Journal
JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY
Volume 61, Issue 3-4, Pages 381-391Publisher
SPRINGER
DOI: 10.1007/s10847-008-9434-4
Keywords
amino acids; association constants; calix[4]arenes; molecular recognition in water; phosphonic acids; supramolecular chemistry; complex formation
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Series of the calix[4]arene phosphonic acids with various substituents at the lower rim was synthesized. Complexing properties of these receptors towards methyl esters of six amino acids strongly depended on the calix[4]arene conformation flexibility. The complex formation processes were monitored using H-1 NMR spectroscopy (deuterated phosphate buffer at pD 7.3, 22 degrees C) and association constant values were evaluated. Inherently mobile calix[4]arene molecule 3 occurred in cone conformation in aqueous solution turned out to be more effective in complexation of the basic amino acids methyl esters compared to the rigid 2 and flexible 4. Mixed 1:2 and 2:1 (host-guest) complexes were observed for compound 1 with all amino acids methyl esters.
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