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<p>1,5-Bis(2′-acetylphenoxy)pentane, bis(2′-acetylphenoxy)diethyl ether, and 1,10-bis(2′-acetylphenoxy)decane were synthesized by the alkylation of 2′-hydroxyacetophenone with α,ω-dihaloalkanes. Based on these compounds, α,ω-[bis(2′-trifluoroacetoacetylphenoxy)]-alkanes were prepared by the treatment of diketones with ethyl trifluoroacetate in the presence of lithium hydride. The structures of the synthesized compounds were confirmed and their conformational differences were revealed by X-ray diffraction analysis. The evaluation of the selectivity of interactions of the α,ω-bis(2′-acetylphenoxy) and α,ω-bis(2′-trifluoroacetoacetylphenoxy) derivatives with a full range of alkali metal ions demonstrated an increase in the static exchange capacity with a simultaneous decrease in the selectivity of the interaction when replacing the carbon atom in the 3 position with an oxygen atom in the pentamethylene linker. A similar situation is observed in the case of a twofold increase in the size of the linker from pentamethylene to decamethylene. In the series of α,ω-bis(2′-trifluoroacetoacetylphenoxy) derivatives, the same changes in the structure of the linker lead to a decrease in the reactivity of the chelating ligand, facilitating the increase in the selectivity of the interaction with cesium ions.</p>

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Synthesis of a series of bis(2′-trifluoroacetoacetylphenoxy) derivatives and their chelating ability toward alkali metal ions

  • 期刊论文

  • 发表日期：

    2025年3月1日

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  • A. N. Patrina,
  • E. A. Veretennikova,
  • L. A. Khamidullina,
  • I. S. Puzyrev,
  • P. A. Slepukhin,
  • E. F. Zhilina,
  • M. A. Ezhikova,
  • M. I. Kodess,
  • A. V. Pestov

摘要

1,5-Bis(2′-acetylphenoxy)pentane, bis(2′-acetylphenoxy)diethyl ether, and 1,10-bis(2′-acetylphenoxy)decane were synthesized by the alkylation of 2′-hydroxyacetophenone with α,ω-dihaloalkanes. Based on these compounds, α,ω-[bis(2′-trifluoroacetoacetylphenoxy)]-alkanes were prepared by the treatment of diketones with ethyl trifluoroacetate in the presence of lithium hydride. The structures of the synthesized compounds were confirmed and their conformational differences were revealed by X-ray diffraction analysis. The evaluation of the selectivity of interactions of the α,ω-bis(2′-acetylphenoxy) and α,ω-bis(2′-trifluoroacetoacetylphenoxy) derivatives with a full range of alkali metal ions demonstrated an increase in the static exchange capacity with a simultaneous decrease in the selectivity of the interaction when replacing the carbon atom in the 3 position with an oxygen atom in the pentamethylene linker. A similar situation is observed in the case of a twofold increase in the size of the linker from pentamethylene to decamethylene. In the series of α,ω-bis(2′-trifluoroacetoacetylphenoxy) derivatives, the same changes in the structure of the linker lead to a decrease in the reactivity of the chelating ligand, facilitating the increase in the selectivity of the interaction with cesium ions.