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2006.02.27 (16:34:27)


We report the isolation, characterization, and recognition behavior of iCB[6] and iCB[7] which are diastereomers of CB[6] and CB[7], respectively, containing a single inverted glycoluril unit. Product resubmission experiments establish that these inverted CB[n] are intermediates in the mechanism of CB[n] formation.  As a consequence of the inverted glycoluril ring these inverted cucurbiturils possess a permanent dipole moment, are slightly smaller than their diastereomers, show distinctive selectivity in their recognition behavior, and report directly on the contents of their hydrophobic cavity.

J. Am. Chem. Soc., 2005, 127, 18000-18001.