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Nitro compound



  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. 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.

Additional recommended knowledge

Contents

Preparation

In organic synthesis various methods exists to prepare nitro compounds.

Aliphatic nitro compounds

[1] the reactant is a 1,1-halonitroalkane:

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 [2]. When the same reactant is reacted with potassium hydroxide the reaction product is the 1,2-dinitro dimer [3]

Aromatic nitro compounds

Reactions

Nitro compounds participate in several organic reactions.

Aliphatic nitro compounds

Aromatic nitro compounds

See also

References

  1. ^ Edm. ter Meer (1876). "Ueber Dinitroverbindungen der Fettreihe". Justus Liebigs Annalen der Chemie 181 (1): 1 - 22. doi:10.1002/jlac.18761810102.
  2. ^ 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
  3. ^ 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)
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Nitro_compound". A list of authors is available in Wikipedia.
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