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A Strong cis ‐Effect in an Imidazole‐Imidazolium‐Substituted Alkene
Author(s) -
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.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201702287
Subject(s) - imidazole , alkene , chemistry , ring (chemistry) , spectroscopy , mass spectrometry , covalent bond , lone pair , medicinal chemistry , photochemistry , computational chemistry , stereochemistry , organic chemistry , catalysis , molecule , physics , chromatography , quantum mechanics
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.