Nitrosation
Encyclopedia
Nitrosation is a process of converting organic compounds into nitroso
derivatives, i.e. compounds containing the R-NO functionality.
compounds, such as nitrosobenzene
, are typically prepared by oxidation of hydroxylamines:
sources with amino compounds
. Typically this reaction proceeds via the attack of the nitrosonium
electrophile on an amine:
Nitroso
Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds are a class of organic compounds containing the nitroso functional group, R−N=O....
derivatives, i.e. compounds containing the R-NO functionality.
C-Nitroso compounds
C-NitrosoNitroso
Nitroso refers to a functional group in organic chemistry which has the general formula RNO. Nitroso compounds are a class of organic compounds containing the nitroso functional group, R−N=O....
compounds, such as nitrosobenzene
Nitrosobenzene
Nitrosobenzene is the organic compound with the formula C6H5NO. The compound can be viewed as hybrid of singlet O2 and azobenzene. This diamagnetic species exists in equilibrium with its dimer.-Preparation:...
, are typically prepared by oxidation of hydroxylamines:
- RNHOH + [O] → RNO + H2O
N-nitrosamines
N-nitrosamines, including the carcinogenic variety, arise from the reaction of nitriteNitrite
The nitrite ion has the chemical formula NO2−. The anion is symmetric with equal N-O bond lengths and a O-N-O bond angle of ca. 120°. On protonation the unstable weak acid nitrous acid is produced. Nitrite can be oxidised or reduced, with product somewhat dependent on the oxidizing/reducing agent...
sources with amino compounds
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
. Typically this reaction proceeds via the attack of the nitrosonium
Nitrosonium
The nitrosonium ion is NO+, in which the nitrogen atom is bonded to an oxygen atom with a bond order of 3, and the overall diatomic species bears a positive charge. This ion is usually obtained as the following salts: NOClO4, NOSO4H , and NOBF4. The ClO and BF salts are slightly soluble in CH3CN...
electrophile on an amine:
- NO2- + 2 H+ → NO+ + H2O
- R2NH + NO+ → R2N-NO + H+