Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Photochemistry of Acetanilide. IV. The Photochemical Reactions in the Vapor Phase and Rigid Matrixes
Haruo ShizukaIkuzo Tanaka
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1969 Volume 42 Issue 4 Pages 909-913

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Abstract

The photolysis of acetanilide in the vapor phase at 2537 Å and 120°C has been studied by means of mass spectrometry, gas chromatography, and spectrophotometry. In the vapor phase, no such rearrangements of acetanilide as in the liquid phase occurred, only the decomposition of acetanilide. Carbon monoxide and ethane were formed as the main products, and the ratio of carbon monoxide to ethane was about 2. The quantum yield of the predissociation for the N–C bond of acetanilide in the vapor phase was estimated to be 0.28 from the data of the quantum yields for the formations of carbon monoxide and ethane. A small amount of methane and traces of hydrogen and benzene were also detected. The reaction scheme of acetanilide in the vapor phase at 2537 Å and 120°C has been proposed. On the other hand, the photochemical reactions of acetanilide in the rigid matrixes (MP, ME, and EPA) at −196°C and in the PVA sheet at room temperature have also been carried out by the use of a spectrophotometer and an ESR spectrometer. In the rigid matrixes at −196°C, the photochemical rearrangements did not occur, only the back reaction resulting in the distortional structure of acetanilide; this mechanism can be explained by the stiffness of the solvent cage. The cage effect on the photochemical reaction of acetanilide is also discussed.

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