Reactions of carbonyl compounds in basic solutions. Part VII. The mechanism of the alkaline hydrolysis of methyl pseudo-8-acyl-1-naphthoates and pseudo-5-formylphenanthrene-4-carboxylate
- 1 January 1973
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 358-361
- https://doi.org/10.1039/p29730000358
Abstract
Rate coefficients have been measured for the alkaline hydrolysis of a series of methyl pseudo-8-acyl-1-naphthoates and methyl pseudo-5-formylphenanthene-4-carboxylates in 70%(v/v) dioxan–water at several temperatures. The entropies and enthalpies of activation have been evaluated. The results are related to the effects of the substituents and ring size for the pseudo-esters. Solvent isotope effects have been studied for selected pseudo-ester hydrolyses. All the evidence indicates a hydrolysis mechanism with a rate-determining addition of hydroxide anion to the pseudo-ester carbonyl group, followed by rapid collapse of the tetrahedral intermediate to form the carboxylate anion of the corresponding acid as product.Keywords
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