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Reactivity of Arenesulfinic Acids as Nucleophiles in the Addition Reaction to 2‐Haloacrylonitriles
Author(s) -
Zvezdova D.,
Stoeva S.,
Aleksiev D.
Publication year - 2007
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200700062
Subject(s) - chemistry , reactivity (psychology) , nucleophile , electrophile , carbon atom , acceptor , medicinal chemistry , reaction rate constant , reaction rate , computational chemistry , photochemistry , organic chemistry , kinetics , catalysis , ring (chemistry) , medicine , physics , alternative medicine , pathology , quantum mechanics , condensed matter physics
The 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.