Effect of β-cyclodextrin on the hydrolysis of trifluoroacetate esters

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

doi:10.1021/jo001691k

Effect of β-cyclodextrin on the hydrolysis of trifluoroacetate esters

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

Department of Chemistry

Research output: Contribution to journal › Article › Research › peer-review

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 language	English
Pages (from-to)	4399-4404
Journal	Journal of Organic Chemistry
Volume	66
Issue number	12
DOIs	https://doi.org/10.1021/jo001691k
Publication status	Published - 15 Jun 2001

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title = "Effect of β-cyclodextrin on the hydrolysis of trifluoroacetate esters",

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.",

author = "Fern{\`a}ndez, {M. A.} and {De Rossi}, {R. H.} and Enric Cervell{\'o} and Carlos Jaime",

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AU - Fernàndez, M. A.

AU - De Rossi, R. H.

AU - Cervelló, Enric

AU - Jaime, Carlos

PY - 2001/6/15

Y1 - 2001/6/15

N2 - 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.

AB - 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.

U2 - 10.1021/jo001691k

DO - 10.1021/jo001691k

M3 - Article

VL - 66

SP - 4399

EP - 4404

IS - 12

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