Cucurbituril
group of chemical compounds
In host–guest chemistry, cucurbiturils are macrocyclic molecules made of glycoluril (=C4H2N4O2=) monomers linked by methylene bridges (−CH2−). The oxygen atoms are located along the edges of the band and are tilted inwards, forming a partly enclosed cavity (cavitand). The name is derived from the resemblance of this molecule with a pumpkin of the family of Cucurbitaceae.
Cucurbiturils are commonly written as cucurbit[n]uril, where n is the number of glycoluril units. Two common abbreviations are CB[n], or simply CBn.
These compounds are particularly interesting to chemists because they are suitable hosts for an array of neutral and cationic species. The binding mode is thought to occur through hydrophobic interactions, and, in the case of cationic guests, through cation-dipole interactions as well. The dimensions of cucurbiturils are generally on the ~10 Å size scale. For instance, the cavity of cucurbit[6]uril has a height ~9.1 Å, an outer diameter ~5.8 Å, and an inner diameter ~3.9 Å.
Cucurbiturils were first synthesized in 1905 by Robert Behrend, by condensing glycoluril with formaldehyde, but their structure was not elucidated until 1981. The field expanded as CB5, CB7, and CB8 were discovered and isolated by Kim Kimoon in the year 2000.
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Datasets, specimens, observations and peer-reviewed methods provide the appropriate test for the technical claims summarized here. The source revision retrieved here is dated Jul 25, 2026. The linked authority identifier is Q59849010. None of the 0 selected statements returned an explicit reference. The first chronological checks are 1905, 1981 and 2000.
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This entry incorporates text from “Cucurbituril” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.