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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
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

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https://eprints.hud.ac.uk/id/eprint/6196
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https://eprints.hud.ac.uk/id/eprint/6196
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https://eprints.hud.ac.uk/id/eprint/6196
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https://eprints.hud.ac.uk/id/eprint/6196
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https://eprints.hud.ac.uk/id/eprint/6196
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https://eprints.hud.ac.uk/id/eprint/6196
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https://eprints.hud.ac.uk/id/eprint/6196
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https://eprints.hud.ac.uk/id/eprint/6196
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https://eprints.hud.ac.uk/id/eprint/6196
URI:
https://eprints.hud.ac.uk/id/eprint/6196
URI:
https://eprints.hud.ac.uk/id/eprint/6196
Title:
The kinetics and mechanism of the hydrolysis of 2,3-(phenylmethylenedioxy)benzoic acid (OO?-benzylidene-2,3-dihydroxybenzoic acid)
Creators:
Capon, Brian, Page, Michael I. and Sankey, G.H.
Identification Number:
10.1039/P29720000529
Official URL:
http://dx.doi.org/10.1039/P29720000529
Date:
May 1972
Subjects:
Q Science > Q Science (General)
Q Science > QD Chemistry
Schools:
School of Applied Sciences
Library
Item Type:
Article
Depositing User:
Sharon Beastall
Date Deposited:
12 Nov 2009 08:51
Revision:
12
Last Modified:
28 Aug 2021 10:52
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