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The structure of the nitro group

Nitro compounds are organic compounds that contain one or more nitro functional groups (-NO2). They are often highly explosive, especially when the compound contains more than one nitro group and are impure. They are one of the most common explosophores used globally.

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).


Occurrence in Nature

Chloramphenicol is a rare example of a naturally occurring nitro compound. 2-Nitrophenol is an aggregation pheromone of ticks. Two only known examples of aliphatic nitro compounds include 3-nitropropionic acid found in fungi and plants (Indigofera, e.g.), and nitropentadecene, a defense compound found in termites. Many flavin-dependent enzymes are capable of oxidizing aliphatic nitro compounds to less-toxic aldehydes and ketones. Nitroalkane oxidase and 3-nitropropionate oxidase oxidize aliphatic nitro compounds exclusively, whereas other enzymes such as glucose oxidase have other physiological substrates. [1]


In organic synthesis various methods exists to prepare nitro compounds.


Aliphatic nitro compounds

Nitromethane, nitroethane, and nitropropanes are produced industrially by treating propane with nitric acid in the gas phase. Nitromethane can be produced in the laboratory by treating sodium chloroacetate with sodium nitrite, forming sodium bicarbonate and sodium chloride as byproducts.

Aromatic nitro compounds

In a classic electrophilic substitution reaction, nitric acid and sulfuric acid produce the nitronium ion, which reacts with aromatic compounds in aromatic nitration. Another method, starting from halogenated phenols, is the Zinke nitration.


Nitro compounds participate in several organic reactions. Virtually all aromatic amines arise from nitroaromatics.

Aliphatic nitro compounds

The ter Meer reaction
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 protonation to a nitronate 3 and finally nucleophilic displacement of chlorine based on an experimentally observed hydrogen kinetic isotope effect of 3.3 [3]. When the same reactant is reacted with potassium hydroxide the reaction product is the 1,2-dinitro dimer [4]

Aromatic nitro compounds

Nitro compound hydrogenation

See also


  1. ^ Nagpal, Akanksha; Michael P. Valley, Paul F. Fitzpatrick, Allen M. Orville (1/5/2006). "Crystal Structures of Nitroalkane Oxidase: Insights into the Reaction Mechanism from a Covalent Complex of the Flavoenzyme Trapped during Turnover". Biochemistry.  
  2. ^ Edmund ter Meer (1876). "Ueber Dinitroverbindungen der Fettreihe". Justus Liebigs Annalen der Chemie 181 (1): 1–22. doi:10.1002/jlac.18761810102.  
  3. ^ aci-Nitroalkanes. I. The Mechanism of the ter Meer Reaction M. Frederick Hawthorne J. Am. Chem. Soc.; 1956; 78(19) pp 4980 - 4984; doi:10.1021/ja01600a048
  4. ^ 3-Hexene, 3,4-dinitro- D. E. Bisgrove, J. F. Brown, Jr., and L. B. Clapp. Organic Syntheses, Coll. Vol. 4, p.372 (1963); Vol. 37, p.23 (1957). (Article)
  5. ^ Organic Syntheses, Coll. Vol. 5, p.552 (1973); Vol. 47, p.69 (1967).
  6. ^;Baeyer Drewson Indigo Synthesis

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