Issue 35, 2010

Ionicity and proton transfer in protic ionic liquids

Abstract

Proton transfer in protic ionic liquids is poorly understood. Some acid/base proton transfer reactions do not proceed to the extent that is expected from ΔpKaaq data from aqueous solutions, yet some do. In this work we have investigated protic ionic liquids obtained by proton transfer from a common acid, acetic acid, to a range of amine bases of similar pKaaq values. Probe indicator observations, transport property data allowing the construction of Walden plots and computational studies all suggest that there is a clear distinction between the behaviour of simple primary vs. tertiary amines, the proton transfer being more complete in the former case than the latter. The origins of this seem to be related to the hydrogen bonding ability of the ammonium ions in providing a good solvating environment for the ions produced by the proton transfer.

Graphical abstract: Ionicity and proton transfer in protic ionic liquids

Article information

Article type
Paper
Submitted
16 Apr 2010
Accepted
08 Jun 2010
First published
05 Jul 2010

Phys. Chem. Chem. Phys., 2010,12, 10341-10347

Ionicity and proton transfer in protic ionic liquids

J. Stoimenovski, E. I. Izgorodina and D. R. MacFarlane, Phys. Chem. Chem. Phys., 2010, 12, 10341 DOI: 10.1039/C0CP00239A

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