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Nitro compound
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===Preparation of aromatic nitro compounds === [[File:PhNO2&metric.png|class=skin-invert-image|thumb|144px|Structural details of [[nitrobenzene]], distances in picometers.<ref>{{cite journal |journal=Structural Chemistry |year=2007 |volume=18 |issue=6 |pages=739–753 |title=Molecular Structure and Conformation of Nitrobenzene Reinvestigated by Combined Analysis of Gas-Phase Electron Diffraction, Rotational Constants, and Theoretical Calculations |author=Olga V. Dorofeeva |author2=Yuriy V. Vishnevskiy |author3=Natalja Vogt |author4=Jürgen Vogt |author5=Lyudmila V. Khristenko |author6=Sergey V. Krasnoshchekov |author7=Igor F. Shishkov |author8=István Hargittai |author9=Lev V. Vilkov |doi=10.1007/s11224-007-9186-6 |s2cid=98746905}}</ref>]] Aromatic nitro compounds are typically synthesized by nitration. Nitration is achieved using a mixture of [[nitric acid]] and [[sulfuric acid]], which produce the [[nitronium]] ion ({{chem2|NO2+}}), which is the electrophile: <div>{{pad|1em}}[[File:Benzol.svg|class=skin-invert-image|x60px|Benzene]] + [[File:Nitronium ion vert.svg|class=skin-invert-image|x60px|Nitronium ion]] {{Biochem reaction subunit|direction=forward|for_prod={{H+|nolink=y}}|imagesize=60px|container_style=vertical-align:middle}} [[File:Nitrobenzol.svg|class=skin-invert-image|x100px|Nitrobenzene]]</div> The nitration product produced on the largest scale, by far, is [[nitrobenzene]]. Many explosives are produced by nitration including [[trinitrophenol]] (picric acid), [[trinitrotoluene]] (TNT), and [[trinitroresorcinol]] (styphnic acid).<ref>{{Ullmann|last=Gerald|first=Booth|title=Nitro Compounds, Aromatic|doi=10.1002/14356007.a17_411}}</ref> Another but more specialized method for making aryl–NO<sub>2</sub> group starts from halogenated phenols, is the [[Zinke nitration]].
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