Synthesis of bis(amidoxime)s and evaluation of their properties as uranyl-complexing agents

Uranium pollution involves high toxicity and radioactivity and, therefore, constitutes a grave threat to human health and the environment. Chelation is an effective method for sequestering uranium. It is well known that chelators based on oxime groups are able to complex uranyl cations efficiently....

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Bibliographic Details
Published in:Tetrahedron 2018-05, Vol.74 (21), p.2641-2649
Main Authors: Stemper, Jérémy, Tuo, Wei, Mazarío, Eva, Helal, Ahmed S., Djurovic, Alexandre, Lion, Claude, El Hage Chahine, Jean-Michel, Maurel, François, Hémadi, Miryana, Le Gall, Thierry
Format: Article
Language:English
Subjects:
Affinity constant
Amidoxime
Chemical Sciences
Metal complexation
Synthesis
Uranyl
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Summary:Uranium pollution involves high toxicity and radioactivity and, therefore, constitutes a grave threat to human health and the environment. Chelation is an effective method for sequestering uranium. It is well known that chelators based on oxime groups are able to complex uranyl cations efficiently. To this end, various bis(amidoxime)s were synthesized by reaction of hydroxylamine with the corresponding dinitriles. In these compounds the amidoximes are separated by chains of various lengths, some including a heterocycle (pyridine or 1,3,5-triazine). The abilities of these bis(amidoxime)s to complex uranyl cation in water were evaluated by determining their affinity constants and thermodynamic parameters by means of Isothermal Titration Calorimetry (ITC). DFT calculations were also performed, to determine the optimum structures of the complexes formed between uranyl cations and the oximate groups. A tetrakis(amidoxime), also synthesized in this work, shows good affinity for uranium, and a single molecule is able chelate several uranyl cations. These results are of importance for the remediation of uranium-polluted wastewaters, and open up several perspectives for the design and synthesis of new amidoxime compounds. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.04.016