Intramolecular catalysis. Part 2. Mechanism of hydrolysis of alkyl 8-hydroxy-1-naphthoates
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 13,p. 1799-1804
- https://doi.org/10.1039/p29770001799
Abstract
The hydrolysis of alkyl 8-hydroxy-1 -naphthoates in alkaline 30%(v/v) dioxan–water has been investigated. The pH′-rate profiles, activation parameters, comparison with the rates of hydrolysis of model compounds and 8-hydroxy1 -naphthoic acid lactone, and kinetic solvent isotope and other effects indicate a mechanism involving intramolecular catalysis, either by general base or by general acid specific base. The significance of the results is discussed in relation to the factors governing such mechanistic pathways.Keywords
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