vorobyev, P.B., Gabdrakipov, V.Z., Mikhailovskaya, T.P., and Sembaev, D.K., Russ. J. Gen. Chem., 2001, vol. 71, no. 4, p. 605.  https://doi.org/10.1023/A:1012395504813 CrossRefGoogle Scholar
  3. 3.
    Vorobyev, P.B. and Sembaev, D.K., Russ. J. Gen. Chem., 2005, vol. 75, no. 1, p. 147.  https://doi.org/10.1007/s11176-005-0186-1 CrossRefGoogle Scholar
  4. 4.
    Clarck, T., A Handbook of Computational Chemistry, Wiley, 1985.Google Scholar
  5. 5.
    Koch, W. and Holthausen, M.C., A Chemist’s Guide to Density Functional Theory, Weinheim: Wiley-VCH, 2001, p. 293.CrossRefGoogle Scholar
  6. 6.
    Vorobyev, P. and Serebryanskaya, A.P., Russ. J. Gen. Chem., 2012, vol. 82, no. 12, p. 1987.  https://doi.org/10.1134/S1070363212120146 CrossRefGoogle Scholar
  7. 7.
    Katalizatory organicheskogo sinteza (Organic Synthesis Catalysts), Zakarina, N.A., Ed., Alma-Ata: Gylym, 1992, part 2.Google Scholar
  8. 8.
    Okada, J., Morita, S., and Miwa, Y., Chem. Pharm. Bull., 1974, vol. 22, no. 10, p. 2402.  https://doi.org/10.1248/cpb.22.2402 CrossRefGoogle Scholar
  9. 9.
    Cram, D., Fundamentals of Carbanion Chemistry, New York: Academic Press, 1965.Google Scholar
  10. 10.
    Kabachnik, M.I., Usp. Khim., 1979, vol. 49, no. 9, p. 1523.Google Scholar
  11. 11.
    Reutov, O.A., Beletakaya, I.P., and Butin, K.P., CH-Kisloty (CH-Acids), Moscow: Nauka, 1980.Google Scholar
  12. 12.
    Bates, R. and Ogle, C.A., Carbanion Chemistry, New York: Springer-Verlag, 1983CrossRefGoogle Scholar
  13. 13.
    Margolis, L.Ya., Okislenie uglevodorodov na geterogennykh katalizatorakh (Hydrocarbon Oxidation on Heterogeneous Catalysts), Moscow: Khimiya, 1977.Google Scholar
  14. 14.
    Foresman, J.B. and Frish, A., Exploring Chemistry with Electronic Structures Methods, Pittssburg: Gaussian Inc., 1996, p. 302.Google Scholar
  15. 15.
    Boreskov G.K., Zh. Vsosoyuz. Khim. O-va im. D.I. Mendeleeva, 1977, vol. 22, no. 5, p. 495.Google Scholar
  16. 16.
    Vorobyev P.B., Serebryanskaya, A.P., and Sembaev, D.Kh., Khim. Zh. Kazahstana, 2009, no. 3, p. 182.Google Scholar
  17. 17.
    Spravochnik khimika (Chemist’s Handbook), Nikol’-skii, B.P., Ed., Leningrad: Khimiya, 1964, vol. 2.Google Scholar
  18. 18.
    Vorobyev, P.B., Kurmakyzy, R., Nikitina, A.I., and Sembaev, D.Kh., Khim. Zh. Kazahstana, 2007, no. 1, p. 127.Google Scholar
  19. 19.
    Lyubarskii, A.G., Gorelik, A.G., Sal’nikova, O.N., Glukhova, R.G., Malygin, E.N., and Grabova, M.N., Neftekhim, 1978, vol. 18, no. 3, p. 397.Google Scholar
  20. 20.
    Suvorov, B.V., Promonenkov, V.K., Afanas’eva, T.A., Kan, Tolmacheva, T.P., Serazetdinova, V.A., and Bakirova, S.B., Vestn. AN KazSSR, 1984, no. 3, p. 30.Google Scholar
  21. 21.
    Vorobyev, P.B., Serebryanskaya, A.P., Kurmakyzy, R., and Sembaev, D.Kh., Khim. Zh. Kazahstana, 2007, no. 4, p. 190.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  1. 1.A.B. Bekturov Institute of Chemical SciencesAlmatyKazakhstan

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