Intramolecular hydrogen bonding in 1-nitro-5,10-dihydrophenazine derivatives |
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Authors: | I N Borukhova V F Gryazev E G Kovalev Z V Pushkareva |
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Institution: | (1) S. M. Kirov Ural Polytechnic Institute, 620002 Sverdlovsk |
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Abstract: | The formation of free radicals only for derivatives with a nitro group in the 1 position was observed in the oxidation of a number of 5-substituted 5,10-dihydrophenazines with lead dioxide. A long-wave absorption band was observed in the electronic spectra of the derivatives with a nitro group in the 1 position. The assumption of the formation of an intramolecular hydrogen bond in dihydrophenazines with a nitro group in the 1 position was confirmed by quantum-chemical modeling of the three structures of the 1,3-dinitro-5-phenyl-5,10-dihydrophenazine molecule. By comparison of the integral intensities of the bands of the stretching vibrations of the N-H bond in 5-substituted dihydrophenazines it was concluded that this bond is depolarized in derivatives with an intramolecular hydrogen bond.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No, 2, pp, 263–265, February, 1978. |
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