Effect of Modifying the Anion of an Ionic Liquid on the Outcome of an SN2 Process
Sinead T. Keaveney A , Dominic V. Francis A , Winnie Cao A B , Ronald S. Haines A and Jason B. Harper A C
+ Author Affiliations
- Author Affiliations
A School of Chemistry, University of New South Wales, Sydney, NSW 2052, Australia.
B Present address: School of Chemical Sciences, The University of Auckland, Private Bag 92019, Auckland 1142, New Zealand.
C Corresponding author. Email: j.harper@unsw.edu.au
Australian Journal of Chemistry 68(1) 31-35 https://doi.org/10.1071/CH14117
Submitted: 6 March 2014 Accepted: 9 April 2014 Published: 26 May 2014
Abstract
The effect of a series of ionic liquids containing different anions (bis(trifluoromethanesulfonyl)imide, dicyanimide, hexafluorophosphate, tetrafluoroborate, and bromide) on the rate constant of a bimolecular substitution process was investigated. A general ionic liquid effect was noted, with increases in the rate constant observed in all ionic liquids used when compared with that in acetonitrile. Temperature-dependent kinetic data allowed calculation of activation parameters in each of the reaction mixtures considered; these parameters showed that the microscopic origins of the rate enhancements observed were not the same for all of the ionic liquids used, demonstrating the importance of the nature of the anion.
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