Substrate Hydrophobicity and Its Influence on the Transition-State Structure for the Water-Catalyzed Hydrolysis of Acyl Esters

William P. Huskey, Christina T. Warren, John L. Hogg

Research output: Contribution to journalArticle

18 Scopus citations

Abstract

Proton inventories for the “water-catalyzed” hydrolysis of p-nitrophenyl dichloroacetate have been completed in 10-2 N HC1 (DC1) solutions at two different ionic strengths and in a tert-butyl alcohol/water mixture of 0.1 mol fraction of tert-butyl alcohol. The proton inventories exhibit significant downward curvature in all cases and are consistent with greater than three protons contributing to the solvent deuterium isotope effect. The reaction appears to be fourth order or greater with respect to water on the basis of the study in tert-butyl alcohol/water mixtures and the values of the curvature parameter, γ, generated from the proton inventory data. Several possible transition-state structures are considered.

Original languageEnglish (US)
Pages (from-to)59-63
Number of pages5
JournalJournal of Organic Chemistry
Volume46
Issue number1
DOIs
StatePublished - Jan 1981
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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