Does the cation really matter? The effect of modifying an ionic liquid cation on an SN2 process

Eden E. L. Tanner; Hon Man Yau; Rebecca R. Hawker; Anna K. Croft; Jason B. Harper

doi:10.1039/C3OB41038B

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Does the cation really matter? The effect of modifying an ionic liquidcation on an S_N2 process†

Eden E. L. Tanner,^a Hon Man Yau,^a Rebecca R. Hawker,^a Anna K. Croft ‡^b and Jason B. Harper*^a

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* Corresponding authors

^a School of Chemistry, University of New South Wales, Sydney, NSW, Australia
E-mail: j.harper@unsw.edu.au
Fax: +61 2 9385 6141
Tel: +61 2 9385 4692

^b Department of Chemical and Environmental Engineering, University of Nottingham, University Park, Nottingham, NG7 2RD, UK

Abstract

The rate of reaction of a Menschutkin process in a range of ionic liquids with different cations was investigated, with temperature-dependent kinetic data giving access to activation parameters for the process in each solvent. These data, along with molecular dynamics simulations, demonstrate the importance of accessibility of the charged centre on the cation and that the key interactions are of a generalised electrostatic nature.

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Article information

DOI: https://doi.org/10.1039/C3OB41038B
Article type: Paper
Submitted: 19 May 2013
Accepted: 02 Aug 2013
First published: 05 Aug 2013

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Org. Biomol. Chem., 2013,11, 6170-6175

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Does the cation really matter? The effect of modifying an ionic liquid cation on an S_N2 process

E. E. L. Tanner, H. M. Yau, R. R. Hawker, A. K. Croft and J. B. Harper, Org. Biomol. Chem., 2013, 11, 6170 DOI: 10.1039/C3OB41038B

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Organic & Biomolecular Chemistry