The interaction between CB[8] and a series of fluorine-substituted di- and tribenzylammonium cations was monitored by 1H  nuclear magnetic resonance spectroscopy. CB[8] encapsulation triggered  significant rotational freezing, and allowed the characterization of  very unusual conformers in its cavity. In the case of  tribenzylammoniums, CB[8] encapsulated regioselectively two of the three  aromatic units. Also, CB[8] displayed remarkable diastereoselectivity  towards ammonium cations bearing a chiral group and three different  benzyl substituents, the nitrogen atom thus becoming the second  stereocenter.

Conformational freezing of fluorine-substituted di- and tribenzylammonium cations in Cucurbit[8]uril: Unusual regio- and stereochemical outcomes

243rd National Meeting (2012)

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