Expanding Cavitand Chemistry: The Preparation and Characterization of [n]Cavitands with n≥4

✍ Scribed by Christoph Naumann; Esteban Román; Carlos Peinador; Tong Ren; Brian O. Patrick; Angel E. Kaifer; John C. Sherman

• Book ID: 101370307
• Publisher: John Wiley and Sons
• Year: 2001
• Tongue: English
• Weight: 234 KB
• Volume: 7
• Category: Article
• ISSN: 0947-6539
• DOI: 10.1002/1521-3765(20010417)7:8<1637::aid-chem16370>3.0.co;2-x

✦ Synopsis

The preparation of cavitands composed of 4, 5, 6, and 7 aromatic subunits ([n]cavitands, n=4-7) is described. The simple, two-step synthetic procedure utilized readily available starting materials (2-methylresorcinol and diethoxymethane). The two cavitand products having 4 and 5 aromatic subunits exhibited highly symmetric cone conformations, while the larger cavitands (n = 6 and 7) adopt conformations of lower symmetry. 1H NMR spectroscopic studies of [6]cavitand and [7]cavitand revealed that these hosts undergo exchange between equivalent conformations at room temperature. The departure of these two cavitands from cone conformations is related to steric crowding on their Ar-O-CH2-OAr bridges and is predicted by simple molecular mechanics calculations (MM2 force field). X-ray diffraction studies on single crystals of the [4]cavitand, [5]cavitand, and [6]cavitand hosts afforded additional experimental support for these conclusions.