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Lipophilic cage ligands: Synthesis spectroscopic properties and applications

Pure and Applied Chemistry, ISSN: 1365-3075, Vol: 58, Issue: 11, Page: 1503-1510
1986
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Metrics Details

  • Citations
    10
    • Citation Indexes
      10
  • Captures
    2

Article Description

Macropolycyclic lipophilic ligands, capable of solubilizing inorganic salts in non polar organic solvents, can be efficiently used as anion activators or ion carriers through membranes. In this context we recently reported the synthesis of new 1ipophi1ic ligands 6 assisted by the template effect of sodium cation. Due to the high rigidity imposed by the short bridging chains ligands 6 form very stable sodium complexes in non-polar media, even when very hydrophilic and poorly polarizable anions are involved. This makes it easy to perform base-promoted reactions: e.g. carbanion formation from very weak carbon acids under phase-transfer conditions. X-Ray analysis of a sodium perchlorate complex showed that the cation is embedded in a non-symmetric cubic cage. The assignment of all resonances of H and C NMR spectra was achieved by using two-dimensional techniques. At room temperature the free ligand is in a fast conformational equilibrium as shown by a C NMR investigation at variable temperature. However, in the sodium perchlorate complex only the portion of the molecule on the side of the alkyl group is affected by lowering the temperature, while the remaining part showed no conformational change down to -60°C. Ligands 6 were obtained by continuous extraction with n-hexane from an aqueous solution of their methoxide or fluoride sodium complexes. This allowed the preparation and the study of complexes with different metal cations, as K, Ag, Cu etc. © 1986 IUPAC

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