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Macrocyclic 14-Membered Ring Diketal Dilactams: Evaluation of their Divalent Cation Binding Properties

, , , , &
Pages 261-269 | Received 04 Mar 2002, Accepted 09 Sep 2002, Published online: 27 Apr 2017
 

Abstract

The binding abilities of a new class of 14-membered ring ligands bearing diketal dilactam functions were explored by UV-visible spectrophotometry. Their formation constants, determined in THF solution, showed appreciable complexation with divalent cations (stability order: Sr2+≥Ca2+>Zn2+≥Mg2+>Ba2+) whereas no association was observed with monovalent cations. The stoichiometry of the complexes formed was essentially 1:1 although sometimes a low percentage (<10%) of 1:2 (cation–ligand) species was detected. The corresponding formation constants determined by computation (STAR program) were in the range 1.5<log β 11<4.8 and 4.4<log β 12<7.1. They depend significantly on the nature of the substituents. In addition, solvent extractions carried out in a water–chloroform system showed the highest constants (log K ex) for the most substituted macrocycles 7b and 7c (norephedrine series) with a lipophilic skeleton.

Acknowledgements

The authors thank M. Cochet and E. Perfetti for technical assistance.

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