Steric, hydrogen-bonding and structural heterogeneity effects on the nucleophilic substitution of N-(p-fluorophenyldiphenylmethyl)-4-picolinium chloride in ionic liquids

CC Weber, AF Masters, T Maschmeyer

Index: Weber, Cameron C.; Masters, Anthony F.; Maschmeyer, Thomas Organic and Biomolecular Chemistry, 2013 , vol. 11, # 15 p. 2534 - 2542

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Citation Number: 12

Abstract

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 ...