7-Ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone (echinochrome A): a DFT study of the antioxidant mechanism 2.* The structure of monosodium salts of echinochrome A and their reactions with the hydroperoxyl radical

被引：0
作者：
V. P. Glazunov
D. V. Berdyshev
V. L. Novikov
机构：
[1] Far-Eastern Branch of the Russian Academy of Sciences,Pacific Institute of Bioorganic Chemistry
来源：
Russian Chemical Bulletin | 2010年 / 59卷
关键词：
Key words; density functional theory; conformational analysis; polyhydroxy-1,4-naphtho-quinones; echinochrome A; sodium salts of echinochrome A; antioxidant; hydroperoxyl radical; bond dissociation energy; homolysis; heterolysis;
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摘要：
The relative gas-phase acidities of all OH groups of 7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone (echinochrome A, 1) were evaluated by the B3LYP/6-311G(d) and B3LYP/6-311G(d,p) methods. Calculations predict that gB-OH groups at the C(2) and C(6) atoms are the most acidic in molecule 1and their acidity is higher than that of o-nitrophenol. Conformational analysis of undissociated monosodium salts of 1and their radicals was performed. It was shown that gas-phase quenching reactions of the hydroperoxyl radical by mono-sodium salts of 1are exothermic.
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页码：43 / 54
页数：11
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