Sulphur-enriched thiacalix[4]arenes in the cone conformation: synthesis, crystal structures and cation binding properties |
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Authors: | Saliha Bouhroum Jong Seung Kim Soon W Lee Pierre Thuéry Glenn Yap Françoise Arnaud-Neu Jacques Vicens |
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Institution: | 1. Département des Sciences Analytiques, Institut Pluridisciplinaire Hubert Curien, ULP, CNRS, ECPM, 25, rue Becquerel, 67087, Strasbourg, France 2. Department of Chemistry, Korea University, Seoul, Republic of Korea 3. Department of Chemistry, Sungyunkwan University, Suwon, 440-746, Republic of Korea 4. CEA Saclay, DSM/IRAMIS/SCM (CNRS URA 331), 91191, Gif-sur-Yvette, France 5. 201 Brown Laboratory, Department of Chemistry & Biochemistry, University of Delaware, Newark, DE, 19716, USA
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Abstract: | The synthesis and crystal structure of p-tert-butylthia- and p-tert-butylcalix4]arene derivatives 1–7 substituted at the narrow rim by diethylthiophosphate ester groups, -PS(OEt)2 are reported. In these compounds the phosphorus atoms are directly attached to the phenolic O atoms of the calix units and the S atoms of the thiophosphate may serve as a two-electron donor to a metal ion. Their crystal structures were solved, which revealed their cone conformation. Their cation-binding properties have been established by liquid-liquid extraction of metal picrates from water into dichloromethane and stability constant determination in acetonitrile using UV-absorption spectrophotometry. Quantitative extraction was achieved for Ag+ (%E = 99) with the tetra-substituted thiacalix4]arene derivative. The complexes were found to be of 1:1 stoichiometry and the location of the metal cations was shown to be nearby the sulphur atoms by 1H NMR. |
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