Group Interactions in Polyelectrolytes. VII. Amination Kinetics of Chloromethylated Polystyrene with Butylamine Isomers

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Abstract
The amination of chloromethylated polystyrene (CMPS) and benzyl chloride with butylamine isomers and diethylamine was investigated kinetically in dioxane, methyl ethyl ketone (MEK), and N,N-dimethylformamide (DMF). Although the amination of i- and s-butylamine conformed to the ordinary second-order kinetics in all the solvents, deceleration was observed during the course of the amination of CMPS with n-butylamine in MEK as well as in dioxane, with t-butylamine in DMF, and with diethylamine in both dioxane and DMF. The intrinsic rate constants of the amination of CMPS were generally almost the same as those of benzyl chloride. The magnitudes of the rate constants in each solvent were in this order; n-butyl>i-butyl>s-butyl>t-butyl; it was in the order of DMF>>MEK≈dioxane with all the amines investigated. These results were interpreted in terms of both the structures of the amines and the interaction between the amine and the solvent molecules.
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