Issue 15, 2006
From the journal:

Organic & Biomolecular Chemistry

Di-ionizable p-tert-butylcalix[4]arene-1,2-crown-5 and -crown-6 compounds in the cone conformation: synthesis and alkaline earth metalcationextraction

Chuqiao Tu,a   Dazhan Liu,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

Di-ionizable p-tert-butylcalix[4]arene-1,2-crown-5 and -crown-6 ethers in the cone conformation were prepared and their conformations and regioselectivities were verified by NMR spectroscopy. The metal ion-complexing properties of these ligands were evaluated by competitive solvent extractions of alkaline earth metal cations from water into chloroform. The ligands were found to be efficient extractants with selectivity for Ba2+. The maximal loadings were 95–100% as calculated for formation of 1 : 1 ionized ligand–metal ion complexes. With the variation of proton-ionizable groups, which were oxyacetic acid moieties and N-(X)sulfonyl oxyacetamide units with X = methyl, phenyl, 4-nitrophenyl, and trifluoromethyl, “tunable” acidity was obtained.

Graphical abstract: Di-ionizable p-tert-butylcalix[4]arene-1,2-crown-5 and -crown-6 compounds in the cone conformation: synthesis and alkaline earth metal cation extraction

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Article information

DOI
https://doi.org/10.1039/B604218J
Article type
Paper
Submitted
15 May 2006
Accepted
15 Jun 2006
First published
30 Jun 2006

Org. Biomol. Chem., 2006,4, 2938-2944

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Di-ionizable p-tert-butylcalix[4]arene-1,2-crown-5 and -crown-6 compounds in the cone conformation: synthesis and alkaline earth metal cation extraction

C. Tu, D. Liu, K. Surowiec, D. W. Purkiss and R. A. Bartsch, Org. Biomol. Chem., 2006, 4, 2938 DOI: 10.1039/B604218J

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