Effects of the Nucleophile Structure on the Mechanisms of Reaction of 1-Chloro-2,4-dinitrobenzene with Aromatic Amines in Aprotic Solvents

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Title:Effects of the Nucleophile Structure on the Mechanisms of Reaction of 1-Chloro-2,4-dinitrobenzene with Aromatic Amines in Aprotic Solvents
Creators:
Nudelman, Norma Sbarbati
Alvaro, Cecilia E. Silvana
Savini, Monica
Nicotra, Viviana
Yankelevich, Jeannette
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 10, pp. 1583-1593
Uncontrolled Keywords:Amine aggregation states, Reaction kinetics, Nucleophile structure, Aprotic solvents, Aromatic nucleophilic substitutions, Dimer nucleophile mechanism, Reaction mechanism

Abstract

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, <i>k</i><sub>A</sub>, on [B], which is preserved even in the presence of increasing amounts of dimethylaniline, while the reaction with <i>N</i>-methylaniline shows a linear dependence of <i>k</i><sub>A</sub>&nbsp;<i>vs</i> [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 in aprotic solvents. <p>

Title:Effects of the Nucleophile Structure on the Mechanisms of Reaction of 1-Chloro-2,4-dinitrobenzene with Aromatic Amines in Aprotic Solvents
Creators:
Nudelman, Norma Sbarbati
Alvaro, Cecilia E. Silvana
Savini, Monica
Nicotra, Viviana
Yankelevich, Jeannette
Uncontrolled Keywords:Amine aggregation states, Reaction kinetics, Nucleophile structure, Aprotic solvents, Aromatic nucleophilic substitutions, Dimer nucleophile mechanism, Reaction mechanism
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:64
Number:10
Page Range:pp. 1583-1593
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19991583UNSPECIFIED
ID Code:1580
Item Type:Article
Deposited On:06 Feb 2009 17:10
Last Modified:06 Feb 2009 16:10

Citation

Nudelman, Norma Sbarbati; Alvaro, Cecilia E. Silvana; Savini, Monica; Nicotra, Viviana; Yankelevich, Jeannette (1999) Effects of the Nucleophile Structure on the Mechanisms of Reaction of 1-Chloro-2,4-dinitrobenzene with Aromatic Amines in Aprotic Solvents. Collection of Czechoslovak Chemical Communications, 64 (10). pp. 1583-1593. ISSN 0010-0765

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