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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

  • Maria BocheńskaEmail author
  • Joanna Kulesza
  • Jarosław Chojnacki
  • Françoise Arnaud-Neu
  • Véronique Hubscher-Bruder
Original Article

Abstract

A number of p-tert-butylcalix[4]arene thioamides were synthesized and characterized by 1H-NMR and elemental analysis. Compounds 15 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.

Keywords

p-tert-butylcalix[4]arene thioamides Synthesis Crystal structure Liquid–liquid extraction 

Notes

Acknowledgement

Financial support from the Polish Ministry of Higher Education and Science, grant No N204 274235, is gratefully acknowledged.

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Copyright information

© Springer Science+Business Media B.V. 2010

Authors and Affiliations

  • Maria Bocheńska
    • 1
    Email author
  • Joanna Kulesza
    • 1
    • 3
  • Jarosław Chojnacki
    • 2
  • Françoise Arnaud-Neu
    • 3
  • Véronique Hubscher-Bruder
    • 3
  1. 1.Department of Chemical Technology, Chemical FacultyGdansk University of TechnologyGdanskPoland
  2. 2.Department of Inorganic ChemistryGdansk University of TechnologyGdanskPoland
  3. 3.Laboratoire de Chimie-PhysiqueIPHC-DSA, UDS, CNRS, ECPMStrasbourg Cedex 2France

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