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We report the isolation, characterization, and recognition behavior of iCB6 and iCB7, which are diastereomers of CB6 and CB7, respectively, containing a single inverted glycoluril unit. Product resubmission experiments establish that these inverted CBn are intermediates in the mechanism of CBn 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.
Isaacs et al. (Thu,) studied this question.
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