Abstract
Synthetic routes to four calix[4]arene stereoisomers with two distal methoxycarboxy groups and two distal butoxy groups are reported. Conformations of cone, partial cone (butyl up), partial cone (acid up), and 1,3-alternate were established by 1H and 13C-NMR spectroscopy. To probe the influence of ligand conformation on metal ion complexation, extractions from aqueous solutions into 1,2-dichloroethane were performed. These included competitive alkali metal cation extractions, competitive alkaline earth metal cation extractions, and single species extractions of Pb2+ and of Hg2+. Comparisons are also made with the results for a conformationally mobile analogue in which the two butoxy groups are replaced with methoxy groups.
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Acknowledgments
We thank the Division of Chemical Sciences, Geosciences, and Biosciences of the Office of Basic Energy Sciences of the U.S. Department of Energy (Grant DE-FG02-90ER14416) for support of this research. Dr. Vladimir S. Talanov provided important contributions to the development of viable synthetic routes to ligands 1–4.
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Park, C., Chun, S. & Bartsch, R.A. Effect of conformation on metal ion extraction by calix[4]arene dicarboxylic acids. J Incl Phenom Macrocycl Chem 66, 95–105 (2010). https://doi.org/10.1007/s10847-009-9650-6
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DOI: https://doi.org/10.1007/s10847-009-9650-6