Anodic oxidation of selenadiazoloquinolones in alkaline media

作者：Stasko Andrej; Zalibera Michal; Barbierikova Zuzana; Rimarcik Jan; Lukes Vladimir; Bella Maros; Milata Viktor; Brezova Vlasta^*

来源：Magnetic Resonance in Chemistry, 2011, 49(4): 168-174.

DOI：10.1002/mrc.2716

• 6-oxo-6,9-dihydro[1,2,5]selenadiazolo[3,4-h]quinoline
• anodic oxidation
• EPR spectroscopy
• UV/Vis spectroscopy
• ortho semiquinone
• DFT calculations

Newly synthesized derivatives of 6-oxo-6,9-dihydro[1,2,5] selenadiazolo[3,4-h] quinoline variously substituted at position 7 (R = H, COOH, COCH3, CN, COOC2H5 and COOCH3) are established in strongly alkaline aqueous solutions (0.1 M NaOH; pH similar to 13) as N(9)-deprotonated structures, but in less alkaline solutions (0.001 M NaOH; pH similar to 11) the N(9)-protonated oxo tautomeric forms dominate. Upon their anodic oxidation in alkaline solutions, the selenadiazole ring is replaced, forming instead the paramagnetic species analogous to the ortho semiquinone radical anions as monitored by in situ EPR spectroscopy. The quantum chemical calculations for two representative selenadiazoloquinolones (R = H and COOH) and their anodic oxidation products presented are in agreement with experiments.

• 出版日期2011-4