A series of tetrahomodioxacalix[4]biscrown-n. syntheses, crystal structures, and metal binding abilities

Kwanghyun No; Han Bok Ju; Hwan Suh Il; Ook Kang Sang; Jaejung Ko; Chun Nam Kye; Seung Kim Jong

doi:10.1021/jo049107l

A series of tetrahomodioxacalix[4]biscrown-n. syntheses, crystal structures, and metal binding abilities

Kwanghyun No, Han Bok Ju, Hwan Suh Il, Ook Kang Sang, Jaejung Ko, Chun Nam Kye, Seung Kim Jong

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

Abstract

A series of novel tetrahomodioxacalix[4]biscrowns with crown-2, crown-3, crown-4, crown-5, and crown-6 units were synthesized. Conformations of each product are dependent on the base used and their conformation stabilities. All conformations were proven by NMR spectra and/or X-ray crystal structures. The 1,3-alternate homodioxacalix[4]-biscrown-4 (4b) shows the best selectivity for K⁺, whereas the 1,3-alternate homodioxacalix[4] crown-5 (5) does for Cs⁺. Those selectivities are attributable to electrostatic interaction between the metal ion and the crown ring, as well as a π-metal complexation. However, the C-1,2-alternate conformation does not take the metal ions regardless of the crown species as a result of steric hindrance from the methylene bridge of an ArCH₂Ar unit.

Original language	English
Pages (from-to)	6938-6941
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	69
Issue number	20
DOIs	https://doi.org/10.1021/jo049107l
Publication status	Published - 2004 Oct 1
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "A series of tetrahomodioxacalix[4]biscrown-n. syntheses, crystal structures, and metal binding abilities",

abstract = "A series of novel tetrahomodioxacalix[4]biscrowns with crown-2, crown-3, crown-4, crown-5, and crown-6 units were synthesized. Conformations of each product are dependent on the base used and their conformation stabilities. All conformations were proven by NMR spectra and/or X-ray crystal structures. The 1,3-alternate homodioxacalix[4]-biscrown-4 (4b) shows the best selectivity for K+, whereas the 1,3-alternate homodioxacalix[4] crown-5 (5) does for Cs+. Those selectivities are attributable to electrostatic interaction between the metal ion and the crown ring, as well as a π-metal complexation. However, the C-1,2-alternate conformation does not take the metal ions regardless of the crown species as a result of steric hindrance from the methylene bridge of an ArCH2Ar unit.",

author = "Kwanghyun No and Ju, {Han Bok} and Il, {Hwan Suh} and Sang, {Ook Kang} and Jaejung Ko and Kye, {Chun Nam} and Jong, {Seung Kim}",

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T1 - A series of tetrahomodioxacalix[4]biscrown-n. syntheses, crystal structures, and metal binding abilities

AU - No, Kwanghyun

AU - Ju, Han Bok

AU - Il, Hwan Suh

AU - Sang, Ook Kang

AU - Ko, Jaejung

AU - Kye, Chun Nam

AU - Jong, Seung Kim

PY - 2004/10/1

Y1 - 2004/10/1

N2 - A series of novel tetrahomodioxacalix[4]biscrowns with crown-2, crown-3, crown-4, crown-5, and crown-6 units were synthesized. Conformations of each product are dependent on the base used and their conformation stabilities. All conformations were proven by NMR spectra and/or X-ray crystal structures. The 1,3-alternate homodioxacalix[4]-biscrown-4 (4b) shows the best selectivity for K+, whereas the 1,3-alternate homodioxacalix[4] crown-5 (5) does for Cs+. Those selectivities are attributable to electrostatic interaction between the metal ion and the crown ring, as well as a π-metal complexation. However, the C-1,2-alternate conformation does not take the metal ions regardless of the crown species as a result of steric hindrance from the methylene bridge of an ArCH2Ar unit.

AB - A series of novel tetrahomodioxacalix[4]biscrowns with crown-2, crown-3, crown-4, crown-5, and crown-6 units were synthesized. Conformations of each product are dependent on the base used and their conformation stabilities. All conformations were proven by NMR spectra and/or X-ray crystal structures. The 1,3-alternate homodioxacalix[4]-biscrown-4 (4b) shows the best selectivity for K+, whereas the 1,3-alternate homodioxacalix[4] crown-5 (5) does for Cs+. Those selectivities are attributable to electrostatic interaction between the metal ion and the crown ring, as well as a π-metal complexation. However, the C-1,2-alternate conformation does not take the metal ions regardless of the crown species as a result of steric hindrance from the methylene bridge of an ArCH2Ar unit.

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A series of tetrahomodioxacalix[4]biscrown-n. syntheses, crystal structures, and metal binding abilities

Abstract

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