Reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. Further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution

The reaction of 2,6-dinitroanisole with cyclohexylamine in toluene, octanol and toluene-octanol mixtures has been studied at several amine concentrations. The reactions in toluene and in octanol-toluene mixtures up to 30% octanol show a third-order kinetic dependence on [amine]. Although the reactio...

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Publicado: 1993
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n2_p229_Nudelman
http://hdl.handle.net/20.500.12110/paper_1472779X_v_n2_p229_Nudelman
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_1472779X_v_n2_p229_Nudelman
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spelling paper:paper_1472779X_v_n2_p229_Nudelman2023-06-08T16:17:27Z Reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. Further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution The reaction of 2,6-dinitroanisole with cyclohexylamine in toluene, octanol and toluene-octanol mixtures has been studied at several amine concentrations. The reactions in toluene and in octanol-toluene mixtures up to 30% octanol show a third-order kinetic dependence on [amine]. Although the reaction rates in toluene and octanol are very similar, addition of small amounts of octanol to the toluene solution diminishes the rate of reaction, reaching a minimum value at 30-50% octanol, after which the rate increases almost linearly with the octanol content. These and other results, here described, are satisfactorily explained by the previously proposed 'dimer nucleophile mechanism'. Previously reported similar observations in methanol-benzene mixtures were criticised as being due to the reversibility of the reaction. The present results confirm the previously reported mechanism and the irreversibility of the reaction under the reaction conditions. 1993 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n2_p229_Nudelman http://hdl.handle.net/20.500.12110/paper_1472779X_v_n2_p229_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 reaction of 2,6-dinitroanisole with cyclohexylamine in toluene, octanol and toluene-octanol mixtures has been studied at several amine concentrations. The reactions in toluene and in octanol-toluene mixtures up to 30% octanol show a third-order kinetic dependence on [amine]. Although the reaction rates in toluene and octanol are very similar, addition of small amounts of octanol to the toluene solution diminishes the rate of reaction, reaching a minimum value at 30-50% octanol, after which the rate increases almost linearly with the octanol content. These and other results, here described, are satisfactorily explained by the previously proposed 'dimer nucleophile mechanism'. Previously reported similar observations in methanol-benzene mixtures were criticised as being due to the reversibility of the reaction. The present results confirm the previously reported mechanism and the irreversibility of the reaction under the reaction conditions.
title Reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. Further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution
spellingShingle Reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. Further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution
title_short Reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. Further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution
title_full Reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. Further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution
title_fullStr Reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. Further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution
title_full_unstemmed Reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. Further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution
title_sort reaction of 2,6-dinitroanisole with cyclohexylamine in toluene-octanol binary solvents. further support for the 'dimer nucleophile mechanism' in aromatic nucleophilic substitution
publishDate 1993
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_1472779X_v_n2_p229_Nudelman
http://hdl.handle.net/20.500.12110/paper_1472779X_v_n2_p229_Nudelman
_version_ 1768542192744267776

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