Volume 19, Issue 33
Preparative Organic Chemistry
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ChemInform Abstract: Reactivity Control by Microencapsulation in Simple Ammonium Ion Vesicles.

R. A. MOSS

R. A. MOSS

Dep. Chem., State Univ. N. J., New Brunswick, NJ 08903, USA

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S. SWARUP

S. SWARUP

Dep. Chem., State Univ. N. J., New Brunswick, NJ 08903, USA

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H. ZHANG

H. ZHANG

Dep. Chem., State Univ. N. J., New Brunswick, NJ 08903, USA

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First published: August 16, 1988

Abstract

While normal oxidation of Ellman's anion (I) by iodosobenzoate (II) to Ellman's reagent (III) is quantitatively complete after 2 min and reactions of (I) and (II) occur rapidly on the surface of vesicles of DODAC (IV) (k ca. 0.16-0.24 s-1, only a slow (k ca. 2-7 · 10-3 s-1 permeation-limited oxidation is observed when either (I) or (II) is encapsulated within the DODAC vesicles.

ChemInform Abstract

While normal oxidation of Ellman's anion (I) by iodosobenzoate (II) to Ellman's reagent (III) is quantitatively complete after 2 min and reactions of (I) and (II) occur rapidly on the surface of vesicles of DODAC (IV) (k ca. 0.16-0.24 s-1, only a slow (k ca. 2-7 · 10-3 s-1 permeation-limited oxidation is observed when either (I) or (II) is encapsulated within the DODAC vesicles. Individually encapsulated (I) and (II), however, react with each other only to the extent of ca. 5-10% over 20 h. Similarly, the cleavage of Ellman's reagent (III) to Ellman's anion (I) by dithionite can be controlled by DODAC vesicles, created by sonication (70 W, 15 min) of (IV) in N2-purged pH 8 Tris buffer at 50-55 °C.

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