Issue 6, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Solid state nuclear bromination with N-bromosuccinimide. Part 1. Experimental and theoretical studies on some substituted aniline, phenol and nitro aromatic compounds†

Jagarlapudi A. R. P. Sarma*a  and  Akula Nagarajua  

* Corresponding authors

a Molecular Modeling Group, Organic Division-I, Indian Institute of Chemical Technology, Hyderabad, India

Abstract

Solid state bromination of a number of substituted phenol, aniline and nitro aromatic compounds with N-bromosuccinimide yields exclusively the nuclear brominated products. Reactivity in the solid state depends on the reaction time, temperature and nature of the substituent on the substrate. The reaction apparently proceeds by an electrophilic aromatic substitution pathway. Molecular orbital and reaction free energy calculations also support such a view. Thermal analysis and video microscopic observation reveal the nature of the solid state reaction. Crystallinity is required for the reactivity and product selectivity. Product yield decreases with loss of selectivity when the reaction is carried out in a melt or in solution. Unlike the topochemical solid state reactions wherein molecular packing is more important than the intrinsic reactivity, these reactions demonstrate the importance of both these factors.

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Article information

DOI
https://doi.org/10.1039/A905466I
Article type
Paper
Submitted
07 Jul 1999
Accepted
29 Feb 2000
First published
10 May 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 1113-1118

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Solid state nuclear bromination with N-bromosuccinimide. Part 1. Experimental and theoretical studies on some substituted aniline, phenol and nitro aromatic compounds

J. A. R. P. Sarma and A. Nagaraju, J. Chem. Soc., Perkin Trans. 2, 2000, 1113 DOI: 10.1039/A905466I

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