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A series of indolequinones bearing substituted nitrophenols on the (indol-3-yl)methyl position was synthesised. The nitrophenol leaving groups were appropriately substituted to give a wide range (4 units) in phenolic pK a value. The rate of reductive elimination of phenoxide anions from the (indol-3-yl)methyl position of semiquinone radicals was dependent upon this pK a , with a decrease in 3.8 pK units shortening the half-life from 28 to 1.5 ms. Only 2,4dinitrophenol (pK a = 3.9) wasdoi:10.1039/b101842f fatcat:23x3s3m4yfcohb2bbbyxo25qeq