Skip to main content
Log in

Intramolecular specific C-H... N interactions with participation of the pyridine ring nitrogen atom and amino and imino groups in 2-substituted 1-vinylbenzimidazoles, according to1H and13C NMR data

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

In 1-viny1–2,2′-pyridylbenzimidazole, a double intramolecular specific C-H...N interaction is accomplished between the α-H of the vinyl group with the pyridine ring nitrogen and between the H3′ atom of the pyridine ring and the benzimidazole ring nitrogen. In 1-viny1–2-aminobenzimidazole, there are no intramolecular interactions between the hydrogen atoms of the vinyl group and the nitrogen of the amino group. In 1,3-divinyl-2-iminobenzimidazole, the specific interaction of the imino group nitrogen with the β-cis-hydrogen of the vinyl group is greatly weakened by a degenerate tautomeric equilibrium.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. A. V. Afonin, A. V. Vashchenko, V. K. Voronov, et al., Zh. Org. Khim.,26, 411 (1990).

    Google Scholar 

  2. A. V. Afonin, S. V. Amosova, V. I. Gostevskaya, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1978 (1990).

    Google Scholar 

  3. A. V. Afonin, E. S. Domnina, L. V. Baikalova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2747 (1990).

    Google Scholar 

  4. S. Castellano, H. Gunter, and S. Ebersole, J. Phys. Chem.,69, 4166 (1965).

    Google Scholar 

  5. T. M. Spotswood and C. J. Tanzer, Aust. J. Chem.,20, 1227 (1967).

    Google Scholar 

  6. A. V. Afonin, A. V. Vashchenko, V. K. Voronov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1539 (1990).

    Google Scholar 

  7. A. V. Afonin, A. V. Vashchenko, D. K. Danovich, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1676 (1989).

    Google Scholar 

  8. V. V. Keiko, L. V. Baikalova, E. S. Domnina, et al., Zh. Obshch. Khim.,51, 892 (1981).

    Google Scholar 

  9. A. V. Afonin, B. V. Trzhtsinskaya, N. D. Abramova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1983 (1990).

    Google Scholar 

  10. A. V. Afonin, L. A. Es'kova, V. K. Voronov, et al., Khim. Geterotsikl. Soedin., No. 4, 499 (1989).

    Google Scholar 

  11. M. V. Sigalov, B. A. Trofimov, A. J. Mikhaleva, and G. A. Kalabin, Tetrahedron,37, 3051 (1981).

    Google Scholar 

  12. A. V. Afonin, L. I. Vereshchagin, S. R. Buzilova, et al., Khim. Geterotsikl. Soedin., No. 12, 1662 (1989).

    Google Scholar 

  13. G. V. Shatalov, Monomers and Polymers with Azole and Azine Rings [in Russian], Izd. VGU, Voronezh (1984).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2786–2791, December, 1991.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Afonin, A.V., Baikalova, L.V. & Domnina, E.S. Intramolecular specific C-H... N interactions with participation of the pyridine ring nitrogen atom and amino and imino groups in 2-substituted 1-vinylbenzimidazoles, according to1H and13C NMR data. Russ Chem Bull 40, 2428–2433 (1991). https://doi.org/10.1007/BF00959715

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00959715

Keywords

Navigation