6533b85bfe1ef96bd12bacba
RESEARCH PRODUCT
Host−Guest Interactions between β-Cyclodextrin and the (Z)-Phenylhydrazone of 3-Benzoyl-5-phenyl-1,2,4-oxadiazole: The First Kinetic Study of a Ring−Ring Interconversion in a “Confined Environment”
Maria Francesca LaganàRenato NotoDomenico SpinelliPaolo Lo MeoSusanna GuernelliSerena Rielasubject
Spectrophotometry InfraredStereochemistryOxadiazoleHydrazoneBeta-CyclodextrinsStereoisomerismOxadiazoleRing (chemistry)Medicinal chemistryInclusion compoundchemistry.chemical_compoundCyclodextrin host-guest interactionsCyclodextrinMoleculeSolutionKineticchemistry.chemical_classificationCyclodextrinsOxadiazolesMolecular StructureCyclodextrinbeta-CyclodextrinsOrganic ChemistryHydrazonesWaterStereoisomerismSettore CHIM/06 - Chimica OrganicaHydrazoneSolutionsKineticsModels ChemicalchemistryCyclizationdescription
The effect of beta-cyclodextrin (beta-CD) on the mononuclear heterocyclic rearrangement of the (Z)-phenylhydrazone of 3-benzoyl-5-phenyl-1,2,4-oxadiazole (1) in aqueous borate buffer at pH = 9.6 has been analyzed at temperatures ranging from 293.15 to 313.15 K. The trend of the absorption spectra of 1 as a function of time has been accounted for with the formation of two different 1:1 complexes between beta-CD and 1, the first, "unreactive" complex being formed faster than the "reactive" one. The occurrence of negative activation enthalpy values for the studied interconversion evidences the kinetic relevance of inclusion processes. Computational models elaborated using the MM2 molecular mechanics force field give an idea of the relative importance of the different complexes, additionally helping us to formulate a suitable reaction scheme.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2002-01-01 |