Abstract
Abstract Hexakis(3-O-methyl)-α-cyclodextrin (3α) bound to m- and p-nitrophenolate ions more strongly, whereas hexakis(2-O-methyl)-α-cyclodextrin (2α) bound less strongly than native α-cyclodextrin. ROESY spectra showed that the 3-O-methyl groups of 3α interact with the guest protons, whereas 2-O-methyl groups of 2α do not. 3α accelerated and 2α decelerated the cleavage of m-nitrophenyl acetate in an alkaline solution, suggesting that the C(2)–OH of α-cyclodextrin is more catalytic than the C(3)–OH. However, the catalytic effect of 3α was much smaller than that of native α-cyclodextrin. Loss of hydrogen bonding between the C(3)–OH and C(2)–OH by 3-O-permethylation is responsible for the small catalytic effects of 3α. Similar results were obtained for β-cyclodextrin analogs.
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