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Chemistry of Heterocyclic Compounds

, Volume 25, Issue 5, pp 522–524 | Cite as

The C-H...O and C-H...N intramolecular hydrogen bonds in betainealdehydes of azoles containing the pyridinium cation

  • N. V. Spitsyn
  • R. O. Kochanyan
Article
  • 31 Downloads

Abstract

The comparison of the values of the chemical shifts of the pyridinium protons in the ylides of Β-dicarbonyl compounds and in betainealdehydes of thiazole and imidazole established the presence of the intramolecular C-H...O and C-H...N hydrogen bond between the α-protons of the pyridinium and the oxygen atoms of the formyl group and the nitrogen of the amide fragment in the anionoid part of the betaine. The conclusion was confirmed by the varying influence of the effects of protonation on the character of the deshielding of the α- and γ-protons.

Keywords

Oxygen Hydrogen Nitrogen Hydrogen Bond Organic Chemistry 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature Cited

  1. 1.
    H. Ratajczak and W. J. Orville-Thomas, Molecular Interactions [Russian translation], Mir, Moscow (1984).Google Scholar
  2. 2.
    L. Leiserowitz, Acta Cryst., 32, 775 (1976).Google Scholar
  3. 3.
    R. E. Marsh, S. Ramacumar, and K. Vencatasan, Acta Cryst., 22, 66 (1976).Google Scholar
  4. 4.
    V. F. Kaminskii, R. P. Shibaeva, and O. Ya. Neiland, Zh. Strukt. Khim., 17, 898 (1976).Google Scholar
  5. 5.
    O. Ya. Neiland, R. B. Kampare, D. É. Prikule, and É. É. Liepin'sh, Khim. Geterotsikl. Soedin., No. 3, 379 (1979).Google Scholar
  6. 6.
    I. P. Gragerov, V. K. Pogorelyi, and I. F. Franchuk, The Hydrogen Bond and Rapid Proton Exchange [in Russian], Nauk. Dumka, Kiev (1978).Google Scholar
  7. 7.
    J. W. Emsley, J. Feeny, and L. Sutcliffe, High Resolution NMR Spectroscopy [Russian translation], Vol. 1, Mir, Moscow (1968).Google Scholar
  8. 8.
    R. O. Kochkanyan, A. N. Zaritovskii, G. I. Belova, and S. N. Baranov, Khim. Geterotsikl. Soedin., No. 2, 278 (1975).Google Scholar
  9. 9.
    G. C. Pimentel and A. L. McClellan, The Hydrogen Bond [Russian translation], Mir, Moscow (1964), p. 462.Google Scholar

Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • N. V. Spitsyn
    • 1
  • R. O. Kochanyan
    • 1
  1. 1.Institute of Physico-organic Chemistry and Carbon ChemistryAcademy of Sciences of the Ukrainian SSRDonetsk

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