cis_effect_angew_revise_final.doc (2.12 MB)
Download fileA strong cis-effect in an imidazole-imidazolium-substituted alkene
journal contribution
posted on 21.04.2021, 06:27 authored by Dayne C Georgiou, Mohammad A Haghighatbin, Conor HoganConor Hogan, MS Scholz, JN Bull, EJ Bieske, David WilsonDavid Wilson, Jason DuttonJason DuttonWe 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.