Abstract
The polarographic behavior of 5H-benzo[a]phenothiazin-5-one and its ring-substituted derivatives at a dropping mercury electrode was studied in N,N-dimethylformamide (DMF). Each compound gave well-defined two reduction waves, the half-wave potentials of which linearly correlated with theHammett substituent constant σ p . For the parent compound, 5H-benzo[a]phenothiazin-5-one, the polarographic behavior was also investigated in selected other solvents. From the similarity with the behavior of anthraquinone, the results obtained in a mixed solvent,DMF—methylcellosolve, were explained by assuming a disproportionation reaction between the parent compound and its dianion.
Zusammenfassung
Es wurde das polarographische Verhalten von 5H-Benzo[a]phenothiazin-5-on und dessen ringsubstituierten Derivaten an der tropfenden Quecksilberelektrode in N,N-Dimethylformamid (DMF) untersucht. Alle Verbindungen gaben zwei wohldefinierte Reduktionswellen, deren Halbwellenpotentiale mit denHammett'schen Substituentenkonstanten σ p eine gute lineare Korrelation ergaben. Bezüglich der Stammsubstanz, 5H-Benzo[a]phenothiazin-5-on, wurde das polarographische Verhalten auch in einigen anderen Lösungsmitteln untersucht. Aus Parallelen mit dem Verhalten von Anthrachinon wurden die Ergebnisse, die inDMF—Methylcellosolv als gemischtem Lösungsmittel erhalten wurden, unter der Annahme einer Disproportionierungs-Reaktion zwischen der Stammverbindung und dessen Dianion erklärt.
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Ueno, Y. The polarographic reduction of 5H-benzo[a]phenothiazin-5-ones in non-aqueous media. Monatsh Chem 117, 327–333 (1986). https://doi.org/10.1007/BF00816526
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DOI: https://doi.org/10.1007/BF00816526