The electrochemical behaviors of l‐hydroxy‐9,10‐anthraquinone (HOAQ) and its conjugate base false(OAQ−false) have been compared in DMF and acetonitrile solvents, HOAQ is reduced in two one‐electron steps to stable anion radical and dianion, while OAQ− reduces in a single two‐electron wave accompanied by a monoprotonation reaction. Addition of phenol as proton source to DMF solutions of OAQ− forms a heteroconjugate acid‐base dimer, ØOH…OAQ− . This complex is reduced at a potential intermediate between that of HOAQ and OAQ− , and interpretation of its reaction includes consideration of concomitant formation of ØOH…OØ− homoconjugate dimer. The conjugate base OAQ− is oxidizable by a one‐electron reaction which is followed by rapid hydrogen atom abstraction to yield HOAQ as product. Combined thin‐ layer spectroelectrochemical and coulometric measurements form an important supplement to the conventional electroanalytical methods used in this study.

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