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Remarkably Selective Ag(+) Extraction and Transport by Thiolariat Ethers.

Tatsuya Nabeshima1, Naoko Tsukada, Katsunori Nishijima

  • 1Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki 305, Japan and Department of Chemistry, Gunma University, Kiryu, Gunma 376, Japan.

The Journal of Organic Chemistry
|June 26, 1996
PubMed
Summary

Thiolariat ethers with a 15-crown-5 ring exhibit remarkable selectivity for silver ions (Ag+), outperforming other crown ether derivatives in metal binding. This selectivity arises from the synergistic coordination of ring oxygen and sulfur atoms.

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Area of Science:

  • Supramolecular chemistry
  • Coordination chemistry
  • Analytical chemistry

Background:

  • Crown ethers are known for their ability to bind metal ions.
  • Introducing a sulfide side chain into a crown ether framework creates thiolariat ethers.
  • Understanding selective metal ion binding is crucial for various applications.

Purpose of the Study:

  • To synthesize and investigate the metal binding properties of thiolariat ethers.
  • To evaluate the selectivity of thiolariat ethers for specific heavy metal ions, particularly silver.
  • To elucidate the structural basis for selective silver ion binding.

Main Methods:

  • Solvent extraction experiments were conducted using various thiolariat ether derivatives.
  • Liquid membrane transport studies were performed to assess ion mobility.

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  • Nuclear Magnetic Resonance (NMR) spectroscopy was employed to study complexation.
  • Job plot analysis was used to determine complex stoichiometry.

    • Main Results:

    • Thiolariat ethers with a 15-crown-5 ring demonstrated exceptionally high selectivity for silver ions (Ag+) among heavy metal ions.
    • Thiolariat ethers with 12-crown-4 or 18-crown-6 rings showed lower or no selectivity for Ag+.
    • Oxygen analogs (lariat ethers) and oxidized sulfur analogs (sulfoxide, sulfone) lacked Ag+ selectivity.
    • Benzocrown-based thiolariat ethers exhibited very low affinity for Ag+.
    • Synergistic coordination between the crown ether oxygen and the sulfur atom was identified as the key factor for high Ag+ selectivity.
    • NMR studies confirmed the proposed synergistic coordination and 1:1 complexation between thiolariat ether and Ag+.

    Conclusions:

    • Thiolariat ethers, particularly those incorporating a 15-crown-5 ring, are highly effective and selective carriers for silver ions.
    • The unique structure featuring both crown ether oxygen and a sulfide sulfur atom enables synergistic coordination, driving Ag+ selectivity.
    • These findings offer potential for developing novel materials for silver ion separation and detection.