Nucleophilic substitutions in mixed solvents. Part VI. The reaction between diethylamine and alkyl halides

Abstract

The rate of reaction between diethylamine and benzyl bromide (RBr) in cyclohexane can be represented approximately by the equation K₂[RBr][Et₂N]+K₃[RBr][Et₂N]². The first term can be neglected in the corresponding reaction with ethyl iodide. Activity coefficient measurements show that the mixture of diethylamine and cyclohexane approximates to a regular solution, so that the above equation suggests that the bimolecular transition state is specifically solvated by an amine molecule. The change in rate with amine concentration is given alternatively by the treatment for associated solutions presented in the preceding Paper.