Synthesis of a Tetrahomodioxacalix[4]arene Tetraamide and the Crystal Structure of Its Lead Ion Complex

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 bo...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-09, Vol.66 (18), p.5976-5980
Main Authors: No, Kwang H, Kim, Jong S, Shon, Ok J, Yang, Seung H, Suh, Il H, Kim, Jin G, Bartsch, Richard A, Kim, Jong Y
Format: Article
Language:English
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Summary: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+.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0101656