DEEP-CAVITY RESORCINARENES DIMERIZE THROUGH HYDROGEN-BONDING AND SELF-INCLUSION

The synthesis of new resorcinarene derivatives featuring extended side s and self-complementary hydrogen-bonding sites is described. Dimeriza tion occurs in solvents such as toluene-d(8), and large cavities resul t. The dimerization constant K-D = 1700 +/- 250 M-1 was determined, an d the cavity of the dimer was found to encapsulate two heptyl or octyl chains of the subunits. It is proposed that hydrogen bonding and self -inclusion are responsible for the large and compensating thermodynami c parameters for dimerization: Delta H = -20.9 +/- 1.3 kcal mol(-1) an d Delta S = -58 +/- 5 cal mol(-1) K-1.