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

Dayne C Georgiou; Mohammad A Haghighatbin; Conor F Hogan; Michael S Scholz; James Bull; Evan J Bieske; David JD Wilson; Jason L Dutton

Journal article

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

Dayne C Georgiou, Mohammad A Haghighatbin, Conor F Hogan, Michael S Scholz, James Bull, Evan J Bieske, David JD Wilson, Jason L Dutton

Angewandte Chemie International Edition | John Wiley & Sons Ltd. | Published : 2017

DOI: 10.1002/anie.201702287

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.

University of Melbourne Researchers

Evan Bieske Author Chemistry

Related Projects (2)

Ions in the Fire: Laser Spectroscopy of Cryogenically Cooled Molecular Ions

This project will combine sophisticated laser and mass spectrometric techniques to probe the structure and function of cryogenically cooled ..

Shape-Shifting Molecules: Photoisomerization Action Spectroscopy

This project aims to examine molecules that change shape in response to light in order to gain insight into the biological processes they co..

Grants

Awarded by Australian Research Council

Funding Acknowledgements

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.