Abstract
Six new cavitand bowls are reported (6, 7, 8, 9, 11, and 12), as are three bis-bowl compounds (4, 13, and 14). Eight new complexes (4·guest, 7C·guest, 8C·guest, 9C·guest, 14·guest, 15·guest, 15C·guest, and 16C·guest) that reversibly encapsulate small molecules are reported. Two or more charged-hydrogen bonds (CHBs) or covalent linkages between the bowls are required to form stable complexes. Guest exchange rates vary from milliseconds to days. Thermodynamically, these complexes display an enthalpy−entropy compensation. The relative stability of complex 3·pyrazine versus complex 3·chloroform is 170 000 in nitrobenzene-d5 at 298 K. Apparent stability constants in nitrobenzene-d5 at 298 K yield 1.1 × 109 M-1 for complex 3·pyrazine. The absolute stability constant for complex 4·pyrazine in nitrobenzene-d5 at 333 K is 3.5 × 106 M-1.
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