Abstract

AbstractThe nucleophilic addition reactions of both the non‐substituted and p‐substituted benzenesulfinic acids with 2‐chloro‐ and 2‐bromoacrylonitriles have been studied. The structures of the 3‐benzenesulfonyl‐2‐halogenopropanenitriles thus obtained were confirmed by microanalytical and spectral methods. The basic kinetic parameters of the reactions were determined and some local electronic descriptors concerning the reaction centers were calculated. For the interaction with benzenesulfinic acids, 2‐bromoacrylonitrile was found to have higher reactivity as a Michael acceptor than 2‐chloroacrylonitrile. The higher reactivity of 2‐bromoacrylonitrile is associated with the higher electrophilicity of its β‐carbon atom, which was proved by its pronounced acceptor delocalizability and increased reaction rate values with the corresponding benzenesulfinic acids.

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