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Reducing Power of Simple Polyphenols by Electron-Transfer Reactions Using a New Stable Radical of the PTM Series, Tris (2,3,5,6-tetrachloro-4-nitrophenyl)methyl Radical.

AutorTorres, Josep Lluís; Carreras, Anna; Jiménez, Aurora; Brillas, Enric; Torrelles, Xavier ; Rius, Jordi ; Juliá, Lluís
Palabras claveElectron-transfer
Stable radicals
Fecha de publicación17-abr-2007
EditorAmerican Chemical Society
CitaciónThe Journal of Organic Chemistry, 72(10): 3750-3756 (2007)
ResumenThe synthesis and characterization of a new radical and its use for testing the antioxidant activity of polyphenols by electron transfer are reported. This new and stable species of magnetic nature, tris-(2,3,5,6-tetrachloro-4-nitrophenyl)methyl (TNPTM) radical, has been characterized by electron paramagnetic resonance and its molecular structure determined by X-ray analysis. This new radical of the PTM (perchlorotriphenylmethyl) series, unlike 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, is stable in conditions of hydrogen abstraction reactions. TNPTM radical is able to discriminate between the antioxidant activities of catechol and pyrogallol in hydroxylated solvent mixtures such as chloroform/methanol (2:1). These features determine the antioxidant/pro-oxidant character and the biological activities of natural and synthetic flavonoids.
Descripción7 pages, 3 figures.-- PMID: 17439176 [PubMed].
Supporting information (15 pages) available at: http://pubs.acs.org/doi/suppl/10.1021/jo062665a/suppl_file/jo062665asi20070314_072402.pdf
Supplementary Crystallographic Information File available at: http://pubs.acs.org/doi/suppl/10.1021/jo062665a/suppl_file/jo062665asi20070315_085423.cif
Versión del editorhttp://dx.doi.org/10.1021/jo062665a
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