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Lower rim substituted p-tert-butyl calix[4]arene; Part 14. Synthesis, structures and binding studies of calix[4]arene thioamides |
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| Authors: | Maria Bocheńska Joanna Kulesza Jarosław Chojnacki Françoise Arnaud-Neu Véronique Hubscher-Bruder |
| Affiliation: | 1. Department of Chemical Technology, Chemical Faculty, Gdansk University of Technology, ul. Narutowicza 11/12, 80-233, Gdansk, Poland 3. Laboratoire de Chimie-Physique, IPHC-DSA, UDS, CNRS, ECPM, 25, rue Becquerel, 67087, Strasbourg Cedex 2, France 2. Department of Inorganic Chemistry, Gdansk University of Technology, ul. Narutowicza 11/12, 80-233, Gdansk, Poland |
| Abstract: | A number of p-tert-butylcalix[4]arene thioamides were synthesized and characterized by 1H-NMR and elemental analysis. Compounds 1–5 are O-substituted derivatives with –CH2–C(=S)–N–X groups, where NX = morpholidyl, NEt2, NHC2H4Ph, NHCH2Ph and NHEt, respectively. The X-ray structures of the ligands 1, 3, 5 and of the complex 3·Pb(ClO4)2, (compound 6), are presented and their slightly distorted cone conformation is established. The influence of the nature of the thioamide functions (secondary or tertiary) on the extractability of some selected metal cations was investigated. Whereas all these calixarenes show the highest extraction level for Ag+, tertiary thioamides are more efficient extractants for Pb2+ than secondary thioamides. |
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