Amphiphilic Amide Derivatives of D-Glucaric Acid. Synthesis and Complexing Properties Toward Lanthanide(III) Ions

Hydrophobic derivatives of D‐glucaric acid, HOOC−(CHOH)4−CONHR,where R is an alkyl chain having 3, 8, 10, or 12 carbon atoms, have been synthesized from D‐glucaro‐1,4‐lactone and the corresponding amines. The complexing abilities of these compounds toward trivalent lanthanide cations have been studi...

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Published inEuropean journal of organic chemistry Vol. 2004; no. 9; pp. 2057 - 2066
Main Authors Aury, Sabrina, Rubini, Patrice, Gérardin, Christine, Selve, Claude
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.05.2004
WILEY‐VCH Verlag
Wiley
Subjects
Amides
Carboxylate ligands
Chemistry
Chemistry, Organic
Lanthanides
NMR spectroscopy
O ligands
Physical Sciences
Science & Technology
amides
CONSTANTS
carboxylate ligands
METAL
NMR spectroscopy
LANTHANUM
lanthanides
O ligands
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Summary:Hydrophobic derivatives of D‐glucaric acid, HOOC−(CHOH)4−CONHR,where R is an alkyl chain having 3, 8, 10, or 12 carbon atoms, have been synthesized from D‐glucaro‐1,4‐lactone and the corresponding amines. The complexing abilities of these compounds toward trivalent lanthanide cations have been studied, using the water‐soluble propyl compound, and compared to that of gulonic acid, which corresponds to the complexing part of these molecules. The formation constants of the complexes have been determined and their structures discussed. The surfactant properties of the C8, C10 and C12 glucaramides and their extracting ability toward LnIII ions have also been evaluated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Bibliography:istex:DB83AE0BF1DB4F6E0C0F5E47E49D1AF20C5F3151
ark:/67375/WNG-5KV66562-M
ArticleID:EJOC200300749
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200300749