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The kinetics and mechanism of the hydrolysis of esters of cis- and trans-2-hydroxycyclopentanecarboxylic acid and 3-hydroxybutyric acid

Capon, Brian and Page, Michael I. (1971) The kinetics and mechanism of the hydrolysis of esters of cis- and trans-2-hydroxycyclopentanecarboxylic acid and 3-hydroxybutyric acid. Journal of the Chemical Society B, physical organic. pp. 741-744. ISSN 1472-779X

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Abstract

The hydrolysis of ethyl cis-2-hydroxycyclopentanecarboxylate is 1·8 to 11 times faster than that of ethyl cyclopentanecarboxylate in 0·1 M-sodium hydroxide in aqueous dioxan (mole fraction of dioxan 0 to 0·329). This is probably not the result of intramolecular hydrogen bonding since ethyl trans-2-hydroxycyclopentanecarboxylate for which such bonding is not possible reacts as fast or faster than the cis-ester. It is tentatively suggested that the smaller dependence of the rates of hydrolysis of the hydroxy-esters on dioxan concentration compared to the unsubstituted ester is the result of solvent sorting. Similar behaviour is found for the hydrolysis of the 2-naphthyl esters and for the ethyl and 2-naphthyl esters of 3-hydroxybutyric acid.The rates of hydrolysis of the hydroxy-esters are enhanced in borate buffers possibly as a result of borate-ester formation followed by intramolecular nucleophilic catalysis.I.r. spectroscopic studies show that the esters of cis-2-hydroxycyclopentanecarboxylic acid are strongly intramolecularly bonded in carbon tetrachloride solution and that those of 3-hydroxybutyric acid are weakly intramolecularly hydrogen bonded. The esters of trans-2-hydroxycyclopentanecarboxylic acid are not intramolecularly hydrogen bonded.

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 13:42
Last Modified: 12 Nov 2009 13:42
URI: http://eprints.hud.ac.uk/id/eprint/6231

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