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.
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 15 Jun 2001|