6533b86efe1ef96bd12cb4ce

RESEARCH PRODUCT

Binding equilibria between beta-cyclodextrin and p-nitro-aniline derivatives: the first systematic study in mixed water-methanol solvent systems.

Renato NotoFrancesca D'annaMichelangelo GruttadauriaPaolo Lo MeoSerena Riela

subject

chemistry.chemical_classificationCyclodextrinOrganic ChemistryEnthalpyNitro compoundSettore CHIM/06 - Chimica OrganicaBiochemistryCyclodextrin host-guest complexes polarimetryInclusion compoundSolventchemistry.chemical_compoundAnilinechemistryComputational chemistryDrug DiscoveryNitroMoleculeOrganic chemistry

description

Abstract Complexation equilibria, in mixed water–methanol solvent media, between native β-cyclodextrin and a set of suitably selected p -nitro-aniline derivatives were studied by means of polarimetry. The effects exerted by the organic co-solvent on the conditional inclusion free energies Δ G cond 0 and the differential molar optical rotations Δ Θ were thoroughly analyzed under the perspective of the enthalpy–entropy compensation effect. Experimental data suggest an intimate participation (‘dynamic co-inclusion’) of solvent molecules in the formation and in the conformational dynamics of the host–guest inclusion complex.

10.1016/j.tet.2009.01.008http://hdl.handle.net/10447/36852