Nitro compound

(Redirected from Nitroparaffins)
Jump to: navigation, search
File:Nitro-group-2D.png
The structure of the nitro group

Nitro compounds are organic compounds that contain one or more nitro functional groups (-Template:NitrogenO2). They are often highly explosive; various impurities or improper handling can easily 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).

Preparation

In organic synthesis various methods exists to prepare nitro compounds.

Aliphatic nitro compounds

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

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 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)

de:Organische Nitroverbindung it:Nitrocomposti lv:Nitrosavienojumi


Linked-in.jpg