Reaction of 2,4-dinitrochlorobenzene with aromatic amines in toluene: Effect of nucleophile structure

The kinetics of the reaction of 2,4-dinitrochlorobenzene (DNClB) with aniline and substituted anilines such as p-anisidine, p-toluidine and N-methylaniline have been studied in toluene. Except for N-methylaniline the reactions have shown a third order in amine rate dependence which is consistent wit...

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Autores principales: Alvaro, C.E.S., Savini, M.C., Nicotra, V., Yankelevich, J.S., Nudelman, N.S.
Formato: Artículo publishedVersion
Lenguaje:Inglés
Publicado: 2000
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Acceso en línea:http://hdl.handle.net/20.500.12110/paper_14203049_v5_n3_p401_Alvaro
https://repositoriouba.sisbi.uba.ar/gsdl/cgi-bin/library.cgi?a=d&c=artiaex&d=paper_14203049_v5_n3_p401_Alvaro_oai
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Sumario:The kinetics of the reaction of 2,4-dinitrochlorobenzene (DNClB) with aniline and substituted anilines such as p-anisidine, p-toluidine and N-methylaniline have been studied in toluene. Except for N-methylaniline the reactions have shown a third order in amine rate dependence which is consistent with aggregates of the amine acting as the nucleophile. On the other hand, the reaction of DNClB with N-methylaniline under the same conditions shows a linear dependence of the second order rate coefficient, kA, vs [amine], which is consistent with the previous mechanism.