Transient Species in the Photolysis of Anils

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Abstract
Two photoinduced isomerizations occur in the photolysis of ethanol solutions of the anil, o‐hydroxybenzylidene‐aniline in the temperature interval 15°—70°C. One isomerization involves the formation of a visible absorption band, λmax 470 mμ, which fades in the dark with a lifetime in the millisecond region. The fading is buffer catalyzed and yields an activation energy of 3.5 kcal/mole for this catalysis. The second isomerization, which is observed as a change in the near ultraviolet spectrum, is about a thousand times more long‐lived and not catalyzed by the presence of buffer, activation energy: 15.0 kcal/mole. The two isomerizations are identified as (1) a hydrogen transfer from the ortho hydroxyl group to the nitrogen atom forming an ortho quinoid structure, (2) a cis—trans isomerization around the C–N double bond.

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