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Investigation of structure of immonium salts by means of13C and1H NMR spectrometry

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    13C and1H NMR has been used in investigating the structure of azacations. It has been found that the cations exist in the form of Immonium salts, and the contribution of the limiting structure, which is an aminocarbonium ion, is small. The cations of the protonated imines have mainly the trans configuration.

  2. 2.

    The presence of aryl substituents leads to partial delocalization of plus charge from the N=C bond onto the aromatic rings bonded to the N atom and/or to the methylene C atom.

  3. 3.

    A determination has been made of β-Isotope effects on\(\delta ^{13} C\mathop N\limits^ + = C\) and\(---C---\mathop N\limits^ + = \) carbons: the deuterium isotope shift of carbon resonance corresponds to an increase in screening of the carbon nuclei.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    V. S. Bogdanov, S. S. Krylov, S. N. Shvedova & V. A. Tartakoyskii

Authors
  1. V. S. Bogdanov
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  2. S. S. Krylov
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  3. S. N. Shvedova
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  4. V. A. Tartakoyskii
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1974–1979, September, 1987.

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Bogdanov, V.S., Krylov, S.S., Shvedova, S.N. et al. Investigation of structure of immonium salts by means of13C and1H NMR spectrometry. Russ Chem Bull 36, 1829–1834 (1987). https://doi.org/10.1007/BF00958323

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  • DOI: https://doi.org/10.1007/BF00958323

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