Solvents effects on aromatic nucleophilic substitutions. Part 5. Kinetics of the reactions of 1-fluoro-2,4-dinitrobenzene with piperidine in aprotic solvents

1987 ◽  
pp. 951 ◽  
Author(s):  
Norma S. Nudelman ◽  
Pedro M. E. Mancini ◽  
Rub�n D. Martinez ◽  
Leonor R. Vottero
Keyword(s):  
Aprotic Solvents ◽  
Nucleophilic Substitutions ◽  
Kinetics Of

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

1999 ◽  
Vol 64 (10) ◽  
pp. 1583-1593 ◽  
Author(s):  
Norma Sbarbati Nudelman ◽  
Cecilia E. Silvana Alvaro ◽  
Monica Savini ◽  
Viviana Nicotra ◽  
Jeannette Yankelevich
Keyword(s):  
Hydrogen Bond ◽  
Tertiary Amine ◽  
Aromatic Amines ◽  
Order Rate Constant ◽  
Aprotic Solvents ◽  
Nucleophilic Substitutions ◽  
Hydrogen Bond Acceptor ◽  
Mixed Aggregates ◽  
Kinetics Of

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 in aprotic solvents.

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