NMR spectroscopic characterization of inclusion complexes of hydroxy-substituted naphthalenes with native and modified β-cyclodextrins

Yoshimi Sueishi, Naoya Inazumi, Tadashi Hanaya

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    12 Citations (Scopus)

    Abstract

    The equilibrium constants (K) for the inclusion complexation of three kinds of β-cyclodextrins (β-CDs: native β-CD, heptakis(2,6-di-O- methyl)-β-CD, and 6-O-α-d-glucosyl-β-CD) with OH-substituted naphthalenes (2-naphthol, 2,3-dihydroxynaphthalene, and 2,6- dihydroxynaphthalene) were determined from the induced chemical shifts of NMR measurements for inclusion complexes: K = 188-1,250 mol-1 dm 3. The modified β-CDs form stable 1:1 inclusion complexes with OH-substituted naphthalenes, and the high stability of inclusion complexes of 2,6-dihydroxynaphthalene having a hydrophobic body and hydrophilic ends is shown. In addition, the structures of inclusion complexes were characterized by 2D ROESY NMR measurements. The differences in the structure of the inclusion complexes were observed for three kinds of naphthol guest molecules. Based on the results, the inclusion abilities enhanced by methylation of the OH groups at the CD rim or the side chain of branched β-CD are discussed.

    Original languageEnglish
    Pages (from-to)135-141
    Number of pages7
    JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
    Volume64
    Issue number1-2
    DOIs
    Publication statusPublished - Jun 2009

    Keywords

    • Cyclodextrin
    • Inclusion complex
    • NMR
    • Naphthols
    • ROESY

    ASJC Scopus subject areas

    • Food Science
    • Chemistry(all)
    • Condensed Matter Physics

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