Sulphur-enriched thiacalix[4]arenes in the cone conformation: Synthesis, crystal structures and cation binding properties

Saliha Bouhroum, Jong Seung Kim, Soon W. Lee, Pierre Thuéry, Glenn Yap, Françoise Arnaud-Neu, Jacques Vicens

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The synthesis and crystal structure of p-tert-butylthia- and p-tert-butylcalix[4]arene derivatives 1-7 substituted at the narrow rim by diethylthiophosphate ester groups, -PS(OEt)2 are reported. In these compounds the phosphorus atoms are directly attached to the phenolic O atoms of the calix units and the S atoms of the thiophosphate may serve as a two-electron donor to a metal ion. Their crystal structures were solved, which revealed their cone conformation. Their cation-binding properties have been established by liquid-liquid extraction of metal picrates from water into dichloromethane and stability constant determination in acetonitrile using UV-absorption spectrophotometry. Quantitative extraction was achieved for Ag+ (%E = 99) with the tetra-substituted thiacalix[4]arene derivative. The complexes were found to be of 1:1 stoichiometry and the location of the metal cations was shown to be nearby the sulphur atoms by 1H NMR.

Original languageEnglish
Pages (from-to)239-250
Number of pages12
JournalJournal of Inclusion Phenomena and Macrocyclic Chemistry
Volume62
Issue number3-4
DOIs
Publication statusPublished - 2008 Dec

Keywords

  • Conformation
  • Diethylthiophosphate ester
  • Metal complexation
  • Thiacalixarenes
  • X-ray structures

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Condensed Matter Physics

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