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Configuration of benzoylpyridineoximes studied by 1H and 13C NMR. Effect of protonation of the pyridine nitrogen atom

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A simple and convenient method is proposed for determining the configuration of E,Z-isomers of 2-, 3-, and 4-benzoylpyridines. The difference in chemical shifts (δδ, ppm) in the system CCl4-DMSO-D6 and CCl4-DMSO-CF3COOD for the α-H atoms or the α, Β-C atoms of the pyridine ring can be used to determine the configuration. The shift (δδ) of the α-H signals to weak field is greater for the Z-isomers than for the E-isomers due to protonation of the pyridine nitrogen atom. The reverse dependence is seen in the 13C NMR for the E,Z-isomers. The signals of the α-C atoms shift to stronger field after protonation.

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Authors and Affiliations

  1. Scientific-Research Institute of Pharmacology, USSR Academy of Medical Sciences, 125315, Moscow

    V. P. Lezina, S. G. Rozenberg, O. M. Glozman, L. A. Zhmurenko & V. A. Zagorevskii

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  1. V. P. Lezina
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  2. S. G. Rozenberg
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  3. O. M. Glozman
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  4. L. A. Zhmurenko
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  5. V. A. Zagorevskii
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1073–1077, August, 1990.

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Lezina, V.P., Rozenberg, S.G., Glozman, O.M. et al. Configuration of benzoylpyridineoximes studied by 1H and 13C NMR. Effect of protonation of the pyridine nitrogen atom. Chem Heterocycl Compd 26, 898–902 (1990). https://doi.org/10.1007/BF00480866

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  • DOI: https://doi.org/10.1007/BF00480866

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