Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 6, Issue 10, Pages 1796-1801Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/b801650j
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The host - guest stability constants for the inclusion of a series of small neutral polar organic guests in cucurbit[7]uril (CB[7]) have been determined in aqueous solution by H-1 NMR titrations. The dependence of the stability constant on the nature of the guests indicates that hydrophobic and dipole - quadrupole interactions are responsible for the binding. The complexation-induced chemical shift changes in the guest proton resonances, coupled with energy-minimization calculations, suggest that the guests are located such that their dipole moment is aligned perpendicular with the quadrupole moment of the CB[7] host. The stability constants for acetone and acetophenone decrease in the presence of Na+ or K+ cations as a result of cation capping of the CB[7] portals.
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