Science and Technology Production
Article
Authorship
Norma Nudelman
;
Silvana Alvaro
;
Mónica Savini
;
NICOTRA, VIVIANA ESTELA
;
Jeanete Yankelevich
Date
1999
Publishing House and Editing Place
Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic
Magazine
Collect.Czech. Chem. Commun.,
vol. 64
(pp. 1583-1593)
Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic
Summary
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SIGEVA
The kinetics of reactions of 1-chloro-2,4-dinitrobenzene with aniline and several substituted aromatic amines, B, in toluene shows a quadratic dependence of the second-order rate constant, kA, on [B], which is preserved even in the presence of increasing amounts of dimethylaniline, while the reaction with N-methylaniline shows a linear dependence of kA vs [B]. All these results are interpreted by the ?dimer nucleophile? mechanism, and confirmed by the effects of a non-nucleophilic hydrogen bond...
The kinetics of reactions of 1-chloro-2,4-dinitrobenzene with aniline and several substituted aromatic amines, B, in toluene shows a quadratic dependence of the second-order rate constant, kA, on [B], which is preserved even in the presence of increasing amounts of dimethylaniline, while the reaction with N-methylaniline shows a linear dependence of kA vs [B]. All these results are interpreted by the ?dimer nucleophile? mechanism, and confirmed by the effects of a non-nucleophilic hydrogen bond acceptor tertiary amine which show the relevance of the structure of the nucleophile and the role of mixed aggregates in defining the mechanisms of aromatic nucleophilic substitutions with amines inaprotic solvents.
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Key Words
AROMATIC AMINESNUCLEOPHYLEKINETIC