Molecular recognition study on a supramolecular system (ⅩⅤ)──Molecular recognition of aliphatic alcohols by some phenyl-selenium modified β-cyclodextrins

The spectrophotometric titrations have been performed at 298.15 K in buffered aqueous solution (pH 7.20) to give the stability constants (logK-s) for the supramolecular system formed by mono-6-(phenylseleno)-6-deoxy]-β-cyclodextrin (2), mono-6-(p-tolylseleno)-6-deoxy]-β-cyclodextrin (3), mono-6-(o-tolylseleno)-6-deoxy]-β-cyclodextrin (4), mono-6-(m-tolylseleno)-6-deoxy]-β-cyclodextrin (5) with a series of aliphatic alcohols. The results were compared with the data reported for the parent β-cyclodextrin. The molecular binding ability and selectivity for aliphatic alcohols of modified β-cyclodextrins (2_5) were discussed from the viewpoints of the induced-fit and geometrical complement. The results obtained indicate that the phenylseleno moiety of β-cyclodextrin derivatives (2_5) as a probe for spectrometry can enhance not only the molecular binding ability but also the molecular recognition ability.