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

doi:10.1021/jo0101656

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 language	English
Pages (from-to)	5976-5980
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	66
Issue number	18
DOIs	https://doi.org/10.1021/jo0101656
Publication status	Published - 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

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

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+.",

author = "No, {K. H.} and Kim, {J. S.} and Shon, {O. J.} and Yang, {S. H.} and Suh, {I. H.} and Kim, {J. G.} and Bartsch, {R. A.} and Kim, {J. Y.}",

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AU - No, K. H.

AU - Kim, J. S.

AU - Shon, O. J.

AU - Yang, S. H.

AU - Suh, I. H.

AU - Kim, J. G.

AU - Bartsch, R. A.

AU - Kim, J. Y.

PY - 2001/9/7

Y1 - 2001/9/7

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AB - 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+.

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