A Convenient Synthesis of New Macrocyclic Thioether-Esters and Ether-Esters: Extraction Properties of These Esters for Alkali, Alkaline Earth, and Transition Metal Cations

Macrocyclic thioether-esters and ether-esters have been prepared by treating 2,2′-dithiobenzoic acid dichloride and 1,2-benzendicarboxylic acid dichloride with appropriate glycols or dithiol. The complexing ability of these thioether-esters and ether-esters toward Li⁺, Na⁺, K⁺, Mg ^{2 +} , Ca ^{2 +} , Sr ²⁺ , Ba ^{2 +} , Co ^{2 +} , and Ni ^{2 +} has been measured by the solvent extraction method. The extraction data indicate that compound 2 exhibits stronger selectivity toward Li⁺, 3 toward Ba ^{2 +} , 4 toward K⁺, 5 toward Mg ^{2 +} , 6 toward Ba ^{2 +} and Sr ^{2 +} , and 7 toward Co ^{2 +} and Ni ^{2 +} when compared with other cations.

Notes

^a Average for three samples.

^b Organic phase (dichloromethane): (2–7 macrocycles) = 7.0 × 10^{− 4} M. Aqueous phase: (picric acid) = 7.0 × 10^{− 4} alkali, alkaline earth metal chloride; (transition metal hydroxide) = 0.1 M