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.
We thank the La Trobe Institute for Molecular Sciences, Melbourne University and the Australian Research Council (JLD, DE130100186, FT160100007; EJB DP150101427 and DP160100474) for their generous funding of this project. We acknowledge generous allocations of computing from La Trobe University, Intersect, and NCI.
Angewandte Chemie International Edition
8p. (p. 8473-8480)
John Wiley & Sons Ltd.
The Author reserves all moral rights over the deposited text and must be credited if any re-use occurs. Documents deposited in OPAL are the Open Access versions of outputs published elsewhere. Changes resulting from the publishing process may therefore not be reflected in this document. The final published version may be obtained via the publisher’s DOI. Please note that additional copyright and access restrictions may apply to the published version.