Search:
Computing and Library Services - delivering an inspiring information environment

The kinetics and mechanism of the hydrolysis of 2,3-(phenylmethylenedioxy)benzene (Oo'-benzylidenecatechol) and benzaldehyde diphenyl acetal

Capon, Brian and Page, Michael I. (1972) The kinetics and mechanism of the hydrolysis of 2,3-(phenylmethylenedioxy)benzene (Oo'-benzylidenecatechol) and benzaldehyde diphenyl acetal. Journal of the Chemical Society, Perkin Transactions 2 (5). pp. 522-529. ISSN 1472-779X

Metadata only available from this repository.

Abstract

General-acid catalysis has been detected in the hydrolysis of OO-benzylidenecatechol with a Brønsted -value of 0·47 for catalysis by carboxylic acids. There is also a relatively fast spontaneous hydrolysis with k(H2O)/(D2O)= 1·61 and S=–21·1 cal deg–1 mol–1 at 75°. The entropy of activation for the hydronium-ion catalysed reaction is –8·78 cal deg–1 mol–1 and the isotope effect k(H3O+)/k(D3O+)= 0·92 at 75°. These reactions are thought to proceed via A-SE2 mechanisms.The hydrolysis of benzaldehyde diphenyl acetal is much faster than that of benzylidenecatechol and in 20%(w/w) dioxan–water mixtures is also general-acid catalysed with approximately 1 and k(H3O+)/k(D3O+)= 0·67 at 15°. An A-SE2 mechanism was also favoured for this reaction

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
Related URLs:
Depositing User: Sharon Beastall
Date Deposited: 12 Nov 2009 08:55
Last Modified: 11 Mar 2010 13:57
URI: http://eprints.hud.ac.uk/id/eprint/6197

Item control for Repository Staff only:

View Item

University of Huddersfield, Queensgate, Huddersfield, HD1 3DH Copyright and Disclaimer All rights reserved ©