Organonitrogen compounds. 386

Organic nitrogen compounds that may be found as atmospheric contaminants can be classified as amines, amides, nitriles, nitro compounds, or heterocyclic nitrogen compounds. Structures of 

FIGURE 7.11 Common organosulfur compounds associated with air pollution. The organosulfur compounds are especially noted for their strong odors. 

FIGURE 7.12 Organonitrogen compounds that may be encountered as air pollutants. 

Though probably not toxic at levels found in the ambient atmosphere, organonitrogen compounds can be harmful in the workplace atmosphere. The lower aliphatic amines are among the more toxic substances in routine, large-scale use. They are basic compounds that hydrolyze to raise the pH in tissue that they contact as shown below for monomethylamine  

Lungs exposed to the lower amines can exhibit hemorrhage and edema (excessive fluid accumulation). Aniline and nitrobenzene may cause the iron(II) in blood hemoglobin to be oxidized to iron(HI) so that the blood no longer transports oxygen. Some of the aromatic amines are known human carcinogens. Two important examples are 1-naphthylamine and 2-naphthylamine, which were shown to cause bladder cancer in German dye industry workers exposed to these compounds around 1900. 

---

Table 2.3. Chemical shift ranges for organonitrogen compounds...

The most broadly studied organic nitrogen compound is probably quinoline however, most studies report biodegradation. As we have seen from Table 14, quinoline is representative of the organonitrogen compounds present in the diesel cut. Its transformation has been studied in both, anaerobic and aerobic conditions. Several metabolic pathways have been proposed to explain the aerobic transformations however, no pathway has been proposed for quinoline metabolism under anaerobic conditions. 

The Nitrogen Availability Assay [376] consists of growth tests under defined conditions using mineral salts medium and organonitrogen compounds as sources of carbon and/or nitrogen. Probe molecules include quinoline, pyridine, carbazole, and porphyrin. Growth tests are performed using six conditions ... 

Having acquired the ground rules of alkali metal organonitrogen compound aggregation as outlined in the previous section, how does one begin to generate new architectures and, as structure is intimately linked to reactivity, new chemistry, i.e., how can we synthesize new metal-organonitrogen compounds which do not con-... 

Several different organonitrogen compounds readily undergo metal-catalyzed oxidation using alkyl hydroperoxide or hydrogen peroxide as oxygen transfer agents. In 1961,... 

Oxidation of organonitrogen compounds is an important process from both industrial and synthetic viewpoints . N-oxides are obtained by oxidation of tertiary amines (equation 52), which in some cases may undergo further reactions like Cope elimination and Meisenheimer rearrangement . The oxygenation products of secondary amines are generally hydroxylamines, nitroxides and nitrones (equation 53), while oxidation of primary amines usually afforded oxime, nitro, nitroso derivatives and azo and azoxy compounds through coupling, as shown in Scheme 17. Product composition depends on the oxidant, catalyst and reaction conditions employed. 

Organonitrogen compounds are quite stable throughout most refining processes. Basic heteroatomic species such as pyridine and quinoline can be found as well as nonbasic pyrrole and indole compounds. 

---