Thiophosphorylated bis-thioureas for competitive bulk liquid membrane transport of some metal ions

Abstract

Eight N-thiophosphorylated bis-thioureas of the common formula Z[NHC(S)NHP(S)(OiPr) 2] 2 [Z = (1), 1,2-C 6H 4 (2), 1,3-C 6H 4 (3), 1,4-C 6H 4 (4), CH 2(1,4-C 6H 4) 2 (5), O(1,4-C 6H 4) 2 (6), S(1,4-C 6H 4) 2 (7), CH 2(1,4-C 6H 10) 2 (8)] have been synthesized and characterized by NMR spectroscopy and elemental analysis. Molecular structures of 3, 4, 5·0.5C 6H 14, 6·CH 2Cl 2 and 8 were elucidated by X-ray diffraction revealing two linear intramolecular hydrogen bonds. Their crystal structures are stabilized by four intermolecular hydrogen bonds, which in turn lead to a polymeric chain formation. Competitive transport experiments involving metal ions from an aqueous source phase through a chloroform membrane into an aqueous receiving phase have been carried out using 1-8 as the ionophore present in the organic phase. © 2012 The Royal Society of Chemistry.