β-cyclodextrin bimodal complexes with n-alkylbenzenes and n-alkylcyclohexanes a molecular mechanics study

The bimodal complexation of phenyl- and cyclohexyl-alkanes in β-cyclodextrin has been studied by means of molecular mechanics calculations using Allinger's MM3 force field. The host shows a computed preference for including the phenyl ring when alkyl chains contain less than five carbon atoms; the computed geometry always locates the phenyl ring at the primary hydroxyl group zone (narrower rim). In contrast, the cyclohexyl ring is computed to be either at the narrower or at the wider part of the host cavity. A good qualitative correlation between computed and experimental dissociation constants for related compounds have been obtained. © 1998 Elsevier Science B.V.