The Finkelstein Reaction in Acetonitrile–Glycol Mixtures. An Approach by a Concurrent Monodentate and Bidentate Solvation Model of the Halide Ion

Abstract

Abstract The rate constant of the reaction of methyl iodide with the bromide ion showed a characteristic dependence on the composition of solvent mixtures. In five solvent mixtures, i.e., acetonitrile–ethylene glycol, –1,2-propanediol, –1,3-butanediol, –1,4-butanediol, and –2,3-butanediol, its dependence was fairly well reproduced by the theoretical equations derived on the basis of the concept of the concurrent monodentate and bidentate solvation of the halide ion by glycol. In contrast, the rate constants in acetonitrile–diethylene glycol and –triethylene glycol mixtures were better reproduced by the modified theoretical equations allowing for a self-association of glycol.