Synthesis of a New pH-Dependent Ligand: Conformational and Complexation Studies
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.
Keywords: Complexation; Conformational transmitter; Crown-ether; Cyclohexane; pH-switch
Document Type: Research Article
Affiliations: 1: Instituto de Ciencia Molecular, Universidad de Valencia. C/Dr Moliner 50 46100 Burjassot (Valencia) Spain 2: Departamento de Química Orgánica Universidad de Valencia. C/Dr Moliner 50 46100 Burjassot (Valencia) Spain
Publication date: 01 August 2003
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