Electrostatic and non-covalent interactions in dicationic imidazolium-sulfonium salts with mixed anions

Zhaofu Fei, Dun Ru Zhu, Ning Yan, Rosario Scopelliti, Sergey A. Katsuba, Gabor Laurenczy, Danielle M. Chisholm, J. Scott McIndoe*, Kenneth R. Seddon, Paul J. Dyson

*Corresponding author for this work

Research output: Contribution to journalArticle

15 Citations (Scopus)

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. 

Original languageEnglish
Pages (from-to)4273-4283
Number of pages11
JournalChemistry - A European Journal
Volume20
Issue number15
Early online date03 Mar 2014
DOIs
Publication statusPublished - 07 Apr 2014

Keywords

  • dications
  • electrospray ionization mass spectrometry
  • ionic liquids
  • quantum-chemical calculations
  • X-ray spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)

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