A strong cis-effect in an imidazole-imidazolium-substituted alkene

Georgiou, Dayne C; Haghighatbin, Mohammad A; Hogan, Conor; Scholz, MS; Bull, JN; Bieske, EJ; Wilson, David; Dutton, Jason

doi:10.26181/607fc5e875feb

A strong cis-effect in an imidazole-imidazolium-substituted alkene

journal contribution

posted on 2021-04-21, 06:27 authored by Dayne C Georgiou, Mohammad A Haghighatbin, Conor HoganConor Hogan, MS Scholz, JN Bull, EJ Bieske, David WilsonDavid Wilson, Jason DuttonJason Dutton

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.

Funding

We thank the La Trobe Institute for Molecular Sciences, Melbourne University and the Australian Research Council (JLD, DE130100186, FT160100007; EJB DP150101427 and DP160100474) for their generous funding of this project. We acknowledge generous allocations of computing from La Trobe University, Intersect, and NCI.

History

Publication Date

2017-01-01

Journal

Angewandte Chemie International Edition

Volume

56

Issue

29

Pagination

8p. (p. 8473-8480)

Publisher

John Wiley & Sons Ltd.

ISSN

1433-7851

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