Effect of β-cyclodextrin on the hydrolysis of trifluoroacetate esters

M. A. Fernàndez, R. H. De Rossi, Enric Cervelló, Carlos Jaime

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24 Citations (Scopus)

Abstract

The hydrolysis of p-F, p-Cl, and m-Cl phenyl trifluoracetates was studied in the presence of β-cyclodextrin (β-CD). The reactions are inhibited by β-CD at pH 6 while they are catalyzed in alkaline solution. MM3 calculations reproduce some of the experimental results. The substrates form inclusion complexes with β-CD which are of similar stability as those of the corresponding acetates; however, the association of the transition state is less favorable in these reactions than in those of the acetates, and consequently less stronger catalysis is observed.
Original languageEnglish
Pages (from-to)4399-4404
JournalJournal of Organic Chemistry
Volume66
Issue number12
DOIs
Publication statusPublished - 15 Jun 2001

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