Issue 11, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

New mono-ionizable, Li+-selective calix[4]arenes

Galina G. Talanova,†a   Vladimir S. Talanov,a   Hong-Sik Hwang,a   Bijan A. Eliasib  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

b Crompton Corporation, Crop Protection Research and Development, 199 Benson Road, Middlebury, Connecticut, USA

Abstract

A series of new mono-ionizable cone calix[4]arenes, with either a pendent carboxylic acid or a N-(X-sulfonyl)carboxamide group, is synthesized and their alkali metal cation extraction behavior determined and compared with that for conformationally mobile analogues. These new proton-ionizable, cone calixarenes exhibit good (for the sulfonylcarboxamides) to excellent (for the carboxylic acid) Li+-selectivity. Surprisingly, the Li+-selectivity decreases on going from the conformationally flexible to the cone ionophores due to enhanced Na+ binding by the latter. During the ligand synthesis, unusual behavior of cone tributoxy-N-(trifluoromethylsulfonyl)carbamoylmethoxy-p-tert-butylcalix[4]arene suggests a strong tendency for molecular association.

Graphical abstract: New mono-ionizable, Li+-selective calix[4]arenes

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Article information

DOI
https://doi.org/10.1039/B206484G
Article type
Paper
Submitted
05 Jul 2002
Accepted
08 Aug 2002
First published
17 Sep 2002

J. Chem. Soc., Perkin Trans. 2, 2002, 1869-1874

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New mono-ionizable, Li+-selective calix[4]arenes

G. G. Talanova, V. S. Talanov, H. Hwang, B. A. Eliasi and R. A. Bartsch, J. Chem. Soc., Perkin Trans. 2, 2002, 1869 DOI: 10.1039/B206484G

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