Kinetic Studies of Bimolecular Nucleophilic Substitution. VI. Rates of the Menschtkin Reaction of Methyl Iodide with Methylamines and Ammonia in Aqueous Solutions
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The kinetics of the reactions of trimethylamine, dimethylamine, methylamine, and ammonia with methyl iodide in aqueous solutions have been investigated at temperatures ranging from 0 to 40°C. Kinetic analyses of the consecutive methylations of dimethylamine and methylamine have been conducted according to the method of French. In the case of ammonia a standard second-order kinetic treatment can be successfully used because of the relative sluggishness of the first stage as compared with the succeeding stages. The observed rates are in the sequence: Me3N>Me2NH>MeNH2>NH3. The factors which affect this rate sequence are discussed.
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