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J Am Chem Soc. 2006 Nov 22;128(46):14744-5.

Nor-seco-cucurbit[10]uril exhibits homotropic allosterism.

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  • 1Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.


The condensation of glycoluril and formaldehyde in concentrated HCl at 50 degrees C delivers nor-seco-cucurbit[10]uril (ns-CB [10]). 1H NMR and X-ray crystallographic evidence indicates that the two cavities of ns-CB[10] accommodate guests that are typically bound within CB[6] or CB[7]. Several interesting types of selectivity are possible within these ternary complexes-top/center isomerism, diastereoselective complexation of chiral (but racemic) guest pairs, and guest size controlled homotropic allosterism.

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