Molecular recognition by modified cyclodextrins. Inclusion complexation of β-cyclodextrin 6-O-monobenzoate with acyclic and cyclic hydrocarbons

Abstract

β-Cyclodextrin 6-O-monobenzoate has been synthesized and its complex stability constants (Ks) for acyclic and cyclic hydrocarbons of different size, shape and rigidity evaluated in 1 : 1 methanol–water and/or water by means of differential circular dichroism spectrometry. In the absence of the dipole–dipole and hydrogen-bonding interactions which usually play significant roles in the inclusion complexation of cyclodextrins, the Ks values obtained for the modified cyclodextrin may be more explicitly understood in terms of the size, conformation and rigidity of the guest molecules.