Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 15, Pages 4273-4283Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201303520
Keywords
dications; electrospray ionization mass spectrometry; ionic liquids; quantum-chemical calculations; X-ray spectroscopy
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Funding
- EPFL
- Swiss National Science Foundation
- NSERC
- National Natural Science Foundation of China [21171093]
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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.
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