The inverted cucurbit[n]uril family

J Am Chem Soc. 2005 Dec 28;127(51):18000-1. doi: 10.1021/ja056988k.

Abstract

We report the isolation, characterization, and recognition behavior of iCB[6] and iCB[7], which are diastereomers of CB[6] and CB[7], respectively, containing a single inverted glycoluril unit. Product resubmission experiments establish that these inverted CB[n] are intermediates in the mechanism of CB[n] formation. As a consequence of the inverted glycoluril ring, these inverted cucurbiturils possess a permanent dipole moment, are slightly smaller than their diastereomers, show distinctive selectivity in their recognition behavior, and report directly on the contents of their hydrophobic cavity.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged-Ring Compounds / chemistry*
  • Crystallography, X-Ray
  • Imidazoles / chemistry*
  • Kinetics
  • Magnetic Resonance Spectroscopy / methods
  • Models, Molecular
  • Thermodynamics

Substances

  • Bridged-Ring Compounds
  • Imidazoles
  • cucurbit(7)uril
  • cucurbit(6)uril