Chemistry of Heterocyclic Compounds

, Volume 16, Issue 12, pp 1261–1267 | Cite as

Quaternary salts of quinolybenzimidazoles

  • I. V. Romanenko
  • A. K. Sheinkman
  • S. N. Baranov
  • V. N. Poltavets
  • N. A. Klyuev


The nitrogen atoms of the benzimidazole ring are alkylated initially in the quaternization of 2-(2-quinolyl)benzimidazole, and the nitrogen atom of the quinoline ring is alkylated only after this. Pyridyl- and quinolylbenzimidazoles and their quaternary salts were synthesized in order to study geometrical isomerism in the dihetaryl series. It was concluded that geometrical isomerism cannot occur in the case of the protonated forms or any other quaternary salts of dihetaryls, since as a result of the mutual electron-acceptor effect of the heteroaromatic cations the carbon-carbon bond between them is converted to a single σ bond, despite the fact that it is a bond between two sp2 carbon atoms.


Nitrogen Organic Chemistry Carbon Atom Nitrogen Atom Quinoline 
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Copyright information

© Plenum Publishing Corporation 1981

Authors and Affiliations

  • I. V. Romanenko
    • 1
  • A. K. Sheinkman
    • 1
  • S. N. Baranov
    • 1
  • V. N. Poltavets
    • 1
  • N. A. Klyuev
    • 1
  1. 1.Institute of Physical Organic Chemistry and Coal ChemistryAcademy of Sciences of the Ukrainian SSRDonetsk

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