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Mechanism of reaction of azobenzene formation from aniline and nitrosobenzene in basic conditions. General base catalysis by hydroxyide ion
Author(s) -
Dalmagro Jacir,
Yunes Rosendo A.,
Simionatto Edesio Luiz
Publication year - 1994
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610070803
Subject(s) - nitrosobenzene , chemistry , aniline , azobenzene , catalysis , photochemistry , reaction mechanism , base (topology) , concerted reaction , combinatorial chemistry , organic chemistry , polymer chemistry , molecule , mathematical analysis , mathematics
The reaction of nitrosobenzene with aniline, to give azobenzene, in basic conditions was studied. It was shown that the reaction exhibits general base catalysis by different buffers giving a Brønsted coefficient β = 0·318. As in previous studies, a two‐step process with a first step of attack of aniline on nitrosobenzene to give an addition intermediate and a second step of dehydration of this intermediate is proposed to interpret the mechanism of the reaction. The analysis of the Brønsted relationship and of the intermediate of the reaction led to the suggestion that hydoxide ion catalyses the reaction by a mechanism of general base catalysis in the dehydration step.