Calixarenes Derivatized with Sulfur-Containing Functionalities as Selective Extractants for Heavy and Precious Metal Ions

Alexander T. Yordanov; Bruce R. Whittlesey; D. Max Roundhill

doi:10.1021/ic9709988

Calixarenes Derivatized with Sulfur-Containing Functionalities as Selective Extractants for Heavy and Precious Metal Ions

Inorg Chem. 1998 Jul 13;37(14):3526-3531. doi: 10.1021/ic9709988.

Authors

Alexander T. Yordanov¹, Bruce R. Whittlesey, D. Max Roundhill

Affiliation

¹ Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061.

PMID: 11670438
DOI: 10.1021/ic9709988

Abstract

The calix[4]arenes 5,11,17,23-tert-butyl-25,26,27,28-(2-methylthioethoxy)calix[4]arene, 25,26,27,28-(2-methylthioethoxy)calix[4]arene, and 5,11,17,23-tert-butyl-25,26,27,28-(2-(2-thiophenecarboxy)ethoxy)calix[4]arene have been prepared. The structure of 25,26,27,28-(2-methylthioethoxy)calix[4]arene has been verified by X-ray crystallography. The crystals with the empirical formula C(40)H(48)O(4)S(4) are monoclinic C2/c with a = 20.428(2) Å, b = 10.581(1) Å, c = 20.445(2) Å, beta = 118.461(5) degrees, Z = 4. These calix[4]arenes are effective extractants for transferring heavy metal ions from aqueous solution into chloroform. The extraction of Sn(II), Hg(II), Ag(I), Pd(II), Au(III), MeHg(II), Pb(II) and Cd(II) into chloroform with these calix[4]arenes is compared with that performed with 5,11,17,23-tert-butyl-25,26,27,28-(2-N,N-dimethyldithiocarbamoylethoxy)calix[4]arene, 25,26,27,28-(2,N,N-dimethyldithiocarbamoylethoxy)calix[4]arene, and 5,11,17,23-tert-butyl-25,26,27,28-(2-mercaptoethoxy)calix[4]arene.