Tripodal (N-alkylated) CMP(O) and malonamide ligands: synthesis, extraction of metal ions, and potentiometric studies

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Janczewski, Dominik and Reinhoudt, David N. and Verboom, Willem and Malinowska, Elzbieta and Pietrzak, Mariusz and Hill, Clement and Allignol, Cecile (2007) Tripodal (N-alkylated) CMP(O) and malonamide ligands: synthesis, extraction of metal ions, and potentiometric studies. New Journal of Chemistry, 31 (1). pp. 109-120. ISSN 1144-0546

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Abstract:Tripodal ligands build on the C-pivot ( 9b–e, 13b–d, and 17a–d) and trialkylbenzene platforms ( 10a,b, 11, 12, 14a,b, and 18a,b) bearing (N-alkylated) carbamoylmethylphosphine oxide (CMPO), carbamoylmethylphosphonate (CMP), and malonamide moieties were synthesized. Extraction studies with Am3+ and Eu3+ show that in general there is a positive influence of the N-alkyl substituents in C-pivot CMP(O) ligands on the D(distribution) coefficients. The trialkylbenzene CMPO ligands 10a,b, 11, and 12 have considerably larger D coefficients than the corresponding C-pivot analogues 9a–e, although hardly having any selectivity, while N-alkylation gives rise to smaller D coefficients. Although less effective the extraction behavior of the C-pivot CMP analogues 13b–d shows more or less the same trend as the corresponding CMPO ligands 9b–e upon substitution of the carboxamide N-atom with different alkyl chains. The different malonamide ligands 17a–d and 18a,b are bad extractants, while N-alkylation makes them even worse. Potentiometric studies of CMP(O) and malonamide ligands in polymeric membranes on Pb2+, Cu2+, Ca2+, Mg2+, Na+, and K+ salts revealed that N-alkyl substituents increase the stability constants of ion–ionophore complexes compared to unsubstituted ligands. In polymeric membrane electrodes the ligands induce a selectivity pattern that differs significantly from the so-called Hofmeister series, giving the highest selectivity coefficients for UO22+ among all examined cations (Pb2+, Cu2+, Ca2+, Mg2+, Na+, K+).
Item Type:Article
Copyright:© 2007 Royal Society of Chemistry
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/60355
Official URL:http://dx.doi.org/10.1039/b613254e
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Metis ID: 241357