Octaamidocavitand 2 having potential 8-way hydrogen bonding acceptors as well as donors was obtained by shell-closing reaction between tetrakis(chlorocarbonyl)cavitand 1c and tetraanilinocavitand 1e. Molecular mechanics calculation shows octaamidocavitand 2 has a cavity complimentary to 1,4-disubstituted benzenes such as p-xylene or 1,4-dichlorobenzene. The structural characterizations as well as the molecular recognition phenomena of octaamidocavitand 2 using 1H NMR spectroscopy, mass spectroscopy, and computational analysis will be presented.

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