A Strong cis-Effect in an Imidazole-Imidazolium-Substituted Alkene

Dayne C. Georgiou, Mohammad A. Haghighatbin, Conor F. Hogan, Michael S. Scholz, James N. Bull, Evan J. Bieske, David J.D. Wilson, Jason L. Dutton

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

We report the first example of an alkene with two carbon-bound substituents (imidazole and imidazolium rings) where the Z-isomer has a greater thermodynamic stability than the E-isomer which persists in both the gas phase and in solution. Theoretical calculations, solution fluorescence spectroscopy and gas-phase ion mobility mass spectrometry studies confirm the preference for the Z-isomer, the stability of which is traced to a non-covalent interaction between the imidazole lone pair and the imidazolium ring.

Original languageEnglish
Pages (from-to)8473-8480
Number of pages8
JournalAngewandte Chemie - International Edition
Volume56
Issue number29
Early online date21 Apr 2017
DOIs
Publication statusPublished - 5 Jul 2017

Keywords

  • cis-effect
  • conformation analysis
  • E–Z isomerization
  • nitrogen heterocycles

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