Nitrosierenden
Nitrosierenden, or nitrosation, is a chemical process that introduces a nitroso group (-NO) into a substrate, forming nitroso derivatives. The reaction is typically electrophilic, proceeding via the nitrosonium ion (NO+) generated in situ from nitrous acid or nitrosating reagents. Common nitrosating agents include nitrous acid (formed from nitrite in acidic media), nitrosyl chloride (NOCl), and nitrosonium salts such as NO+ salts. The substrate’s nucleophilic site—often an amine, a thiol, or an enol—attacks NO+, yielding products such as N-nitrosamines, S-nitrosothiols, or O-nitroso compounds, respectively. Reaction conditions are chosen to control selectivity and minimize side reactions, with temperature and pH playing important roles.
Substrates and product types commonly encountered in nitrosation include:
- Amines, which form N-nitrosamines (R2N-NO). These compounds are used as intermediates in organic synthesis but are
- Thiols, which form S-nitrosothiols (RS-NO), compounds of interest in biochemistry and signaling.
- Alcohols and carbonyl compounds, which can give O-nitroso derivatives or nitroso esters under suitable conditions.
- Aromatic amines, which can yield aryl nitrosamines, a class of compounds with regulatory and safety significance.
Applications include synthesis of nitroso intermediates for further transformations, preparation of signaling-related species in biochemistry, and
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