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

Research output: Contribution to journalArticle

39 Citations (Scopus)

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 c intra and Tc inter 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
Externally publishedYes

Fingerprint

Crowns
Metal ions
Metals
Ions
Polyethers
Ion exchange
Ion Exchange
Temperature
Coulomb interactions
Static Electricity
Coalescence
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Crystal structure
Nuclear magnetic resonance
X-Rays
Oxygen
X rays
Atoms

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Rapid metal ions shuttling through 1,3-alternate thiacalix[4]crown tubes. / Lee, Jae Kwang; Kim, Sung Kuk; Bartsch, Richard A.; Vicens, Jacques; Miyano, Sotaro; Kim, Jong Seung.

In: Journal of Organic Chemistry, Vol. 68, No. 17, 01.09.2003, p. 6720-6725.

Research output: Contribution to journalArticle

Lee, JK, Kim, SK, Bartsch, RA, Vicens, J, Miyano, S & Kim, JS 2003, 'Rapid metal ions shuttling through 1,3-alternate thiacalix[4]crown tubes', Journal of Organic Chemistry, vol. 68, no. 17, pp. 6720-6725. https://doi.org/10.1021/jo034666y
Lee, Jae Kwang ; Kim, Sung Kuk ; Bartsch, Richard A. ; Vicens, Jacques ; Miyano, Sotaro ; Kim, Jong Seung. / Rapid metal ions shuttling through 1,3-alternate thiacalix[4]crown tubes. In: Journal of Organic Chemistry. 2003 ; Vol. 68, No. 17. pp. 6720-6725.
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