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Quantum-chemical study of the electronic structure and geometry of 1-vinylimidazole derivatives

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

Conclusions

  1. 1.

    The spatial parameters and charge distribution in 2-substituted 1-vinyl- and 1-vinylbenzimidazoles were calculated by the MCSCF method. Good correlation was obtained between the calculated and experimental values of the dipole moments.

  2. 2.

    The character of the electronic effect of the substituents was established. The methyl group causes a positive inductive effect. In the presence of hydroxymethyl and O-vinyl groups, a positive mesomeric effect is added to the inductive effect. Charge redistribution is observed due to a change in the conjugation of the π system of the imidazole ring and vinyl group.

  3. 3.

    In 2-substituted 1-vinylimidazoles, perturbation of the coplanarity of the vinyl group and heterocycle causes a decrease in the difference of the charge on the C atoms of the vinyl group which corresponds to a decrease in the difference of the chemical shifts of these atoms in the13C NMR spectra.

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Literature cited

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Authors and Affiliations

  1. Institute of Organic Chemistry, Siberian Branch, Academy of Sciences of the USSR, Irkutsk

    D. K. Danovich, V. K. Voronov, V. G. Zakzhevskii & L. V. Baikalova

Authors
  1. D. K. Danovich
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  2. V. K. Voronov
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  3. V. G. Zakzhevskii
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  4. L. V. Baikalova
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimlcheskaya, No. 9, pp. 2001–2004, September, 1987.

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Danovich, D.K., Voronov, V.K., Zakzhevskii, V.G. et al. Quantum-chemical study of the electronic structure and geometry of 1-vinylimidazole derivatives. Russ Chem Bull 36, 1855–1857 (1987). https://doi.org/10.1007/BF00958329

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  • DOI: https://doi.org/10.1007/BF00958329

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