Abstract
The esterolysis of p-nitrophenyl propionate in benzene in the presence of 3–4 × 10–3M amounts of imidazole is very effectively promoted by addition of tetra-alkylammonium carboxylates. The esterolysis rate in the presence of 3–4 × 10–3M amounts of tetra-alkylammonium carboxylates is enhanced by addition of imidazole up to the point where their molar ratio is ca. 1 : 1 and then inhibited by further addition. From the analysis of the kinetic effects observed, including those of water, it is suggested that the main catalytic system is a preformed hydrogen-bonded carboxylate ion–imidazole pair which utilizes the nucleophilic and basic properties of the unsolvated RCO2– anion through the relay action of the imidazole.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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