Synthesis of a tetrahomodioxacalix[4]arene tetraamide and the crystal structure of its lead ion complex

K. H. No, J. S. Kim, O. J. Shon, S. H. Yang, I. H. Suh, J. G. Kim, R. A. Bartsch, J. Y. Kim

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Abstract

The 1,4-alternate tetrahomodioxacalix[4]arene tetraamide 4 with four p-phenyl groups on its upper rim was synthesized. In two-phase metal picrate extraction, 4 exhibited Pb2+ selectivity with formation of a 1:1 complex in chloroform. In the solid-state structure of the 4·Pb(Pic)2 complex, Pb2+ is bound by the carbonyl oxygens of two adjacent amide groups and an aryl-alkyl ether oxygen atom of one of these amide-containing substituents. The crystal structure and 1H NMR spectrum of the 4·Pb2+ complex reveals π-metal ion complexation of one aromatic ring in the ligand with Pb2+.

Original languageEnglish
Pages (from-to)5976-5980
Number of pages5
JournalJournal of Organic Chemistry
Volume66
Issue number18
DOIs
Publication statusPublished - 2001 Sep 7

ASJC Scopus subject areas

  • Organic Chemistry

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    No, K. H., Kim, J. S., Shon, O. J., Yang, S. H., Suh, I. H., Kim, J. G., Bartsch, R. A., & Kim, J. Y. (2001). Synthesis of a tetrahomodioxacalix[4]arene tetraamide and the crystal structure of its lead ion complex. Journal of Organic Chemistry, 66(18), 5976-5980. https://doi.org/10.1021/jo0101656