Issue 10, 2008

Cucurbit[7]uril host–guest complexes with small polar organic guests in aqueous solution

Abstract

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 1H 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.

Graphical abstract: Cucurbit[7]uril host–guest complexes with small polar organic guests in aqueous solution

Article information

Article type
Paper
Submitted
31 Jan 2008
Accepted
03 Mar 2008
First published
31 Mar 2008

Org. Biomol. Chem., 2008,6, 1796-1801

Cucurbit[7]uril host–guest complexes with small polar organic guests in aqueous solution

I. W. Wyman and D. H. Macartney, Org. Biomol. Chem., 2008, 6, 1796 DOI: 10.1039/B801650J

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