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

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    Author
    Georgiou, DC; Haghighatbin, MA; Hogan, CF; Scholz, MS; Bull, J; Bieske, EJ; Wilson, DJD; Dutton, JL
    Date
    2017-07-10
    Source Title
    Angewandte Chemie International Edition
    Publisher
    John Wiley & Sons Ltd.
    University of Melbourne Author/s
    Bull, James; Scholz, Michael; Bieske, Evan
    Affiliation
    School of Chemistry
    Metadata
    Show full item record
    Document Type
    Journal Article
    Citations
    Georgiou, 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 Status
    Open Access
    URI
    http://hdl.handle.net/11343/292795
    DOI
    10.1002/anie.201702287
    ARC Grant code
    ARC/DP150101427
    ARC/DP160100474
    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.

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