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The kinetics and mechanism of the hydrolysis of 2,3-(phenylmethylenedioxy)benzoic acid (OO?-benzylidene-2,3-dihydroxybenzoic acid)

Capon, Brian, Page, Michael I. and Sankey, G.H. (1972) The kinetics and mechanism of the hydrolysis of 2,3-(phenylmethylenedioxy)benzoic acid (OO?-benzylidene-2,3-dihydroxybenzoic acid). Journal of the Chemical Society, Perkin Transactions 2 (5). pp. 529-532. ISSN 1472-779X

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Abstract

The hydrolysis of OO-benzylidene-2,3-dihydroxybenzoic acid is considerably faster than that of OO-benzylidene-3,4-dihydroxybenzoic acid and OO-benzylidenecatechol. The pH-rate profile is of the form: kobs=k1/(1 +Ka/10–pH). The high rate is associated with the k1-term which probably arises from intramolecular general-acid catalysis. This kinetic parameters of this reaction are compared with those for the formally analogous inter-molecularly general-acid catalysed hydrolysis of benzylidenecatechol. OO-Benzylidene-2,3-dihydroxybenzoic acid is not intramolecularly hydrogen bonded in dilute solutions in carbon tetrachloride

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Sharon Beastall
Date Deposited: 12 Nov 2009 08:51
Last Modified: 11 Mar 2010 13:57
URI: http://eprints.hud.ac.uk/id/eprint/6196

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