Free-radical intermediates and stable products in the oxidation of indole-3-acetic acid

LP Candeias, LK Folkes, MF Dennis…

Index: Candeias, Luis P.; Folkes, Lisa K.; Dennis, Madeleine F.; Patel, Kantilal B.; Everett, Steven A.; et al. Journal of Physical Chemistry, 1994 , vol. 98, # 40 p. 10131 - 10137

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Citation Number: 60

Abstract

The free-radical intermediates and the stable products formed on one-electron oxidation of indole-3-acetic acid (IAA) in aqueous solution were investigated. The dibromine radical anion generated radiolytically reacted with IAA to yield the IAA radical cation. In acid solution, the latter decays by a first-order process (k= 1.8 x lo4 sl) to yield carbon dioxide and the skatole radical. At pH 7 it deprotonates (pKa= 5.09 f 0.02), giving the indolyl radical, ...