Synthesis of new Cu(II)-chelating ligand amphiphiles and their esterolytic properties in cationic micelles

Bhattacharya, Santanu ; Snehalatha, Karnam ; Kumar, V. Praveen (2003) Synthesis of new Cu(II)-chelating ligand amphiphiles and their esterolytic properties in cationic micelles Journal of Organic Chemistry, 68 (7). pp. 2741-2747. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo026323q

Related URL: http://dx.doi.org/10.1021/jo026323q

Abstract

Four new tetradentate 2,6-disubstituted pyridine and tridentate 2-substituted pyridine ligands were synthesized. Two of these compounds possessed a metal ion binding subunit in the form of a 2,6-disubstituted-4-N,N'-dimethylamine pyridine moiety. Cu2+-complexes of these ligands incorporated in cetyltrimethylammonium bromide (CTABr) micelles speeded the cleavage of p-nitrophenyldiphenyl phosphate and p-nitrophenyl hexanoate at pH 7.6. On the basis of a kinetic version of Job plot analysis, a 1:1 ligand/Cu2+ stoichiometry was found to be the most active species. In CTABr micelles, the pKa values for the Cu2+-coordinated hydroxyl or pendant -CH2OH in these ligands were between 7.8 and 7.9. The metallomicellar systems displayed catalytic (turnover) behavior in the presence of excess substrates.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:20884
Deposited On:20 Nov 2010 13:24
Last Modified:20 Nov 2010 13:24

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