Effect of beta-cyclodextrin on the hydrolysis of trifluoroacetate esters.
The hydrolysis of p-F, p-Cl, and m-Cl phenyl trifluoracetates was studied in the presence of beta-cyclodextrin (beta-CD). The reactions are inhibited by beta-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 beta-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.
Fernández
M A
MA
Departament de Química, Facultat de Ciències, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain.
de Rossi
R H
RH
Cervelló
E
E
Jaime
C
C