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Modification of calix[4]arenes with CMPO-functions at the wide rim. Synthesis, solution behavior, and separation of actinides from lanthanides.
MedLine Citation:
PMID:  14664399     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
Two calix[4]arene tetraethers (Y = C5H11, C14H29) bearing on their wide rim four -N(Me)-CO-CH2-P(O)Ph2 residues were synthesized for the first time. Their ability to extract lanthanides and actinides from an acidic aqueous phase to organic phases (CH2Cl2, NPHE) was studied. In comparison to the corresponding -NH-analogs, they are less efficient extractants, the selectivity for the light over the heavy lanthanides is less pronounced, while there is still an interesting selectivity of Am3+ over Eu3+. Stability constants for selected lanthanide salts were determined also in homogenous phase (methanol, acetonitrile) but do not account for the different extraction results. The complexation of Gd3+ was also followed by relaxivity (NM RD) measurements, which suggest an even stronger aggregation for the N-methyl compound while the 1:1 complex is reached for a smaller ratio [L]/[Gd3+] compared to the NH analog. The formation of aggregates is also supported by dynamic light scattering measurements. A single crystal X-ray structure of the pentyl ether reveals a C2-symmetrical pinched cone conformation for the free ligand.
Authors:
Christian Schmidt; Mohamed Saadioui; Volker Böhmer; Valéry Host; Marie-Rose Spirlet; Jean F Desreux; Fréderic Brisach; Françoise Arnaud-Neu; Jean-François Dozol
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  1     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2003 Nov 
Date Detail:
Created Date:  2003-12-10     Completed Date:  2004-10-08     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  4089-96     Citation Subset:  -    
Affiliation:
Fachbereich Chemie und Pharmazie, Abteilung Lehramt Chemie, Johannes Gutenberg-Universität, Duesbergweg 10-14, D-55099 Mainz, Germany.
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