One-electron reduction studies on some aroyl/heteroacyl-1,4-benzoquinones (RCO-BQ)

One-electron reduction studies on some aroyl/heteroacyl-1,4-benzoquinones (RCO-BQ) 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. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

One-electron reduction studies on some aroyl/heteroacyl-1,4-benzoquinones (RCO-BQ)

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Publisher
Springer Journals
Copyright
Copyright © 2001 by VSP
Subject
Chemistry; Inorganic Chemistry; Physical Chemistry; Catalysis
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1163/156856701104202246
Publisher site
See Article on Publisher Site

Abstract

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.

Journal

Research on Chemical IntermediatesSpringer Journals

Published: Jul 1, 2001

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