Model studies toward trivalent cation binding by appropriately functionalized calix[4]arenes

Molecular modeling and molecular dynamics of a series of calix[4]arene tetracarboxylic acids and tricarboxylic acid monoamides revealed that in an aqueous environment the phenolic oxygen atoms do not participate in the complexation of Ac3+. This observation led to the design and synthesis of new cal...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 2 no. 11; pp. 2351 - 2360
Main Authors Grote Gansey, MHB, Verboom, W, van Veggel, FCJM, Vetrogon, Arnaud-Neu, F, Schwing-Weill, MJ, Reinhoudt, DN
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.11.1998
Subjects
Chemistry
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
MONTE-CARLO
MOLECULAR-DYNAMICS
EU3
CONE CONFORMATION
LANTHANIDE IONS
COMPLEXES
FORCE-FIELD
FREE-ENERGY
AQUEOUS-SOLUTION
WATER
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Summary:Molecular modeling and molecular dynamics of a series of calix[4]arene tetracarboxylic acids and tricarboxylic acid monoamides revealed that in an aqueous environment the phenolic oxygen atoms do not participate in the complexation of Ac3+. This observation led to the design and synthesis of new calix[4]arene based ionophores, containing multiple glycine units, having an increased number of potential donor sites. Potentiometric titrations in methanol with La3+ as a non-radioactive model for Ac3+ indicated that, although the level of complexation is high for all ligands, a new calix[4]arene derivative 5 is superior at pH < 4.
ISSN:1472-779X
0300-9580
1364-5471
DOI:10.1039/a805950k