One-Proton Catalysis in the Intermolecular Imidazole-Catalyzed Hydrolysis of Esters and Amides

Jacob F. Patterson, W Huskey, K. S. Venkatasubban, John L. Hogg

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Abstract

The linear proton inventories observed for the imidazole-catalyzed hydrolysis of both l-acetylimidazole and ethyl trifluorothiolacetate are interpreted in terms of transition-state structures. The observed solvent isotope effects arise from a single transition-state proton (i.e., one-proton catalysis).

Original languageEnglish (US)
Pages (from-to)4935-4938
Number of pages4
JournalJournal of Organic Chemistry
Volume43
Issue number26
DOIs
StatePublished - Jan 1 1978
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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