Chemistry of Heterocyclic Compounds

, Volume 6, Issue 5, pp 624–627 | Cite as

IR spectra and structure of 2- imino-1,3-dimethylbenzimidazolines

  • O. E. Shelepin
  • V. G. Sayapin
  • N. K. Chub
  • A. M. Simonov
Article

Abstract

The fine structure of some N-substituted 2-imino-1,3-dimethyl-benzimidazolines is examined with the aid of IR spectroscopy. It is shown that the introduction of an alkyl or phenyl group into the imino group does not affect the C=N group or the imidazoline ring structure. In salts of 2-imino-1,3-dimethylbenzimidazoline and its N-substituted derivatives, the heterocyclic system has the benzimidazolium structure. The structure of 2-imino-1,3-dimethylbenzimidazolines in which the exocyclic nitrogen atom has electrophilic substituents which are conjugated with the heterocycle is characterized by a considerable contribution from dipolar forms, with the imidazole ring bearing a positive charge.

Keywords

Phenyl Imidazole Nitrogen Atom Fine Structure Positive Charge 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    E. Wilson, G. Decius, and P. Cross, Molecular Vibrations: Theory of Infrared and Raman Vibrational Spectra [Russian translation], IL, 1960.Google Scholar
  2. 2.
    N. D. Vitkevich and A. M. Simonov, ZhOKh, 30, 2868, 1960.Google Scholar
  3. 3.
    N. A. Zakharova, B. A. Porai-Koshits, and L. S. Efros, ZhOKh, 23, 1225, 1953.Google Scholar
  4. 4.
    V. G. Sayapin and A. M. Simonov, KhGS [Chemistry of Heterocyclic Compounds], 1120, 1967.Google Scholar
  5. 5.
    Yu. N. Sheinker, A. M. Simonov, Yu. M. Yutilov, V. N. Sheinker, and E. I. Perel'shtein, ZhOrKh, 2, 917, 1966.Google Scholar
  6. 6.
    K. Nakanishi, Infrared Absorption Spectroscopy, Practical Holden-Day, San Francisco, 1957, p. 45.Google Scholar
  7. 7.
    K. Nakanishi, Infrared Absorption Spectroscopy, Practical Holden-Day, San Francisco, 1957, p. 61.Google Scholar
  8. 8.
    J. E. Brown, J. Am. Chem. Soc., 77, 6341, 1955; N. Jonatan, J. Mol. Spectr., 7, 105, 1961.Google Scholar
  9. 9.
    E. E. Milliaresi and V. A. Izmail'skii, DAN, 146, 1094, 1962; ZhOKh, 35, 776, 1965.Google Scholar
  10. 10.
    E. E. Milliaresi, ZhOKh, 36, 1034, 1966.Google Scholar
  11. 11.
    E. Grison, Acta Cryst., 2, 410, 1949 [cited in 10].Google Scholar
  12. 12.
    A. Kucsman, F. Ruff, J. Kapovits, and J. G. Fischer, Tetrah., 22, 1843, 1966.Google Scholar

Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1973

Authors and Affiliations

  • O. E. Shelepin
    • 1
  • V. G. Sayapin
    • 1
  • N. K. Chub
    • 1
  • A. M. Simonov
    • 1
  1. 1.Rostov-on-Don State UniversityUSSR

Personalised recommendations