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Issue 6, 2000
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Solid state nuclear bromination with N-bromosuccinimide. Part 2. Experimental and theoretical studies of reactions with some substituted benzaldehydes

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Abstract

N-Bromosuccinimide reacts with aromatic aldehydes in the solid state to yield exclusively nuclear brominated products while a similar reaction in the solution phase produces a number of products under varied conditions. The reactivity and regioselectivity have been studied in terms of the energies of HOMO, HOMO–LUMO difference, reaction free energy, reaction conditions and crystal packing. Single crystal X-ray structural analysis of 3,4-dihydroxybenzaldehyde has been carried out. Crystal packing energies of some of the reactive and unreactive benzaldehydes indicate the importance of molecular bromine diffusion in the solid state.

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Publication details

The article was received on 07 Jul 1999, accepted on 29 Feb 2000 and first published on 09 May 2000


Article type: Paper
DOI: 10.1039/A905468E
J. Chem. Soc., Perkin Trans. 2, 2000, 1119-1123

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    Solid state nuclear bromination with N-bromosuccinimide. Part 2. Experimental and theoretical studies of reactions with some substituted benzaldehydes

    J. A. R. P. Sarma, A. Nagaraju, K. K. Majumdar, P. M. Samuel, I. Das, S. Roy and A. J. McGhie, J. Chem. Soc., Perkin Trans. 2, 2000, 1119
    DOI: 10.1039/A905468E

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