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

Dayne C GeorgiouMohammad A HaghighatbinConor F HoganMichael S ScholzJames N BullEvan J BieskeDavid J D WilsonJason L Dutton
Published in: Angewandte Chemie (International ed. in English) (2017)
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.
Keyphrases
  • ionic liquid
  • mass spectrometry
  • single molecule
  • high resolution
  • solid state
  • liquid chromatography
  • molecular docking
  • density functional theory
  • molecular dynamics simulations
  • gas chromatography
  • energy transfer