6533b857fe1ef96bd12b431f

RESEARCH PRODUCT

Synthesis of a New pH-Dependent Ligand: Conformational and Complexation Studies

Ana M. CosteroJ. Pablo VillarroyaM. Carmen Ramírez De ArellanoSalvador GilPablo Gaviña

subject

chemistry.chemical_classificationCrystallography1h nmr spectroscopychemistry.chemical_compoundchemistryCyclohexaneStereochemistryPh dependentGeneral ChemistryMacrocyclic ligandLigand (biochemistry)Ring (chemistry)Crown ether

description

A new macrocyclic ligand, 3, which exhibits pH-induced conformational changes, has been prepared. This ligand consists of a crown ether derived from a trans-anti-trans 1,2,4,5-tetrasubstituted cyclohexane. Due to the stereochemistry of the substituents on the carbocyclic ring, two different low-energy conformations of the crown ether are possible. Ligand 3 has been studied in solution by 1H NMR spectroscopy at different values of pH and temperature, showing that the conformation of the crown ether, and thus its complexing ability, is strongly pH-dependent. The solid-state structure of the ligand has been determined by X-ray diffraction.

https://doi.org/10.1080/1061027031000116001