Nucleophilicity in Ionic Liquids. 2.1 Cation Effects on Halide Nucleophilicity in a Series of Bis(trifluoromethylsulfonyl)imide Ionic Liquids

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Abstract
In this work, the nucleophilicities of chloride, bromide, and iodide have been determined in the ionic liquids [bmim][N(Tf)2], [bm2im][N(Tf)2], and [bmpy][N(Tf)2] (where bmim = 1-butyl-3-methylimidazolium, bm2im = 1-butyl-2,3-dimethylimidazolium, bmpy = 1-butyl-1-methylpyrrolidinium, and N(Tf)2 = bis(trifluoromethylsulfonyl)imide). It was found that in the [bmim]+ ionic liquid, chloride was the least nucleophilic halide, but that changing the cation of the ionic liquid affected the relative nucleophilicities of the halides. The activation parameters ΔH⧧, ΔS⧧, and ΔG⧧ have been estimated for the reaction of chloride in each ionic liquid, and compared to a similar reaction in dichloromethane, where these parameters were found for reaction by both the free ion and the ion pair.