Side chain influencing the interaction between β-cyclodextrin and vanillin

The reason for low encapsulation efficiency of vanillin compared to p -hydroxybenzaldehyde within β -cyclodextrin was investigated. Fourier transform infrared spectra proved intermolecular interaction between guest and β -cyclodextrin. UV–visible studies indicated that vanillin and p -hydroxybenzaldehyde form 1:1 inclusion complexes with β -cyclodextrin. Nuclear magnetic resonance and quantum computational methods gave the most favourable orientation in which the guest molecule (vanillin or p -hydroxybenzaldehyde) is totally sequestered in the hydrophobic cavity of the cyclodextrin with the phenolic end located near the primary hydroxyls of the β -cyclodextrin and the aldehyde group near the secondary hydroxyls with hydrogen bonding formation. Encapsulation efficiency of the β -cyclodextrin inclusion with vanillin is about 29% lower than that with p -hydroxybenzaldehyde. This result could be attributable to the effect that the side chain methoxy group weakened the guest/host non-covalent intermolecular interaction, specifically, hydrogen bond interaction. Copyright © 2012 John Wiley & Sons, Ltd.