Kinetic comparison of the relative susceptibility to steric hindrance of an intra- and an inter-molecular cleavage of the ester bond in a series of 2- and 4-carbamoylphenyl esters of 2,4,6-trialkylated benzoic acids
- 1 January 1975
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1062-1068
- https://doi.org/10.1039/p29750001062
Abstract
The rates of intramolecular nucelophilic attack by the amide group and of intermolecular nucleophilic attack by hydroxide ion on the ester carbonyl group of a series of carbamoylphenyl esters of 2,4,6-trialkylated benzoic acids have been determined. Both the intra- and inter-molecular processes showed a closely similar response to progressive increase of steric hindrance about the ester carbonyl group. An excellent correlation of rates along both reaction series with the steric substituent constant (Es) derived by Taft from hydrolyses of esters of aliphatic acids indicated that progressive decoupling of the aromatic ring and the ester group with increasing 2,6-substitution was negligible (except when the substituent is hydrogen).Keywords
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