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Electrostatic and Non‐covalent Interactions in Dicationic Imidazolium–Sulfonium Salts with Mixed Anions |
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| Authors: | Dr. Zhaofu Fei Prof. Dun‐Ru Zhu Dr. Ning Yan Dr. Rosario Scopelliti Prof. Sergey A. Katsuba Prof. Gabor Laurenczy Dr. Danielle M. Chisholm Prof. J. Scott McIndoe Prof. Kenneth R. Seddon Prof. Paul J. Dyson |
| Affiliation: | 1. Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015 Lausanne (Switzerland);2. State Key Laboratory of Materials‐Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing Tech University, Nanjing 210009 (P. R. China);3. A. E. Arbuzov Institute of Organic and Physical Chemistry of Kazan, Scientific Centre of the Russian Academy of Sciences, Arbuzov str. 8, 420088 Kazan (Russia);4. Department of Chemistry, University of Victoria, P.O. Box 3065, Victoria, BC, V8W 3V6 (Canada);5. QUILL Centre, The Queen's University of Belfast, Stranmillis Road, Belfast BT9 5AG (UK) |
| Abstract: | A series of thioether‐functionalised imidazolium salts have been prepared and characterized. Subsequent reaction of the thioether‐functionalised imidazolium salts with iodomethane affords imidazolium–sulfonium salts composed of doubly charged cations and two different anions. Imidazolium–sulfonium salts containing a single anion type are obtained either by a solvent extraction method or by anion exchange. The imidazolium–sulfonium salts undergo a methyl‐transfer reaction on exposure to water, giving rise to a new, singly charged imidazolium salt with iodide introduced at the 2‐position of the imidazolium ring. Crystal structures of some of the imidazolium–sulfonium salts were determined by X‐ray crystallography providing the topology of the interactions between the dications and the anions. Electrospray ionization mass spectrometry and quantum‐chemical calculations were used to rationalise the relative strength of these interactions. |
| Keywords: | dications electrospray ionization mass spectrometry ionic liquids quantum‐chemical calculations X‐ray spectroscopy |