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

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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.

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Authors and Affiliations

  1. Institute of Physico-organic Chemistry and Carbon Chemistry, Academy of Sciences of the Ukrainian SSR, 340114, Donetsk

    N. V. Spitsyn & R. O. Kochanyan

Authors
  1. N. V. Spitsyn
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  2. R. O. Kochanyan
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 626–628, May, 1989.

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Spitsyn, N.V., Kochanyan, R.O. The C-H...O and C-H...N intramolecular hydrogen bonds in betainealdehydes of azoles containing the pyridinium cation. Chem Heterocycl Compd 25, 522–524 (1989). https://doi.org/10.1007/BF00482497

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  • DOI: https://doi.org/10.1007/BF00482497

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