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-ener...

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Published inSupramolecular chemistry Vol. 15; no. 6; pp. 403 - 408
Main Authors Costero, Ana M., Pablo Villarroya, J., Gil, Salvador, Gaviña†, Pablo, Carmen Ramírez de Arellano, M.
Format Journal Article
LanguageEnglish
Published Taylor & Francis Group 01.09.2003
Subjects
Complexation
Conformational transmitter
Crown-ether
Cyclohexane
pH-switch
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Summary: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 1 H 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.
ISSN:1061-0278
1029-0478
DOI:10.1080/1061027031000116001