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

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Anions
Electrostatics
Negative ions
Salts
Sulfides
Electrospray ionization
X ray crystallography
Iodides
Solvent extraction
Mass spectrometry
Cations
Ion exchange
Crystal structure
Positive ions
Topology
Water

Keywords

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

Cite this

Fei, Z., Zhu, D. R., Yan, N., Scopelliti, R., Katsuba, S. A., Laurenczy, G., ... Dyson, P. J. (2014). Electrostatic and non-covalent interactions in dicationic imidazolium-sulfonium salts with mixed anions. Chemistry - A European Journal, 20(15), 4273-4283. https://doi.org/10.1002/chem.201303520
Fei, Zhaofu ; Zhu, Dun Ru ; Yan, Ning ; Scopelliti, Rosario ; Katsuba, Sergey A. ; Laurenczy, Gabor ; Chisholm, Danielle M. ; McIndoe, J. Scott ; Seddon, Kenneth R. ; Dyson, Paul J. / Electrostatic and non-covalent interactions in dicationic imidazolium-sulfonium salts with mixed anions. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 15. pp. 4273-4283.
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Fei, Z, Zhu, DR, Yan, N, Scopelliti, R, Katsuba, SA, Laurenczy, G, Chisholm, DM, McIndoe, JS, Seddon, KR & Dyson, PJ 2014, 'Electrostatic and non-covalent interactions in dicationic imidazolium-sulfonium salts with mixed anions', Chemistry - A European Journal, vol. 20, no. 15, pp. 4273-4283. https://doi.org/10.1002/chem.201303520

Electrostatic and non-covalent interactions in dicationic imidazolium-sulfonium salts with mixed anions. / Fei, Zhaofu; Zhu, Dun Ru; Yan, Ning; Scopelliti, Rosario; Katsuba, Sergey A.; Laurenczy, Gabor; Chisholm, Danielle M.; McIndoe, J. Scott; Seddon, Kenneth R.; Dyson, Paul J.

In: Chemistry - A European Journal, Vol. 20, No. 15, 07.04.2014, p. 4273-4283.

Research output: Contribution to journalArticle

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AU - Fei, Zhaofu

AU - Zhu, Dun Ru

AU - Yan, Ning

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AU - Katsuba, Sergey A.

AU - Laurenczy, Gabor

AU - Chisholm, Danielle M.

AU - McIndoe, J. Scott

AU - Seddon, Kenneth R.

AU - Dyson, Paul J.

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AB - 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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