6533b839fe1ef96bd12a5b5f

RESEARCH PRODUCT

Mononuclear rearrangements of heterocycles in water/β-CD: information on the real site of reaction from structural modifications of substrates and from proton concentration dependence of the reactivity

Paolo Lo MeoDomenico SpinelliRenato NotoStefano MorgantiSusanna Guernelli

subject

cyclodextrinProtonConcentration dependenceStereochemistryChemistryElectrospray ionizationOrganic ChemistryDrug DiscoveryProton NMR124-oxadiazoleReactivity (chemistry)mononuclear rearrangementBiochemistry

description

Abstract The effect of β-cyclodextrin (β-CD) on the reactivity in the base-catalyzed pathway for the rearrangement in water of some ( Z )-hydrazones of 3-benzoyl-1,2,4-oxadiazoles ( 1b – f ) into the relevant triazoles ( 2b – f ) was investigated, finding different behavior as a function of the proton concentration. ESIMS and 1 H NMR data evidence the formation of host – guest complexes. The whole of the experimental and calculated (MM2) data enabled us to draw some intriguing conclusions concerning the influence of the structures of the substrates and the nature of the formed host – guest complexes on the real site of the reaction.

yearjournalcountryeditionlanguage
2007-10-01Tetrahedron
https://doi.org/10.1016/j.tet.2007.07.084