Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents

The kinetics of the reaction of 2,4-dinitrochlorobenzene with aniline have been studied in toluene and in toluene-methanol binary solvents and compared with the reactions in benzene and chloroform. The reactions in aprotic solvents exhibit a rate dependence that is third-order in amine consistent wi...

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Publicado: 1997
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n10_p2125_Nudelman
http://hdl.handle.net/20.500.12110/paper_03009580_v_n10_p2125_Nudelman
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling paper:paper_03009580_v_n10_p2125_Nudelman2023-06-08T15:27:42Z Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents The kinetics of the reaction of 2,4-dinitrochlorobenzene with aniline have been studied in toluene and in toluene-methanol binary solvents and compared with the reactions in benzene and chloroform. The reactions in aprotic solvents exhibit a rate dependence that is third-order in amine consistent with aggregates of the aniline acting as the nucleophile. Molecular complexes between the aniline and the substrate were also detected spectrophotometrically. Additionally, an inhibitory effect of toluene complexes was observed, which is similar to the previously reported effect of benzene in the reaction of the same substrate with n-butylamine. The reaction in the presence of pyridine shows an amine dependence which indicates formation of 'mixed aggregates' between aniline and pyridine. All the above results, as well as recently reported studies of other reactions different from SNAr, are fully interpreted within the 'dimer nucleophile' mechanism. 1997 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n10_p2125_Nudelman http://hdl.handle.net/20.500.12110/paper_03009580_v_n10_p2125_Nudelman
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description The kinetics of the reaction of 2,4-dinitrochlorobenzene with aniline have been studied in toluene and in toluene-methanol binary solvents and compared with the reactions in benzene and chloroform. The reactions in aprotic solvents exhibit a rate dependence that is third-order in amine consistent with aggregates of the aniline acting as the nucleophile. Molecular complexes between the aniline and the substrate were also detected spectrophotometrically. Additionally, an inhibitory effect of toluene complexes was observed, which is similar to the previously reported effect of benzene in the reaction of the same substrate with n-butylamine. The reaction in the presence of pyridine shows an amine dependence which indicates formation of 'mixed aggregates' between aniline and pyridine. All the above results, as well as recently reported studies of other reactions different from SNAr, are fully interpreted within the 'dimer nucleophile' mechanism.
title Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents
spellingShingle Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents
title_short Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents
title_full Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents
title_fullStr Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents
title_full_unstemmed Aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents
title_sort aggregation effects in the reactions of 2,4-dinitrochlorobenzene with aniline in aprotic solvents
publishDate 1997
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03009580_v_n10_p2125_Nudelman
http://hdl.handle.net/20.500.12110/paper_03009580_v_n10_p2125_Nudelman
_version_ 1768545831484391424

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