NMR STUDY ON THE COMPETITIVE INCLUSION OF SUBSTRATE AND DETERGENT INTO CYCLOHEPTAAMYLOSE CAVITY

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Abstract
The hydrolyses of 4-nitrophenyl and 2,4-dinitrophenyl sulfates have been accelerated in the presence of a functional detergent such as N,N-dimethylhexadecylamine or N,N-dimethyl-N-hexadecyl-N-(4-imidazolium)methylammonium dichloride even at concentrations below cmc, as well as in the presence of cycloheptaamylose (β-CD). Nevertheless, the presence of both β-CD and functional detergent resulted in the diminished rate of hydrolysis of the esters relative to the individual catalysis. Through NMR study on the inclusion behavior of the detergent into the β-CD cavity, the inhibiting effect of β-CD in the hydrolysis of aryl sulfates catalyzed by the functional detergents was ascribed to the competitive inclusion of the substrate and detergent molecules into β-CD.