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Talanova GG, Talanov VS, Hwang HS, et al. Rigid versus flexible: how important is ligand "preorganization" for metal ion recognition by lower rim-functionalized calix[4]arenes?. Org Biomol Chem. 2004;2(18):2585-92doi: 10.1039/B407812H.
Talanova, G. G., Talanov, V. S., Hwang, H. S., Park, C., Surowiec, K., & Bartsch, R. A. (2004). Rigid versus flexible: how important is ligand "preorganization" for metal ion recognition by lower rim-functionalized calix[4]arenes?. Organic & biomolecular chemistry, 2(18), 2585-92. https://doi.org/10.1039/B407812H
Talanova, Galina G, et al. "Rigid versus flexible: how important is ligand "preorganization" for metal ion recognition by lower rim-functionalized calix[4]arenes?." Organic & biomolecular chemistry vol. 2,18 (2004): 2585-92. doi: https://doi.org/10.1039/B407812H
Talanova GG, Talanov VS, Hwang HS, Park C, Surowiec K, Bartsch RA. Rigid versus flexible: how important is ligand "preorganization" for metal ion recognition by lower rim-functionalized calix[4]arenes?. Org Biomol Chem. 2004 Sep 21;2(18):2585-92. doi: 10.1039/B407812H. Epub 2004 Aug 23. PMID: 15351822.
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Org Biomol Chem. 2004 Sep 21;2(18):2585-92. doi: 10.1039/B407812H. Epub 2004 Aug 23.

Rigid versus flexible: how important is ligand "preorganization" for metal ion recognition by lower rim-functionalized calix[4]arenes?.

Organic & biomolecular chemistry

Galina G Talanova, Vladimir S Talanov, Hong-Sik Hwang, Chunkyung Park, Kazimierz Surowiec, Richard A Bartsch

Affiliations

  1. Department of Chemistry, Howard University, 525 College Street, NW, Washington, DC 20059, USA. [email protected]

PMID: 15351822 DOI: 10.1039/B407812H

Abstract

For an assessment of the outcomes from use of an appropriately "preorganized" calixarene-based ionophore versus its conformationally mobile prototype, solvent extraction propensities of flexible calix[4]arene di-[N-(X-sulfonyl)carboxamides] for alkali, alkaline earth metal cations, Pb2+, Ag+ and Hg2+ are compared with those for seven new rigid analogs fixed in the cone, partial cone and 1,3-alternate conformations. For each of the metal ions, the preferred calix[4]arene conformation was determined from the NMR spectra for the metal salt of the flexible ligand. Except for Ag+, flexible calix[4]arene di-[N-(X-sulfonyl)carboxamides] were found to provide greater metal ion extraction efficiency and better selectivity than the corresponding "preorganized" ionophores.

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