1986
DOI: 10.1002/mrc.1260240304
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ESR and 1H NMR studies of a new class of nitroxyl, nitronylnitroxyl and iminonitroxyl radicals

Abstract: A new synthesis of nitronylnitroxyl (NNR), iminonitroxyl (INR) and nitroxyl radicals (NR) is suggested, involving oxidation of 4H-imidazol di-N-oxides with 0, or PbO, in the presence of nucleophilic reagents. This method allowed the preparation of radicals which could not be synthesized by known procedures. These radicals were studied by ESR and ' H NMR spectroscopy. The hyperfine interaction constants of the NNR were measured and assigned (in some cases radicals containing 15N were used). The influence of pro… Show more

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Cited by 21 publications
(5 citation statements)
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“…A similar observation of proton hyperfine splitting was published by Khramtsov et al [1] for 5,5-dimethyl-2-methoxy-2-(2-methoxycarbonylethyl)-4-phenyl-2,5-dihydroimidazole-1-oxyl 3-oxide [4]. The authors [1] were able to measure the splitting constant of about 0.07 mT assigned to hyperfine interaction with one of the methylene protons of the (CH) 2 COOCH 3 group.…”
Section: Resultssupporting
confidence: 78%
See 1 more Smart Citation
“…A similar observation of proton hyperfine splitting was published by Khramtsov et al [1] for 5,5-dimethyl-2-methoxy-2-(2-methoxycarbonylethyl)-4-phenyl-2,5-dihydroimidazole-1-oxyl 3-oxide [4]. The authors [1] were able to measure the splitting constant of about 0.07 mT assigned to hyperfine interaction with one of the methylene protons of the (CH) 2 COOCH 3 group.…”
Section: Resultssupporting
confidence: 78%
“…The nitroxide radicals of imidazoline and imidazolidine types were shown to reveal the changes in their electron paramagnetic resonance (EPR) spectra due to reversible protonation of N-3 nitrogen [17] of the radical heterocycle and are widely used as pH-probes [4, 5, 14, 15]. However, instability of the paramagnetic N–O· fragment towards chemical reduction is an unavoidable factor that significantly limits their application, particularly in biological systems.…”
Section: Introductionmentioning
confidence: 99%
“…Nevertheless, the analogous breakdown of the series of 3-imidazoline-3-oxide nitroxides with formation of dinitrone 4H-imidazole di-N-oxides was previously described. 52,53 In another report, Karoui et al 16 explained a time-dependent decrease in DEPMPO/GS • adduct with a parallel increase in DEPMPO/CO 2 • adduct upon the photolysis of GSNO, by the formation of CO 2 •radical in the reaction (7) of formate with GS • . The simple kinetic estimates show that in the presence of 20 mM DEPMPO and 400 mM formate, the latter reaction can hardly compete with GS • scavenging by DEPMPO (the ratio k 7 [HCOO -]/k 9b [DEPMPO] ≈ 1.3 × 10 -3 if k 7 ) 10 4 M -1 s -1 , 16 or it is ≈0.1 if k 7 ) 8 × 10 5 M -1 s - 1 23 ).…”
Section: Discussionmentioning
confidence: 98%
“…The appearance of such groups at the carbon a-atom causes a substantial change in the isotropic hfi constant with the nitrogen nucleus and a change in the radical g-factor determined from EPR spectra of radicals in solution. 6 More detailed information about the influence of the 1 5 ~…”
Section: \mentioning
confidence: 99%