A series of newly synthesized nine aroyl/heteroacyl-1,4-benzoquinones (RCO-BQ) undergoes one-electron reduction in pulse radiolytic reducing conditions in an aqueous- 2-propanol-acetone mixed solvent (MS). The radical centre is mainly located in the quinone ring, though a small probability exists for reduction at the carbonyl (CO) group. The intramolecular hydrogen bonding between the OH group of the semiquinone ring and the adjacent CO group makes the radical more stable as compared to the simple benzosemiquinone radical. A red-shifted absorption band arises mainly due to large conjugation in the semiquinone. The substitutions (R), thiophenyl, phenyl and furanyl groups at the keto position reduce their one-electron reduction potential (E1) values from -30 mV for BQ to <-300 mV in some of these quinones.
Research on Chemical Intermediates – Springer Journals
Published: Jul 1, 2001
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