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A Strong cis-Effect in an Imidazole-Imidazolium-Substituted Alkene.
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.
Afiliación
  • Georgiou DC; Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Victoria, 3086, Australia.
  • Haghighatbin MA; Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Victoria, 3086, Australia.
  • Hogan CF; Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Victoria, 3086, Australia.
  • Scholz MS; School of Chemistry, University of Melbourne, Parkville, Victoria, 3010, Australia.
  • Bull JN; School of Chemistry, University of Melbourne, Parkville, Victoria, 3010, Australia.
  • Bieske EJ; School of Chemistry, University of Melbourne, Parkville, Victoria, 3010, Australia.
  • Wilson DJD; Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Victoria, 3086, Australia.
  • Dutton JL; Department of Chemistry and Physics, La Trobe Institute for Molecular Science, La Trobe University, Melbourne, Victoria, 3086, Australia.
Angew Chem Int Ed Engl ; 56(29): 8473-8480, 2017 07 10.
Article en En | MEDLINE | ID: mdl-28429451
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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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2017 Tipo del documento: Article País de afiliación: Australia
Texto completo
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XML
PubMed Links
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Texto completo: 1 Colección: 01-internacional Banco de datos: MEDLINE Idioma: En Revista: Angew Chem Int Ed Engl Año: 2017 Tipo del documento: Article País de afiliación: Australia