Hydrogen-bonding Effects on the Electron Spin Resonance Spectra of the Anion Radicals of Several Aromatic Amine <I>N</I>-Oxides

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概要

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• The hydrogen-bonding effects of ethanol, phenol, and water on the electron-spin-resonance spectra of the anion radicals of 4-nitro- and 4-cyano-pyridine <I>N</I>-oxides, pyrazine mono- and di-<I>N</I>-oxides, and 4-nitropyridine electrochemically generated in dimethylformamide have been studied quantitatively. The equilibrium constant, <I>K</I>, pertinent to the hydrogen-bonding systems was determined on the basis of analyses of the variation in the hyperfine coupling constant caused by the addition of a proton donor. The active site in a radical anion participating in the hydrogenbonding interaction and the <I>K</I> values were then discussed on the basis of the theoretical calculation of the spin density and the coupling constant of the radicals in the hydrogen-bonding interaction. It has been pointed out that this sort of experiment in hydrogen bonding interaction is also useful for assigning the hyperfine coupling constant to a definite atom in a radical. Last, these <I>K</I> values are used to explain the mechanism of radical formation by the controlled potential electrolysis at different reduction potentials of pyrazine mono- and di-<I>N</I>-oxides in dimethylformamide-ethanol mixed solvents.

• 公益社団法人 日本化学会の論文

著者

• Kubota Tanekazu

  Shionogi Research Laboratory Shionogi & Co., Ltd.

• Miyazaki Hiroshi

  Shionogi Research Laboratories, Shionogi and Co., Ltd.

• Miyazaki Hiroshi

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• Oishi Yoshiko

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• Nishikida Koichi

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

• Oishi Yoshiko

  Shionogi Research Laboratory, Shionogi & Co., Ltd.

関連論文

• Polarography of Pyridine N-Oxide and its Alkyl Derivatives
• Charge-transfer model in considering the reactivity of heteroaromatic nitriles with the enolate anion.
• The Singlet-Triplet Absorption Spectra of Heterocyclic Amine iV-Oxides. II. Pyridine N-Oxide Derivatives
• The Relation between the Electronic Spectra and the Oxidation and Reduction Potentials of Benzenoid Hydrocarbons
• The Singlet-triplet Absorption Spectra of Heterocyclic Amine N-Oxides (I)
• Hydrogen-bonding Effects on the Electron Spin Resonance Spectra of the Anion Radicals of Several Aromatic Amine N-Oxides
• The Effects of Ion-pair Formation on the ESR Spectra of the Anion Radicals of 4-Nitropyridine N-Oxide and 4-Nitropyridine
• Cyclic voltammetry of aromatic amine N-oxides in nonaqueous solvents and the stability of the free radicals produced.
• The electronic spectra and nonaqueous oxidation and reduction potentials of azoxybenzenes, and their mutual correlation.

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