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The relative nucleophilicity of chloride, bromide and iodide anions in [bmim][BF4] ionic liquid has been measured by studying their reaction with methyl p-nitrobenzenesulfonate ([bmim] = 1-butyl-3-methylimidazolium cation). It has been found that iodide is the most nucleophilic halide, and that chloride and bromide have approximately equal nucleophilicities (Cl− is slightly more nucleophilic than Br−) in [bmim][BF4]. Activation energies for the reaction of chloride and bromide with methyl p-nitrobenzenesulfonate have been calculated. The relative nucleophilicity of the halides has been compared with that observed in molecular solvents and in a tetraalkylammonium tetraalkylboride ionic liquid.
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Lancaster et al. (2001) studied this question.
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