Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents
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 reactio...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00100765_v64_n1_p1583_Nudelman |
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todo:paper_00100765_v64_n1_p1583_Nudelman2023-10-03T14:08:59Z Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents Nudelman, N.S. Alvaro, C.E.S. Savini, M. Nicotra, V. Yankelevich, J. Amine aggregation states Aprotic solvents Aromatic nucleophilic substitutions Dimer nucleophile mechanism Nucleophile structure Reaction kinetics Reaction mechanism 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00100765_v64_n1_p1583_Nudelman |
| institution |
Universidad de Buenos Aires |
| institution_str |
I-28 |
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R-134 |
| collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Amine aggregation states Aprotic solvents Aromatic nucleophilic substitutions Dimer nucleophile mechanism Nucleophile structure Reaction kinetics Reaction mechanism |
| spellingShingle |
Amine aggregation states Aprotic solvents Aromatic nucleophilic substitutions Dimer nucleophile mechanism Nucleophile structure Reaction kinetics Reaction mechanism Nudelman, N.S. Alvaro, C.E.S. Savini, M. Nicotra, V. Yankelevich, J. Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents |
| topic_facet |
Amine aggregation states Aprotic solvents Aromatic nucleophilic substitutions Dimer nucleophile mechanism Nucleophile structure Reaction kinetics Reaction mechanism |
| description |
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. |
| format |
JOUR |
| author |
Nudelman, N.S. Alvaro, C.E.S. Savini, M. Nicotra, V. Yankelevich, J. |
| author_facet |
Nudelman, N.S. Alvaro, C.E.S. Savini, M. Nicotra, V. Yankelevich, J. |
| author_sort |
Nudelman, N.S. |
| title |
Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents |
| title_short |
Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents |
| title_full |
Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents |
| title_fullStr |
Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents |
| title_full_unstemmed |
Effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents |
| title_sort |
effects of the nucleophile structure on the mechanisms of reaction of 1-chloro-2,4-dinitrobenzene with aromatic amines in aprotic solvents |
| url |
http://hdl.handle.net/20.500.12110/paper_00100765_v64_n1_p1583_Nudelman |
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