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 (K_s) 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 K_s values obtained for the modified cyclodextrin may be more explicitly understood in terms of the size, conformation and rigidity of the guest molecules.