Amine nitration and nitrosation by gaseous nitrogen dioxide.
Reaction of N-methylaniline in solution with ca. 100,000 ppm gaseous NO2 leads to significant amounts of ring- and N-nitro products, in addition to N-methyl-N-nitrosoaniline. Reaction of heterocyclic amines in solution with 5-1000 ppm gaseous NO2 gives significant amounts of N-nitrosamines and much higher amounts of N-nitramines than those obtained from concentrated gaseous NO2. The results are interpreted as evidence that N-nitrosation proceeds via an unsymmetrical ON-ONO2 dimer, whereas N-nitration may involve a free-radical process involving NO2, itself.
D000588:Amines; D000814:Aniline Compounds; D055598:Chemical Phenomena; D002621:Chemistry; D009585:Nitrogen Dioxide; D009602:Nitrosamines / Q000138:chemical synthesis*
D000588:Amines; D000814:Aniline Compounds; D009602:Nitrosamines; D009585:Nitrogen Dioxide; C021313:methylaniline