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Nitroso compounds react with primary amines in acidic environments to form nitrosamines, which human metabolism converts to mutagenic diazo compounds. Small amounts of nitro and nitroso compounds form during meat curing ; the toxicity of these compounds preserves the meat against bacterial infection .
Structural formula of nitroso group. In organic chemistry, nitroso refers to a functional group in which the nitric oxide (−N=O) group is attached to an organic moiety.As such, various nitroso groups can be categorized as C-nitroso compounds (e.g., nitrosoalkanes; R−N=O), S-nitroso compounds (nitrosothiols; RS−N=O), N-nitroso compounds (e.g., nitrosamines, RN(−R’)−N=O), and O ...
A variant on this process with bisulfite is Raschig's hydroxylamine production technique. [12] O-Nitroso compounds are similar to S-nitroso compounds, but are less reactive because the oxygen atom is less nucleophilic than the sulfur atom. The formation of an alkyl nitrite from an alcohol and nitrous acid is a common example: [13]
Nitrosamides are chemical compounds that contain of the chemical structure R 1 C(=X)N(–R 2)–N=O, that is, a nitroso group bonded to the nitrogen of an amide or similar functional group. [1] Specific classes include the N-nitrosamides, N-nitrosoureas, N-nitrosoguanidines, and N-nitrosocarbamates.
Nitrosation follows the classic patterns of electrophilic aromatic substitution (for example, a meta nitro group inhibits the reaction), although substitution ortho to the amine is virtually unknown. The final step, in which a proton eliminates from the Wheland intermediate , appears to be rate-limiting , and the rearrangement is also ...
The C 2 N 2 O core of NDMA is planar, as established by X-ray crystallography. The central nitrogen is bound to two methyl groups and the NO group with bond angles of 120°. The N-N and N-O distances are 1.32 and 1.26 Å, respectively. [14] NDMA forms from a variety of dimethylamine-containing compounds, e.g. hydrolysis of dimethylformamide.
N,N-Diisopropylethylamine, or Hünig's base, is an organic compound that is a tertiary amine. It is named after the German chemist Siegfried Hünig . It is used in organic chemistry as a non-nucleophilic base. It is commonly abbreviated as DIPEA, DIEA, or i-Pr 2 NEt.
N-Nitrosodiethylamine (NDEA) is an organic compound with the formula Et 2 NNO (Et = C 2 H 5). A member of the nitrosamines, it is a light-sensitive, volatile, clear yellow oil that is soluble in water, lipids, and other organic solvents. It has an amine or aromatic odor. It is used as gasoline and lubricant additive, antioxidant, and stabilizer ...