In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (−NO2). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitro group is also strongly electron-withdrawing. Because of this property, C−H bonds alpha (adjacent) to the nitro group can be acidic. For similar reasons, the presence of nitro groups in aromatic compounds retards electrophilic aromatic substitution but facilitates nucleophilic aromatic substitution. Nitro groups are rarely found in nature. They are almost invariably produced by nitration reactions starting with nitric acid.
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In this Dossier
- ⭐ Core Definition: Nitro group
- Nitro group in the context of Nitration
- Nitro group in the context of Nitroimidazole
Nitro group in the context of Nitration
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group (−NO2) into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters (−ONO2) between alcohols and nitric acid (as occurs in the synthesis of nitroglycerin). The difference between the resulting molecular structures of nitro compounds and nitrates (NO−3) is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom (typically carbon or another nitrogen atom), whereas in nitrate esters (also called organic nitrates), the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom (nitrito group).
There are many major industrial applications of nitration in the strict sense; the most important by volume are for the production of nitroaromatic compounds such as nitrobenzene. The technology is long-standing and mature.
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Nitroimidazoles are the group of organic compounds consisting of an imidazole ring with at least one nitro group substituent. The term also refers to the class of antibiotics that have nitroimidazole in their structures. These antibiotics commonly include the 5-nitroimidazole positional isomer.
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