The inverted cucurbit[n]uril family.
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.
Isaacs
Lyle
L
Department of Chemistry and Biochemistry, University of Maryland, College Park, Maryland 20742, USA. LIsaacs@umd.edu
Park
Sang-Kyu
SK
Liu
Simin
S
Ko
Young Ho
YH
Selvapalam
Narayanan
N
Kim
Youngkook
Y
Kim
Hyunuk
H
Zavalij
Peter Y
PY
Kim
Ghyung-Hwa
GH
Lee
Heung-Soo
HS
Kim
Kimoon
K
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
D001952:Bridged-Ring Compounds; D007093:Imidazoles; C456276:cucurbit(7)uril; D047028:Macrocyclic Compounds; D000099246:Cucurbit(n)urils; C454805:cucurbit(6)uril