Reactions of arylamine and aminophenol derivatives, and riboflavin with organic radicals.
Based on product yield data on radiolysis of hexane, ethanol and 3 M aqueous ethylene glycol solutions, the ability of a number of arylamine, aminophenol and quinonimine derivatives to affect processes involving peroxyl, alkyl or alpha-hydroxyalkyl radicals was assessed. It has been shown that the introduction of a hydroxyl group into aromatic amine structure enhances its antioxidant performance and makes it significantly more reactive with respect to carbon-centered organic radicals. Replacement of the hydrogen atom of a hydroxyl group by a methyl group decreases the anti-radical activity of aminophenols drastically. Compounds containing (or capable of forming) a quinonimine moiety interact with alkyl or alpha-hydroxyalkyl radicals most effectively, suppressing recombination and fragmentation reactions of the latter. In the sequence: aromatic amines--aminophenols--quinonimines, a trend towards enhancement of the ability of the compounds studied to react with carbon-centered radicals was noted. Also, this study presents for the first time evidence of riboflavin reactivity with respect to organic radicals.
Ksendzova
G A
GA
Research Institute for Physical Chemical Problems, Belarusian State University, Leningradskaya st.14, 220050 Minsk, Republic of Belarus.
Sorokin
V L
VL
Edimecheva
I P
IP
Shadyro
O I
OI
D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D000627:Aminophenols / Q000737:chemistry* / Q000494:pharmacology; D005609:Free Radicals / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry; D012256:Riboflavin / Q000737:chemistry* / Q000494:pharmacology
D000588:Amines; D000627:Aminophenols; D005609:Free Radicals; D010545:Peroxides; D012256:Riboflavin