Effect of β-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.