Evidence for the formation of acylated or phosphorylated monoperoxyphthalates in the catalytic esterolytic reactions in cationic surfactant aggregates

Bhattacharya, S and Snehalatha, K (1997) Evidence for the formation of acylated or phosphorylated monoperoxyphthalates in the catalytic esterolytic reactions in cationic surfactant aggregates. In: Journal Of Organic Chemistry, 62 (7). pp. 2198-2204.

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Abstract

Monoperoxyphthalate (MPP) was solubilized in three different aqueous cationic surfactant aggregates composed of(i) a micellar cetyltrimethylammonium chloride (CTACl) solution; (ii) an oil-in-water (O/W) microemulsion (ME) stabilized by CTACl, and a cosurfactant, tert-butyl alcohol, and (iii) a vesicular medium composed of dispersions of dihexadecyldimethylammonium chloride (DHDAC). At pH similar to 8.5 and 25 degrees C, each of these formulations was used eo cleave p-nitrophenyl diphenyl phosphate (PNPDPP). The aggregate and the maximum pseudo-first-order rate constants ([MPP] = 4 x 10(-5) M, and [PNPDPP] = 1 x 10(-5) M) for the PNPDPP cleavages are the following: buffer alone, 0.00034 s(-1); micelle: 0.024 s(-1); ME: 0.0048 s(-1); and vesicle: 0.025 s(-1) Importantly all the catalytic formulations showed ''turnover'' behavior in the presence of excess substrates. By the combined use of H-1- and P-31-NMR spectrometry and synthesis, it was possible to provide evidence for the formation of acylated or phosphorylated monoperoxypthalates in the catalytic hydrolyses in cationic surfactant aggregates.

Item Type:	Journal Article
Publication:	Journal Of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	Copyright of this article belongs to American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	17 Jul 2009 10:30
Last Modified:	19 Sep 2010 05:26
URI:	http://eprints.iisc.ac.in/id/eprint/18955

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