Abstract
The mechanism of nucleophilic addition of a series of amines to acetonitrile MeC≡N both free and activated in a platinum complex trans-[PtCl2(N ≡CMe)2] was studied in detail by the theoretical methods of quantum chemistry. The influence of the nature of a particular nucleophile on the mechanism, kinetic and thermodynamic characteristics of the processes was elucidated. These reactions proceed according to a concerted highly synchronous mechanism that includes formation of 6-membered transition state consisting of the nitrile, amine, and water molecules. Hydrazine, aliphatic amines, and methylendiamine exhibit the highest reactivity from both kinetic and a thermodynamic viewpoint, while aromatic amines and amidine are the most inert.
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