Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent, Safety of 5,6-Dihydroxyindole, Which mentioned a new discovery about 3131-52-0
The one-electron oxidation of a series of hydroxylated and methoxylated indoles by the azide radical in aqueous solution at pH 5-9 (k ca. (4-9) x 109 dm3 mol-1 s-1) has been studied with the use of the technique of pulse radiolysis with spectrophotometric detection.One-electron oxidation of 5,6-dihydroxyindole (DHI) and its N-methyl-substituted analogue (MeDHI) results in the formation of the corresponding indole semiquinone radical with pKa value of 6.8 +/- 0.2.Methylation of one of the hydroxy groups of DHI (or MeDHI) results in formation of the correspondin g indoloxyl radical.In contrast, methylation of both hydroxy groups of DHI yields 5.6-dimethoxyindole (DMI), which, upon one-electron oxidation, forms the indolyl radical with a pKa of 6.0 +/- 0.2.Further methylation at N(1) of DMI causes the radical cation to be stabilized over the pH range studied.From a comparison of the spectral characteristics of these radicals, the preferred site of deprotonation of the radical cation of DHI is identified to be from the 6-hydroxy group.With the exception of DHI (or MeDHI), the radicals produced decay bimolecularly in the dose/pulse range of 1-18 Gy used in these studies.It is concluded that the types of radical produced upon one-electron oxidation of methoxylated and hydroxylated indoles are critically dependent upon the sites of methylation of these indoles.
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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles