Reaction with nitrogen dioxide

The reaction of nitric oxide with nitrogen dioxide in the gas phase 

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From a practical point of view, nitrogen dioxide is not a satisfactory oxidant for the preparation of D-glucuronic acid. Anhydrous conditions of reaction are generally necessary and the oxidation progresses slowly. Periods of at least nine hours are required for completion of an oxidation when liquid nitrogen dioxide is used. Reactions with nitrogen dioxide in chloroform solution or in the gaseous state take a number of days. Side reactions occur to some extent, and lower the yield of the main product. 

The irradiation of nitrate in the presence of 2-phenylphenol yields oxidation (phenylhydroquinone, phenylbenzoquinone, 2-hydroxydibenzofuran) and nitration intermediates (2-hydroxy-3-nitrobiphenyl and 2-hydroxy-5-nitrobiphenyl) [124]. 2-Hydroxydibenzofuran is formed by photocyclisation of phenylbenzoquinone. Nitration might be due to reaction with nitrogen dioxide, but an interesting aspect is the effect of pH. The fact that nitration is favoured at low pH might indicate a role of photoformed nitrous acid, due to either photochemical or dark reactivity [124], It is worth noting that the... 

Nitrogen oxides other than nitrogen dioxide have been studied for possible adverse health effects. Chemical analysis of ambient aerosols collected in southern California has revealed that nitrates exhibit particularly high values compared to other parts of the United States. These aerosols are generally acidic in nature and are composed of nitric acid and nitrate salts that are formed through photochemical reactions with nitrogen dioxide and other oxides of... 

It is also possible that NO3 plays some part in these sensitized ignitions. It could be formed by the reaction NO -f O2 —> NO3 and either start hydrogen-oxygen chains by reaction with hydrogen or be removed by the rapid reaction with nitric oxide NO NOs 2NO2, and by the less rapid reaction with nitrogen dioxide. This may tend to decrease the sensitizing effect of nitric oxide. 

Ren, J. Sakakibara, K. Hirota, M. The synthesis of poly[iV-(p-vinylbenzylidene)-tert-butylamine iV-oxide] and characterizations of reaction with nitrogen dioxide. Bull. Chem. Soc. Jpn. 1993, 66, 1897-1902. 

Slagle, I.R., Gutman, D. (1982) Kinetics of Free Radicals Produced by Infrared Multiphoton-induced Decomposition. 2. Formation of Acetyl and Dichlorofluo-romethyl Radicals and Their Reactions with Nitrogen Dioxide. J. Am. Chem. Soc. 104 4741-4748. 

The scheme of processes of the PVP conversion in reactions with nitrogen dioxide is shown below. 

The end groups introduced by the short-stop mixture evidently arise from reaction with nitrogen dioxide. This molecule is a resonance hybrid which may be represented by the canonical electronic struc-... 

Its disappearance occurs at night in reaction with nitrogen dioxide too ... 

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