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N-(Diisopropylthiophosphoryl)-N′-(R)-thioureas: Synthesis, characterization, crystal structures and competitive bulk liquid membrane transport of some metal ions

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Babashkina, M.G. [UCL] Safin, Damir [UCL] Bolte, M. [J.-W.-Goethe-Universitat, Frankfurt-Main (Germany)] Garcia, Yann [UCL]

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.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2012
Language Anglais
Journal information "Dalton Transactions" - Vol. 41, no.11, p. 3223-3232 (2012)
Peer reviewed yes
Publisher The Royal Society of Chemistry
issn 1477-9226
Publication status Publié
Affiliation UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
Keywords Bulk liquid membrane ; Pyridyl rings ; Stacking interaction ; Transport experiments ; Dimers ; Hydrogen bonds ; Lead ; Liquid membranes ; Metal ions ; Nuclear magnetic resonance spectroscopy ; X ray diffraction ; Centrosymmetric dimers ; Thioureas ; Equimolar concentrations ; Extraction properties ; Hydrogen-bonded dimers ; Intermolecular hydrogen bonds ; Intramolecular hydrogen bond ; Organic phase ; Polymeric chain
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Bibliographic reference Babashkina, M.G. ; Safin, Damir ; Bolte, M. ; Garcia, Yann. N-(Diisopropylthiophosphoryl)-N′-(R)-thioureas: Synthesis, characterization, crystal structures and competitive bulk liquid membrane transport of some metal ions . In: Dalton Transactions, Vol. 41, no.11, p. 3223-3232 (2012)
Permanent URL http://hdl.handle.net/2078.1/125491