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

J Org Chem. 2001 Sep 7;66(18):5976-80. doi: 10.1021/jo0101656.

Authors

K H No¹, J S Kim, O J Shon, S H Yang, I H Suh, J G Kim, R A Bartsch, J Y Kim

Affiliation

¹ Department of Chemistry, Sookmyung Women's University, Seoul 140-742, Korea.

PMID: 11529720
DOI: 10.1021/jo0101656

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 pi-metal ion complexation of one aromatic ring in the ligand with Pb2+.