The radical anion of anthraquinone (AQ•−) has been generated by the reduction of anthraquinone (AQ) with sugars in aqueous alkaline solution. This appears to be the first time that the radical has been observed (esr spectrometry) in an entirely aqueous medium. Alkaline methanol solutions of AQ, when irradiated with light, yielded colourless solutions also exhibiting strong esr signals characteristic of. AQ•−.The ability of various carbohydrate and lignin preparations to reduce AQ, or to oxidize the reduced forms of AQ, was also investigated, both by direct observation and by electrode potential measurements. In very concentrated alkali, AQ was reduced by glucose to a green solid thought to be a quinhydrone.
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