One-Electron Oxidation of Indoles and Acid-Base Properties of the Indolyl Radicals

Article abstract of DOI:10.1021/j100300a039

The rates of attack of OH^. N3^., Br2^.-, CO3^.-, and ClO2^. on indole and four methylated indoles have been determined.All primary oxidants except for OH^. were found to form indolyl radicals quantitatively.The OH^. radical produces 44percent indolyl radicals with indole. 3-Methylation affects this yield only slightly while 2- or N-methylation increase the yield of indolyl radicals above 60percent.The acid-base properties of the indolyl radicals have also been explored.Finally the one-electron reduction potential of the radical cation of indole has been determined to be 1.24 +/- 0.01 V.