N-(Diisopropylthiophosphoryl)-N′-(R)-thioureas: Synthesis, characterization, crystal structures and competitive bulk liquid membrane transport of some metal ions
(2012) Dalton Transactions — Vol. 41, n° 11, p. 3223-3232 (2012)
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- Ten N-thiophosphorylated thioureas of the common formula RC(S)NHP(S)(OiPr) 2 [R = iPrNH (1), EtNH (2), Et 2N (3), 2,5-Me 2C 6H 3NH (4), 4-Me 2NC 6H 4NH (5), 2-MeO(O)CC 6H 4NH (6), 2-PyNH (7), 2-PyCH 2NH (8), 3-PyCH 2NH (9), cyclo-C 2H 2N 3NH (10)] have been synthesized and characterized by IR, NMR spectroscopy and elemental analysis. Molecular structures of 1 and 4-8 were elucidated by X-ray diffraction revealing linear, bi- or trifurcated intramolecular hydrogen bonds. Additionally, their crystal structures are stabillized by two intermolecular hydrogen bonds, which in turn lead to a centrosymmetric dimer formation. The hydrogen bonded dimers of 5-8 are packed to polymeric chains through the π⋯π stacking interactions between aryl or pyridyl rings. 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 2-6 and 8-10 as the ionophore present in the organic phase. The source phase contained equimolar concentrations of Co II, Ni II, Cu II, Zn II, Ag I, Cd II and Pb II with the source and receiving phases being buffered at pH = 5.5 and 1.0, respectively. The obtained data were compared with the transport and extraction properties of 1 and 7, which were described recently. © The Royal Society of Chemistry 2012.
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Babashkina, M. G., Safin, D., Bolte, M., & Garcia, Y. (2012). N-(Diisopropylthiophosphoryl)-N′-(R)-thioureas: Synthesis, characterization, crystal structures and competitive bulk liquid membrane transport of some metal ions. Dalton Transactions, 41(11), 3223-3232. https://doi.org/10.1039/c2dt11862a (Original work published 2012)