Issue 36, 2014
From the journal:

Organic & Biomolecular Chemistry

Developing principles for predicting ionic liquid effects on reaction outcome. A demonstration using a simple condensation reaction†

Sinead T. Keaveney,a   Karin S. Schaffarczyk McHale,a   Ronald S. Hainesa  and  Jason B. Harper*a  

* 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

Abstract

The effects of a series of ionic liquids, with systematic variations in the cation, on the condensation of an alkyl amine with an aromatic aldehyde were investigated, and the outcomes compared with those predicted based on related reactions. The addition of ionic liquids increased the observed rate constant; the mole fraction dependence of this increase was qualitatively consistent with predictions. Temperature-dependent kinetic analyses were used to demonstrate that the microscopic origins of the effects were as forecast, though the relative weighting of enthalpic and entropic contributions was dependent on the salt used.

Graphical abstract: Developing principles for predicting ionic liquid effects on reaction outcome. A demonstration using a simple condensation reaction

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Article information

DOI
https://doi.org/10.1039/C4OB01070A
Article type
Paper
Submitted
23 May 2014
Accepted
29 Jul 2014
First published
29 Jul 2014

Org. Biomol. Chem., 2014,12, 7092-7099

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Developing principles for predicting ionic liquid effects on reaction outcome. A demonstration using a simple condensation reaction

S. T. Keaveney, K. S. Schaffarczyk McHale, R. S. Haines and J. B. Harper, Org. Biomol. Chem., 2014, 12, 7092 DOI: 10.1039/C4OB01070A

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