Expanding cavitand chemistry: The preparation and characterization of [n]cavitands with n ≥ 4

Christoph Naumann, Esteban Román, Carlos Peinador, Tong Ren, Brian O. Patrick, Angel E. Kaifer, John C. Sherman

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

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-O-Ar 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.

Original languageEnglish (US)
Pages (from-to)1637-1645
Number of pages9
JournalChemistry - A European Journal
Volume7
Issue number8
DOIs
StatePublished - Apr 17 2001

Keywords

  • Cavitands
  • Chemical exchange
  • Host-guest chemistry
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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