title: The inverted cucurbit[n]uril family.
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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA. LIsaacs@umd.edu
authors.forename: Lyle
authors.initials: L
authors.lastname: Isaacs
authors.forename: Sang-Kyu
authors.initials: SK
authors.lastname: Park
authors.forename: Simin
authors.initials: S
authors.lastname: Liu
authors.forename: Young Ho
authors.initials: YH
authors.lastname: Ko
authors.forename: Narayanan
authors.initials: N
authors.lastname: Selvapalam
authors.forename: Youngkook
authors.initials: Y
authors.lastname: Kim
authors.forename: Hyunuk
authors.initials: H
authors.lastname: Kim
authors.forename: Peter Y
authors.initials: PY
authors.lastname: Zavalij
authors.forename: Ghyung-Hwa
authors.initials: GH
authors.lastname: Kim
authors.forename: Heung-Soo
authors.initials: HS
authors.lastname: Lee
authors.forename: Kimoon
authors.initials: K
authors.lastname: Kim
mesh_terms: D001952:Bridged-Ring Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D007093:Imidazoles / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D013816:Thermodynamics; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils
chemical_list: D001952:Bridged-Ring Compounds; D007093:Imidazoles; C456276:cucurbit(7)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils; C454805:cucurbit(6)uril