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

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

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 1 and the...

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Veröffentlicht in:Russian chemical bulletin 2010, Vol.59 (1), p.43-54
Hauptverfasser: Glazunov, V. P., Berdyshev, D. V., Novikov, V. L.
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Inorganic Chemistry
Organic Chemistry
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Zusammenfassung: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 1 and their acidity is higher than that of o -nitrophenol. Conformational analysis of undissociated monosodium salts of 1 and their radicals was performed. It was shown that gas-phase quenching reactions of the hydroperoxyl radical by mono-sodium salts of 1 are exothermic.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-010-0043-1