Cucurbit[n]uril : a new molecule in host-guest chemistry

Nial J. Wheate

    Research output: Contribution to journalArticle

    26 Citations (Scopus)

    Abstract

    Cucurbit[n]uril, CB[n], is made from the condensation of glycoluril and formaldehyde in concentrated acid solutions (Fig. 1). It was first made in 1905 as the six-subunit macrocycle CB[6] but its structure was not determined until 1981.[1] Over the last five years the cucurbituril family has been expanded to include cucurbiturils of different sizes (n = 5, 7, 8, 10),[2–5] substituted cucurbiturils, and even inverted cucurbiturils.[6] Cucurbiturils are named for their distinct shape; similar to pumpkins (Cucurbitaceae sp.), and are characterized by their hydrophobic cavity and hydrophilic portals (Fig. 2). Each CB[n] is 9.1 Å long with internal volumes from 82 to more than 500 Å3, and widths between 4.4 and 12.6 Å. Total or partial encapsulation of small guests typically results from ion–dipole and hydrogen bonding interactions between positive charges on the guest and the carbonyl oxygen atoms of the CB[n] portals and/or hydrophobic interactions between the guest and the inner surface of the CB[n] cavity. This article examines some of the important host–guest applications of cucurbit[n]urils in chemistry and biochemistry.
    Original languageEnglish
    JournalAustralian Journal of Chemistry
    Publication statusPublished - 2006

    Keywords

    • carbonyl compounds
    • cucurbituril
    • hydrogen bonding

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