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Correlating ionic liquid solvent effects with solvent parameters for a reaction that proceeds through a xanthylium intermediate

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Abstract

A unimolecular nucleophilic substitution reaction that proceeds through a xanthylium carbocation was studied in seven ionic liquid solvents. It was found that the general trend in the rate constant with changing proportion of ionic liquid in the reaction mixture was different to that seen for other unimolecular processes, with the rate constant increasing as more ionic liquid was added to the reaction mixture. A significant correlation was found between the natural logarithm of the rate constant and a combination of the Kamlet–Taft solvent parameters. This relationship indicated that the principal interaction involved hydrogen bonding between the ionic liquid and some species along the reaction coordinate. Further, this correlation enables prediction of the effects that other ionic liquids will have on this, and other, reactions that proceed through a similar intermediate.

Graphical abstract: Correlating ionic liquid solvent effects with solvent parameters for a reaction that proceeds through a xanthylium intermediate

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Publication details

The article was received on 16 Aug 2019, accepted on 07 Oct 2019 and first published on 07 Oct 2019


Article type: Paper
DOI: 10.1039/C9OB01807G
Org. Biomol. Chem., 2019, Advance Article

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    Correlating ionic liquid solvent effects with solvent parameters for a reaction that proceeds through a xanthylium intermediate

    A. Gilbert, G. Bucher, R. S. Haines and J. B. Harper, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01807G

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