Definitions

nitro group

nitro group

nitro group, in chemistry, functional group that consists of a nitrogen atom joined to two oxygen atoms. Compounds that contain a nitro group, e.g., picric acid and trinitrotoluene (TNT), are called nitro compounds; many nitro compounds are unstable and are used as explosives. As a result of the chemical bonding in the nitro group, the nitrogen atom is positively charged and each oxygen atom has a partial negative charge. For this reason the nitro group has a powerful attraction for electrons. Many of the chemical reactions of nitro compounds are due to this electronegativity of the nitro group.
Nitro compounds are organic compounds that contain one or more nitro functional groups (-2). They are often highly explosive, especially when the compound contains more than one nitro group. The presence of impurities or improper handling can trigger a violent exothermic decomposition.

Aromatic nitro compounds are typically synthesized by the action of a mixture of nitric and sulfuric acids on a suitable organic molecule. Some examples of such compounds are trinitrophenol (picric acid), trinitrotoluene (TNT), and trinitroresorcinol (styphnic acid). Chloramphenicol is a rare example of a naturally occurring nitro compound.

Preparation

In organic synthesis various methods exists to prepare nitro compounds.

Aliphatic nitro compounds

In one study, a reaction mechanism is proposed in which in the first slow step a proton is abstracted from nitroalkane 1 to a carbanion 2 followed by isomerization to a sodium nitronate 3 and finally nucleophilic displacement of chlorine based on an experimentally observed kinetic isotope effect of 3.3 . When the same reactant is reacted with potassium hydroxide the reaction product is the 1,2-dinitro dimer

Aromatic nitro compounds

Reactions

Nitro compounds participate in several organic reactions.

Aliphatic nitro compounds

Aromatic nitro compounds

See also

References

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