Abstract
The synthesis and crystal structure of p-tert-butylthia- and p-tert-butylcalix[4]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 thiacalix[4]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.
Original language | English |
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Pages (from-to) | 239-250 |
Number of pages | 12 |
Journal | Journal of Inclusion Phenomena and Macrocyclic Chemistry |
Volume | 62 |
Issue number | 3-4 |
DOIs | |
Publication status | Published - 2008 Dec |
Keywords
- Conformation
- Diethylthiophosphate ester
- Metal complexation
- Thiacalixarenes
- X-ray structures
ASJC Scopus subject areas
- Food Science
- Chemistry(all)
- Condensed Matter Physics