Polar acidic nitrosamines

X) for VIII (13) y iii) theoretical calculations indicating unusually high contributions of the polar resonance form VII (15) and iv) association with a proton or metal ion at the nitroso oxygen, the site of the highest electron density (14). The structure of nitrosamines is more realistically represented by the resonance hybrid VIII which explains the extraordinary stability of nitrosamines towards acids and bases in contrast to the lability of nitrosamides I under dilute acidic and basic conditions. ... 

At temperatures low enough to suppress thermal decomposition, a nltrosamlde XIV In polar or non-polar solvents Is photolytlcally decomposed to amldyl and nitric oxide radicals 4,16,17,18), This Is In sharp contrast to the photostahility of nitrosamines in neutral solvents (Including acetic acid) (ii), although the pattern of photodecomposition Is similar to that of nitrosamines In dilute acidic conditions. However, the overall photolysis pattern of nltrosamldes Is complicated by disproportionation of nitric oxide and existence of a radical pair XV (20,21,22). ... 

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