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Laboratory of Advanced Catalysis for Sustainability, School of Chemistry, The University of Sydney, Sydney 2006, Australia
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; Tel: +61 2 9351 2581
Org. Biomol. Chem., 2013,11, 2534-2542
18 Jan 2013,
21 Feb 2013
First published online
22 Feb 2013
The nucleophilic substitution of N-(p-fluorophenyldiphenylmethyl)-4-picolinium chloride was investigated using water and a range of alcoholic nucleophiles in ionic liquid solvents. The reactivity patterns across the nucleophiles examined could be attributed to steric factors, which mediated the relative nucleophilicities. Reducing the hydrogen-bond acidity of the ionic liquid cation was found to generally increase the rate of reaction, however, the magnitude of this rate effect could be influenced by the steric bulk of the nucleophile and the structural heterogeneity of the ionic liquid. Preferential solvation phenomena in binary mixtures of ionic liquids were examined and suggest that the mechanism behind the hydrogen-bond solvation phenomenon arises from direct cation-mediated, rather than indirect anion-mediated, effects.
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Organic & Biomolecular Chemistry
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