Issue 2, 2007
From the journal:

Organic & Biomolecular Chemistry

Effect of para-substituents on alkaline earth metal ion extraction by proton di-ionizable calix[4]arene-crown-6 ligands in cone, partial-cone and 1,3-alternate conformations

Hui Zhou,a   Dazhan Liu,a   Jerzy Gega,a   Kazimierz Surowiec,a   David W. Purkissa  and  Richard A. Bartsch*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, USA
E-mail: richard.bartsch@ttu.edu
Fax: +1(806) 742 1289
Tel: +1(806) 742 3069

Abstract

Two carboxylic acid or N-(X)sulfonyl carboxamide groups were incorporated into calix[4]arene-crown-6 compounds to afford di-ionizable ligands for use in divalent metal ion separations. Acidities of the N-(X)sulfonyl carboxamide groups were tuned by variation of the electron-withdrawing properties of X. Cone, partial-cone and 1,3-alternate conformations were obtained by different synthetic strategies and their structures verified by NMR spectroscopy. Competitive solvent extractions of alkaline earth metal cations from aqueous solutions into chloroform were performed and the results compared with those reported previously for di-ionizable p-tert-butylcalix[4]arene-crown-6 analogues to probe the influence of the para-substituent on the calix[4]arene scaffold on extraction selectivity and efficiency.

Graphical abstract: Effect of para-substituents on alkaline earth metal ion extraction by proton di-ionizable calix[4]arene-crown-6 ligands in cone, partial-cone and 1,3-alternate conformations

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Article information

DOI
https://doi.org/10.1039/B611570E
Article type
Paper
Submitted
10 Aug 2006
Accepted
08 Nov 2006
First published
24 Nov 2006

Org. Biomol. Chem., 2007,5, 324-332

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Effect of para-substituents on alkaline earth metal ion extraction by proton di-ionizable calix[4]arene-crown-6 ligands in cone, partial-cone and 1,3-alternate conformations

H. Zhou, D. Liu, J. Gega, K. Surowiec, D. W. Purkiss and R. A. Bartsch, Org. Biomol. Chem., 2007, 5, 324 DOI: 10.1039/B611570E

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