Electrostatic and Non-covalent Interactions in Dicationic Imidazolium-Sulfonium Salts with Mixed Anions

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.


Published in:
Chemistry-A European Journal, 20, 15, 4273-4283
Year:
2014
Publisher:
Weinheim, Wiley-V C H Verlag Gmbh
ISSN:
0947-6539
Keywords:
Laboratories:




 Record created 2014-05-26, last modified 2018-03-17


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