Evidence of Enhanced Reactivity of DAAP Nucleophiles toward Dephosphorylation and Deacylation Reactions in Cationic Gemini Micellar Media

4,4‘-(Dialkylamino)pyridine (DAAP)-based compounds 1−4 catalytically cleave hydrophobic organophosphate and carboxylate esters in various host micellar aggregates at mildly alkaline pH. The role of the micellar reaction medium in such esterolytic reactions has been carefully examined in this work. T...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-01, Vol.69 (2), p.559-562
Main Authors: Bhattacharya, Santanu, Kumar, V. Praveen
Format: Article
Language:English
Subjects:
Chemical reactivity
Chemistry
Exact sciences and technology
Organic chemistry
Reactivity and mechanisms
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Summary:4,4‘-(Dialkylamino)pyridine (DAAP)-based compounds 1−4 catalytically cleave hydrophobic organophosphate and carboxylate esters in various host micellar aggregates at mildly alkaline pH. The role of the micellar reaction medium in such esterolytic reactions has been carefully examined in this work. The cationic gemini surfactant based micellar aggregates provide more than 1 order of magnitude better reaction medium for the above reactions than their conventional single-chain, single-charge, cationic cetyl trimethylammonium bromide (CTABr) micelles. The catalytic turnover behavior of DAAP nucleophiles in the presence of excess substrates is also retained in gemini micellar media.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034745+