Lower rim substituted p-tert-butyl calix[4]arene; Part 14. Synthesis, structures and binding studies of calix[4]arene thioamides

A number of p-tert -butylcalix[4]arene thioamides were synthesized and characterized by 1 H-NMR and elemental analysis. Compounds 1 – 5 are O -substituted derivatives with –CH 2 –C(=S)–N–X groups, where NX = morpholidyl, NEt 2 , NHC 2 H 4 Ph, NHCH 2 Ph and NHEt, respectively. The X-ray structures of...

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Published in:Journal of Inclusion Phenomena and Macrocyclic Chemistry 2010-10, Vol.68 (1-2), p.75-83
Main Authors: Bocheńska, Maria, Kulesza, Joanna, Chojnacki, Jarosław, Arnaud-Neu, Françoise, Hubscher-Bruder, Véronique
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Crystallography and Scattering Methods
Food Science
Organic Chemistry
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Summary:A number of p-tert -butylcalix[4]arene thioamides were synthesized and characterized by 1 H-NMR and elemental analysis. Compounds 1 – 5 are O -substituted derivatives with –CH 2 –C(=S)–N–X groups, where NX = morpholidyl, NEt 2 , NHC 2 H 4 Ph, NHCH 2 Ph and NHEt, respectively. The X-ray structures of the ligands 1 , 3 , 5 and of the complex 3 ·Pb(ClO 4 ) 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 Pb 2+ than secondary thioamides.
ISSN:0923-0750
1573-1111
DOI:10.1007/s10847-010-9735-2