A Strong cis‐Effect in an Imidazole‐Imidazolium‐Substituted Alkene. (21st April 2017)

• Record Type: Journal Article
• Authors: Georgiou, Dayne C.; Haghighatbin, Mohammad A.; Hogan, Conor F.; Scholz, Michael S.; Bull, James N.; Bieske, Evan J.; Wilson, David J. D.; Dutton, Jason L.
• Is Part Of: Angewandte Chemie. Volume 129:Number 29(2017)
• Page Start: 8593
• Page End: 8600
• Publication Date: 2017-04-21
• Subjects: cis-Effekt -- E-Z-Isomerisierung -- Konformationsanalyse -- Stickstoff-Heterocyclen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201702287
• Languages: English
• ISSNs: 0044-8249

Abstract

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.