Functionalized surfactant mediated reactions of carboxylate, phosphate and sulphonate esters

Nucleophilic reactivity of some functionalized surfactants, i.e. quaternary pyridinium aldoximes towards the hydrolysis of p‐nitrophenyl acetate (PNPA), p‐nitrophenyl benzoate (PNPB), p‐nitrophenyldiphenyl phosphate (PNPDPP) and p‐nitrophenyl p‐toluene sulphonate (PNPTS) has been studied at pH 7.1 a...

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Bibliographic Details
Published in:Journal of physical organic chemistry 2010-06, Vol.23 (6), p.519-525
Main Authors: Tiwari, Shuchi, Ghosh, Kallol K., Marek, Jan, Kuca, Kamil
Format: Article
Language:English
Subjects:
Benzoates
Esters
functionalized surfactants
Hydrolysis
kinetics
micelles
pyridinium aldoximes
Spectrophotometry
Surfactants
Toluene
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Summary:Nucleophilic reactivity of some functionalized surfactants, i.e. quaternary pyridinium aldoximes towards the hydrolysis of p‐nitrophenyl acetate (PNPA), p‐nitrophenyl benzoate (PNPB), p‐nitrophenyldiphenyl phosphate (PNPDPP) and p‐nitrophenyl p‐toluene sulphonate (PNPTS) has been studied at pH 7.1 and 27 °C. Addition of functionalized surfactant to reaction medium causes progressive increase in the rate of hydrolysis and reaches a maximum and then decreases due to further addition of surfactant. An increase in the alkyl chain length of functionalized surfactants resulted in an increase in the first‐order rate constant. The apparent pKa and CMC of functionalized surfactants have also been determined by spectrophotometric and conductometric methods, respectively. Copyright © 2009 John Wiley & Sons, Ltd. Nucleophilic reactivity of some functionalized surfactants i.e., quaternary pyridinium aldoximes towards the hydrolysis of different esters PNPA, PNPB, PNPDPP and PNPTS has been studied at pH 7.1 and 27°C. Series (1A) and (1B) are effective functionalized surfactants and can be used as a novel micellar catalyst under mild conditions.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.1635