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Licensed Unlicensed Requires Authentication Published by De Gruyter April 2, 2013

Alkyl Triphenylphosphonium Bromide Surfactant Mediated Reactions of p-Nitrophenyl Acetate

Mediatisierte Reaktionen von p-Nitrophenylacetat mittels Alkyltriphenylphosphoniumbromid-Tensid
  • S. Moore , R. M. Palepu , S. Bal , K. K. Ghosh and P. R. Dafonte

Abstract

Kinetic measurements were performed for the hydrolysis of p-nitrophenyl acetate as a model compound in micellar media. This reaction was studied both in the presence and absence of various α-effect nucleophiles, and in depth analyses were performed using acetohydroxamic acid (AHA). Rate surfactant profiles were obtained in the absence and presence of the AHA nucleophile for the alkyl triphenylphosphonium bromides (CnPPh3Br) surfactant series. All rate surfactant profiles were analyzed using the pseudophase model and modified pseudophase model (In the presence of nucleophile) in order to obtain the regression parameters, including binding constants and rate constants in the micellar pseudophase. Studies in the presence of acetohydroxamic acid and the alkyl triphenylphosphonium surfactants were also conducted as a function of pH to obtain the pKa value of the acetohydroxamic acid in the micellar media.

Kurzfassung

Für die Hydrolyse von p-Nitrophenylacetat als Modellverbindung wurden Kinetikmessungen in mizellaren Medien ausgeführt. Diese Reaktion wurde sowohl in Anwesenheit als auch in Abwesenheit verschiedener α-Effektnukleophile und in eingehenden Analysen mittels Acetohydroxamsäure (AHA) ausgeführt. Für die Tensidreihe der Alkyltriphenylphosphoniumbromide (CnPPh3Br) wurden Tensidgeschwindigkeitsprofile in An- und Abwesenheit von AHA-Nukleophilen erhalten. Um die Regressionsparameter, einschließlich Bindungs- und Geschwindigkeitskonstanten in der mizellaren Pseudophase zu erlangen, wurden alle Tensidgeschwindigkeitsprofile mittels Pseudophasenmodel und modifiziertem Pseudophasenmodel (in Gegenwart von Nukleophilen) analysiert. Untersuchungen in Gegenwart von Acetohydroxamsäure und Alkyltriphenylphosphoniumbromid-Tensiden wurden außerdem als eine Funktion des pHs ausgeführt, um die pKa-Werte von Acetohydroxamsäure in mizellaren Medien zu erhalten.


Kallol K. Ghosh, School of Studies in Chemistry, Pt. Ravishankar Shukla University, Raipur 492010, India. E-mail:

Dr. Kallol K. Ghosh is presently a reader of physical chemistry at Pt. Ravishanker Shukla University, Raipur, India. Since 1998. He had been INSA/JSPS fellow at Seikei University, Tokyo, Japan and James Chair visiting fellow at St. Francis Xavier University, Antigonish, Canada. He has published 80 research papers. His research is focused on micellar catalysis, reaction mechanism, hydroxamic acids and detoxification.

Ms Sunita Bal is a Ph.D student of School of Studies in Chemistry, Pt. Ravishanker Shukla University, Raipur, India.

Dr. R. Palepu is a professor of Chemistry at St. Francis Xavier University, Antigonish, Nova Scotia, Canada, for the past ten years and prior to his appointment at this university he taught at University College of Cape Breton, Sydney Nova Scotia for 23 years. Dr. Palepu's research interests lie in the general area of Colloidal Chemistry and carried out his research with undergraduate students. To this date Dr. Palepu had published 149 papers in various international journals. This is his last academic term and he will be retiring as a professor of Chemistry at the end of August 2007.

Miss Sarah Moore graduated with 1st class Honours degree in Chemistry from St. Francis Xavier University and currently enrolled in the Doctoral studies in Medicine at University of Toronto, Canada.

Dr Pedro Rodriguez Dafonte is a physical chemist and obtained PhD degree from University of Vigo in 2001. From 2001–2003 he worked as assistant professor at the University of Ourense. He then spent a year as a post doctoral fellow in the group of Prof Terrier at the University of Versailles(France). Since 2004 he has been working as a researchers at the University de Santiago de Compostela under a research program of Xunta de Galicia (IPP).


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Received: 2007-01-12
Published Online: 2013-04-02
Published in Print: 2007-06-01

© 2007, Carl Hanser Publisher, Munich

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