p-tert-Butyl thiacalix[4]arenes functionalized at the lower rim by amide, hydroxyl and ester groups as anion receptors?

Organic & Biomolecular Chemistry Pub Date: 2011-02-17 DOI: 10.1039/C0OB01251C

Abstract

New p-tert-butyl thiacalix[4]arenes differently substituted at the lower rim with amide, hydroxyl and ester groups were synthesized. Binding properties of the compounds toward some tetrabutylammonium salts n-Bu4NX (X = F?, Cl?, Br?, I?, CH3CO2?, H2PO4?, NO3?) were studied by UV spectroscopy. It was found that the stoichiometry of the complexes, generally, is 1?:?1, and the association constants are in the range of 103–105 M?1. The p-tert-butyl thiacalix[4]arenes containing secondary amide groups trisubstituted at the lower rim bind the studied anions most effectively. Selective receptors for fluoride and dihydrogen phosphate salts of tetrabutylammonium were found.

Graphical abstract: p-tert-Butyl thiacalix[4]arenes functionalized at the lower rim by amide, hydroxyl and ester groups as anion receptors
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