Photochemical Reduction of Nitrobenzene and Its Reduction Intermediates. IX. The Photochemical Reduction of 4-Nitropyridine in a Hydrochloric Acid-Isopropyl Alcohol Solution

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概要

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• The photochemical reduction of 4-nitropyridine has been investigated in hydrochloric acid-isopropyl alcohol solutions. 4-Nitropyridine was not photoreduced in isopropyl alcohol, whereas when the photolysis was carried out in hydrochloric acid-isopropyl alcohol solutions, the photoreduction of 4-nitropyridine proceeded from its <I>n</I>,π<SUP>*</SUP> triplet state to give 4-hydroxylaminopyridine in a quantitative yield. The quantum yields for the disappearance of 4-nitropyridine in hydrochloric acid-isopropyl alcohol solutions increased with the concentration of hydrochloric acid up to 3.6×10<SUP>−2</SUP> mol <I>l</I><SUP>−1</SUP> (Φ=0.27–0.94). These results suggest that the hydrogen abstraction of photoexcited 4-nitropyridine proceeds electrophilically because of the decrease in the electron density of the nitro group, in decrease resulting from the protonation of heterocyclic nitrogen and the <I>n</I>,π<SUP>*</SUP> excitation of the nitro group.

• 公益社団法人 日本化学会の論文

著者

• Kano Koji

  Department Of Molecular Science And Technology Doshisha University

• Ueda Kazuo

  Department Of Acoustic Design Kyushu Institute Of Design

• Hashimoto Shizunobu

  Department of Applied Chemistry, Doshisha University

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