Add time:08/11/2019         Source:sciencedirect.com

UV, gamma-, or X-irradiation of several N-hydroxyxanthines as powdered solids produces radicals that are indefinitely stable in the solid state at room temperature, but are highly unstable in protic solvents. The ESR spectra are not sufficiently resolved to be definitive but are compatible with an amidogen radical, the unpaired electron of which is partially delocalized through the aromatic π system. Structural characterization was obtained by comparing the UV induced radicals from 3-hydroxyxanthine and 3-hydroxy-8-methylxanthine with chemically generated nitroxyl radicals from the same compounds. These two radical species show differences in their ESR spectra, in the extent of interaction of the unpaired electron with the methyl group at position 8, and in the products resulting upon reaction in water.The amidogen radical reacts instantaneously with water to yield the parent xanthines. Parallels are drawn between this reduction of the amidogen radical, the photoreduction of 3-hydroxyxanthine when solutions of it are irradiated with UV light, and the reduction of 3-acetoxyxanthine in aqueous solution in the absence of light.The synthesis of a requisite derivative, 3-hydroxy-7,8-dimethylxanthine, is reported.

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