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

Org Biomol Chem. 2011 May 7;9(9):3225-34. doi: 10.1039/c0ob01251c. Epub 2011 Mar 22.

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-Bu(4)NX (X = F(-), Cl(-), Br(-), I(-), CH(3)CO(2)(-), H(2)PO(4)(-), NO(3)(-)) 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 10(3)-10(5) 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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Anions / chemistry
  • Esters / chemistry*
  • Hydroxides / chemistry*
  • Molecular Structure
  • Phenols / chemistry*

Substances

  • Amides
  • Anions
  • Esters
  • Hydroxides
  • Phenols
  • p-tert-butylthiacalix(4)arene
  • hydroxide ion