A strong cis-effect in an imidazole/imidazolium substituted alkene
AuthorGeorgiou, DC; Haghighatbin, MA; Hogan, CF; Scholz, MS; Bull, J; Bieske, EJ; Wilson, DJD; Dutton, JL
Source TitleAngewandte Chemie International Edition
PublisherJohn Wiley & Sons Ltd.
AffiliationSchool of Chemistry
Document TypeJournal Article
CitationsGeorgiou, D. C., Haghighatbin, M. A., Hogan, C. F., Scholz, M. S., Bull, J., Bieske, E. J., Wilson, D. J. D. & Dutton, J. L. (2017). A strong cis-effect in an imidazole/imidazolium substituted alkene. Angewandte Chemie International Edition, 56 (29), pp.8473-8480. https://doi.org/10.1002/anie.201702287.
Access StatusOpen Access
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.
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