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

Authors
No, KBok, JHSuh, IHKang, SOKo, JNam, KCKim, JS
Issue Date
Oct-2004
Publisher
AMER CHEMICAL SOC
Citation
JOURNAL OF ORGANIC CHEMISTRY, v.69, no.20, pp 6938 - 6941
Pages
4
Journal Title
JOURNAL OF ORGANIC CHEMISTRY
Volume
69
Number
20
Start Page
6938
End Page
6941
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/15821
DOI
10.1021/jo049107l
ISSN
0022-3263
1520-6904
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 pi-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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