Abstract
Cavitands with self-complementary shapes (3 and 4) were prepared by the covalent attachment of adamantane guest molecules to the upper rim of the host structures. Relatives of the “self-folding” cavitands 2, these new structures possess a seam of intramolecular hydrogen bonds that stabilize the folded conformation. Their self-complementary shapes result in the formation of noncovalent dimers of considerable kinetic and thermodynamic stability (−ΔG295 = 4.5 kcal/mol for 3a and 6.5 kcal/mol for 4a in p-xylene-d10). The dimerization of cavitands 3 and 4 is reversible and subject to control by solvent and temperature. The dimerization process is enthalpically favored and entropy opposed and occurs with significant enthalpy−entropy compensation.
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