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Kinetics and mechanism of the bromination of aromatic compounds by N-bromosuccinimide in solution

✍ Scribed by S. Sivakamasundari; R. Ganesan

Publisher
John Wiley and Sons
Year
1980
Tongue
English
Weight
580 KB
Volume
12
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The kinetics of bromination of several aromatic compounds (anilides, anisoles, and phenols) was investigated in 80% aqueous acetic acid (v/v) in the temperature range 20–50Β°C using N‐bromosuccinimide (NBS) as the reagent. The reaction was found to be first order in the aromatic substrate (ArH), and zero order in NBS, the overall order being 1. Stoichiometry of the reaction was 1:1. An increase in solvent polarity increased the reaction rate, and chloride ions were found to be specific catalysts for the reaction. Arrhenius activation energy remained almost constant for all the substrates. A probable mechanism explaining all these observed facts was proposed. The mechanism involved an attack by Br^+^ or more probably by a solvated Br^+^ ion on the aromatic substrate.

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