Rapid metal ions shuttling through 1,3-alternate thiacalix[4]crown tubes

Jae Kwang Lee, Sung Kuk Kim, Richard A. Bartsch, Jacques Vicens, Sotaro Miyano, Jong Seung Kim

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Abstract

Several new thiacalix[4]monocrown and thiacalix[4]biscrown compounds were synthesized. Their metal ion extractabilities are found to be lower than those of conventional calix[4]crowns. By use of X-ray crystal structures and 1H NMR spectroscopy, this result is explained by weaker electrostatic interactions of the polyether ring oxygen atoms with the metal ions and diminished π-metal ion interactions between the metal ions and the aromatic rings of the thiacalix[4]crowns. Temperature-dependent 1H NMR spectroscopic measurements reveal coalescence temperatures T cintra and Tcinter for metal ion exchange. In one case, this exchange was rationalized as metal ion shuttling through a thiacalix[4]biscrown tube. Since the metal ions are less tightly complexed by the polyether units in thiacalix[4]biscrowns than in conventional calix[4]biscrowns, more facile metal ion exchange between the two polyether units takes place in the former.

Original languageEnglish
Pages (from-to)6720-6725
Number of pages6
JournalJournal of Organic Chemistry
Volume68
Issue number17
DOIs
Publication statusPublished - 2003 Sep 1

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ASJC Scopus subject areas

  • Organic Chemistry

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