nitro compound

nitro compound

Any of a class of chemical compounds in which the nitro group (singlehorzbondNO2) forms part of the molecular structure. The most common examples are organic compounds, isomers of nitrite esters in which a carbon atom is linked by a covalent bond to the nitro group's nitrogen atom. Many nitro compounds are commercially used as explosives, solvents, or raw materials and chemical intermediates. They are generally made by a reaction between nitric acid and an organic compound.

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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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