Journal
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
Volume 23, Issue 6, Pages 536-543Publisher
WILEY
DOI: 10.1002/poc.1637
Keywords
chalcogen-nitrogen pi-heterocycles; cyclic voltammetry; DFT calculations; electrochemical oxidation; electrochemical reduction; EPR spectroscopy; fluorinated pi-heterocycles; radical anions
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Funding
- Presidium of the Russian Academy of Sciences [18.17]
- Siberian Branch of the Russian Academy of Sciences [105]
- Russian Foundation for Basic Research [07-03-00467]
- Russian Federal Agency of Education [NK-386P(3)]
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In comparison with 2,1,3-benzothia(selena)diazoles, electrochemical oxidation and reduction of their 4,5,6,7-tetrafluoro derivatives and a number of related compounds were studied by cyclic voltammetry. For nine examples of this class, the first reduction peaks are reversible and corresponding radical anions (RAs) are long-lived at 295 K in MeCN and especially in DMF. The oxidation peaks were irreversible and corresponding radical cations were not observed. Electrochemically generated RAs were characterized by EPR measurements and DFT calculations at the UB3LYP/6-31+G(d) level. The spin density distribution in the RAs is analyzed in connection with effects of S substitution by Se and/or H by F. The prospects of the studied RAs in the design and synthesis of magnetically active materials are discussed. Copyright (C) 2010 John Wiley & Sons, Ltd.
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