Jump to main content
Jump to site search

Issue 18, 2018
Previous Article Next Article

The effect of varying the anion of an ionic liquid on the solvent effects on a nucleophilic aromatic substitution reaction

Author affiliations

Abstract

A variety of ionic liquids, each containing the same cation but a different anion, were examined as solvents for a nucleophilic aromatic substitution reaction. Varying the proportion of ionic liquid was found to increase the rate constant as the mole fraction of ionic liquid increased demonstrating that the reaction outcome could be controlled through varying the ionic liquid. The solvent effects were correlated with the hydrogen bond accepting ability (β) of the ionic liquid anion allowing for qualitative prediction of the effect of changing this component of the solute. To determine the microscopic origins of the solvent effects, activation parameters were determined through temperature-dependent kinetic analyses and shown to be consistent with previous studies. With the knowledge of the microscopic interactions in solution, an ionic liquid was rationally chosen to maximise rate enhancement demonstrating that an ionic solvent can be selected to control reaction outcome for this reaction type.

Graphical abstract: The effect of varying the anion of an ionic liquid on the solvent effects on a nucleophilic aromatic substitution reaction

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Mar 2018, accepted on 16 Apr 2018 and first published on 16 Apr 2018


Article type: Paper
DOI: 10.1039/C8OB00651B
Citation: Org. Biomol. Chem., 2018,16, 3453-3463
  •   Request permissions

    The effect of varying the anion of an ionic liquid on the solvent effects on a nucleophilic aromatic substitution reaction

    R. R. Hawker, R. S. Haines and J. B. Harper, Org. Biomol. Chem., 2018, 16, 3453
    DOI: 10.1039/C8OB00651B

Search articles by author

Spotlight

Advertisements