%0 Journal Article
%T Kinetics and Mechanism of Oxidative Conversion of 5-Hydroxyindole to 2-Oxo-5-hydroxyindole by Chloramine-B in Basic Solutions
%J American Journal of Chemistry
%@ 2165-8781
%D 2012
%I 
%R 10.5923/j.chemistry.20120202.03
%X The conversion of 5-hydroxyindole (Indole) to 2-oxo-5-hydroxyindole is an important oxidative transformation in synthetic organic and biochemistry. Under pseudo first-order conditions of[Indole]o >>[chloramine-B or CAB]o, the indole oxidation reaction in a basic solution follows the following experimental rate law: rate = k¡®[CAB]o[Indole]o[OH-]x/[BSA]y, where BSA represents benzenesulfonamide and x and y are fractional orders. The retarding effect of BSA on the rate indicates its involvement in a fast pre-equlibrium in the mechanism of oxidation. Activation parameters have been determined. The variation of[OH-] at constant[BSA] was performed to evaluate the equilibrium and decomposition constants. Based on the mechanism proposed, a rate law has been derived. Furthermore, the methodology developed could be adopted in the synthesis of 2-oxo-5-hydroxyindole. Advantages of the method include: mild reaction conditions, short reaction time, ease of isolation of products, cost effectiveness, and the use of eco friendly reagents.
%K 5 ¨C Hydroxyindole
%K 2 - Oxo - 5 ¨C Hydroxyindole
%K Chloramine ¨C B
%K Benzenesulfonamide
%K Oxidation Kinetics
%K Mechanism
%U http://article.sapub.org/10.5923.j.chemistry.20120202.03.html