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A series of o-quinoid compounds are generated by photolysis of phenylwbene and phenylnitrene precursors bearing appropriate functional groups at the ortho position in an argon matrix at 10 K and are analyzed by IR and UV/vis spectra. Attempts to convert these quinoid compounds to their valence isomers show that photointerconvertibility is possible only with the quinone methide system. Experimental IR spectra of the observed products are shown to match quite well with the theoretical frequencies calculated by ab initw method. Optimized geometries and energies of the quinoid compounds and their valence isomers are also calculated and are employed to interprete the observed dependence of the reversibility between the isomers on the structure.

Matrix isolation study of reactive o-quinoid compounds: Generation detection and reactions