Molecular engineering. Part 9: Enhanced binding ability and selectivity of C-2v cavitands

초록

Two new C-2v cavitands with protective side chains were synthesized and their binding properties for small molecules were studied. Cavitand 7 having benzyl side chains binds ethanol most strongly with K-a = 1508 M-1 at 20degreesC in CDCl3, which was driven entropically. Cavitand 8 having coumarinyl side chains showed weaker binding due to its steric hindrance. H-1 NMR spectra show that carceroisomers of ethanol or acetonitrile@cavitand 7 exist in 3:1 ratio at 20degreesC. The binding tendencies of the guest molecules were increased in nonpolar solvent media. (C) 2004 Elsevier Ltd. All rights reserved.

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