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- W2080283236 abstract "The e.s.r. spectra generated in methyl α-D-glucopyranoside (1) and some selected derivatives thereof by high-energy radiation have been examined to determine the nature of the radiation damage. Evaluations of the e.s.r. spectra of irradiated methyl tetra-O-acetyl-α-D-glucopyranoside (2), methyl tetra-O-[(p-ethoxycarbonyl)benzoyl]-α-D-glucopyranoside (3), methyl tetra-O-(p-methoxybenzoyl)-α-D-glucopyranoside (4), methyl tetra-O-(p-nitrobenzoyl)-α-D-glucopyranoside (5), methyl tetra-O-(ochlorobenzoyl)-α-D-glucopyranoside (6), methyl tetra-O-p-tolylsulfonyl-β-D-glucopyranoside (7), methyl tetra-O-nicotinoyl-α-D-glucopyranoside (8), and methyl tetra-O-(phenylcarbamoyl)-α-D-glucopyranoside (9) contained mainly one type of stable free-radical, together with some secondary radical in low concentration. The e.s.r. spectrum of compound 1 consisted of one doublet and one singlet; this observation was explained by assuming that the free electron position is at C-1, so that the cleavage of the C-1O glycosidic bond would give rise to the doublet, and the dehydrogenation of the C-1H bond would give rise to the singlet. For most of the substituted D-glucopyranosides studied, irradiation gave singlet spectra which were explained by assuming the radical site to be C-1 (by the dehydrogenation of the C-1H bond). The aromatic groups present in the substituted D-glucopyranosides were known to protect the glycosides from radiation damage1. In the aromatically substituted D-glucopyranosides, no reducing power was measurable, even when the compounds were irradiated to dosages as high as 5.2 x 1021 eV/g; this was additional evidence that no cleavage of the C-1O glycosidic bond occurs during irradiation of these compounds. The absence of hyperfine splitting of the free electron at C-1 with H-2 was explained by a change in the conformation of the molecule after H-1 had been cleaved. Displacement of the hydrogen atoms would then occur to remove any deformation of the ring caused thereby; this would remove H-2 from the vicinity of the unpaired electron at C-1. No thermally induced free-radicals could be detected in these compounds, unless they were heated to charring." @default.
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- W2080283236 date "1968-03-01" @default.
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- W2080283236 title "Electron-spin resonance study of some irradiated D-glucopyranosides" @default.
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- W2080283236 doi "https://doi.org/10.1016/s0008-6215(00)81455-x" @default.
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