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In the nitration of 3-acyl- and 3-carbethoxyindoles with various nitrating agents, the ratio of substitution of the hydrogen atoms in the 4 or 6 positions or the replacement of the acyl group in the 3 position by a nitro group depend on the conditions. Replacement of the carbethoxy group in the 3 position is not observed. The experimental data were compared with the reactivity indexes calculated by the LCAO MO method. It was concluded that replacement of the hydrogen atoms in the benzene ring of the investigated models proceeds as electrophilic attack of an unprotonated molecule of the indole compound.
KeywordsNitrate Benzene Organic Chemistry Hydrogen Atom Indole
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