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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
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.
| 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 (former - to 2024) |
| UEA Research Groups: | Faculty of Science > Research Groups > Chemistry of Light and Energy Faculty of Science > Research Groups > Centre for Photonics and Quantum Science |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 28 Feb 2019 16:30 |
| Last Modified: | 25 Sep 2024 13:54 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/70062 |
| DOI: | 10.1002/anie.201702287 |
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