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Reactions of nitrogen oxide and other reactive nitrogen species with substituted phenols.

Nitric oxide, NO is a stable radical produced in biological systems. In our study we present the reactions of nitric oxide, sodium nitrite and isoamyl nitrite under various conditions with phenols, which are important antioxidants present in biological systems. The reaction of 2,6-di-tertbutyl phenol with nitric oxide in neutral conditions yields 2,6-di-tert-butyl-cyclohexadienone-4-oxime as the major product (90%). The same compound is obtained in acid conditions with sodium nitrite or with isoamyl nitrite. The reactions of p-dihydroxybenzene (hydroquinone) with nitric oxide, sodium nitrite or isoamyl nitrite in similar conditions do not yield any nitrogen containing organic compounds. Instead, quinhydrone, a 1:1 addition compound of hydroquinone and quinone is isolated in high yields (70-90%). Both phenols exclusively form quinone or quinone oxime products in neutral or acidic conditions. However, in basic conditions the yield of quinoid-like products is significant lower (max. 30%). These reactions are pH dependent and GC-MS analyses of the side products formed supports a mechanism, which involves oxidation of the phenol to a phenoxy radical intermediate.

* Hansert, B., Allyn, R.M and Bardhan, R. Department of Biology and Chemistry, Westminster College.
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Title Annotation:Chemistry, Senior Division
Author:Mosher, Mel
Publication:Transactions of the Missouri Academy of Science
Article Type:Abstract
Geographic Code:1U4MO
Date:Jan 1, 2005
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