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

Georgiou, Dayne C., Haghighatbin, Mohammad A., Hogan, Conor F., Scholz, Michael S., Bull, James N. ORCID: https://orcid.org/0000-0003-0953-1716, Bieske, Evan J., Wilson, David J.D. and Dutton, Jason L. (2017) A Strong cis-Effect in an Imidazole-Imidazolium-Substituted Alkene. Angewandte Chemie - International Edition, 56 (29). pp. 8473-8480. ISSN 1433-7851

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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.

Item Type: Article
Uncontrolled Keywords: cis-effect,conformation analysis,e–z isomerization,nitrogen heterocycles,catalysis,chemistry(all) ,/dk/atira/pure/subjectarea/asjc/1500/1503
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: LivePure Connector
Date Deposited: 28 Feb 2019 16:30
Last Modified: 22 Oct 2022 04:27
URI: https://ueaeprints.uea.ac.uk/id/eprint/70062
DOI: 10.1002/anie.201702287

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