Abstract
Kinetics of cleavage of phenylphenyl acetates (PPA) and several para-substituted PPAs in basic aqueous sodium carbonate-bicarbonate buffer containing β-cyclodextrin (CD) have been studied. The reaction exhibits saturation type kinetics and CD accelerates the rate of cleavage by the formation of 1G: 1H inclusion complex. The kinetic results indicate that aryloxy moiety of PPA is included in the hydrophobic cavity of CD. The overall rate constants for the cleavage of the [CD-ester] complex correlate with the Hammett σ-consdtants and Hansch hydrophobicity parameters π. At higher concentrations of CD, there is an additional catalysis due to the formation of weak 1G:2H complex.
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Raj, V., Chandrakala, T. & Rajasekaran, K. Guest-host interactions in the cleavage of phenylphenyl acetates by β-cyclodextrin in alkaline medium. J Chem Sci 120, 325–328 (2008). https://doi.org/10.1007/s12039-008-0055-7
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DOI: https://doi.org/10.1007/s12039-008-0055-7