{{Short description|Chemical compound (H2N–NO2)}} {{chembox | Watchedfields = changed | verifiedrevid = 444027016 | Name = Nitramide | ImageFile = Nitramide-resonance-2D.png | ImageSize = 250 | ImageFileL1 = Nitramide-3D-balls.png | ImageSizeL1 = | ImageCaptionL1 = {{legend|blue|Nitrogen, N}}{{legend|white|Hydrogen, H}}{{legend|red|Oxygen, O}} | ImageFileR1 = Nitramide-3D-vdW.png | ImageSizeR1 = | IUPACName = Nitramide | OtherNames = {{ubl|Nitroamide|Nitramine<ref name=pubchem>{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Nitramide | title=Nitramide }}</ref>|Nitroamine<ref name=pubchem />|Nitroammonia|Nitroazane}} | SystematicName = Nitric amide | Section1 = {{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 22941 | InChI = 1/H2N2O2/c1-2(3)4/h1H2 | InChIKey = SFDJOSRHYKHMOK-UHFFFAOYAT | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/H2N2O2/c1-2(3)4/h1H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = SFDJOSRHYKHMOK-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|??}} | CASNo = 7782-94-7 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = B8N6F7BJTL | PubChem = 24534 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 29273 | SMILES = N[N+](=O)[O-] }} | Section2 = {{Chembox Properties | Formula = {{chem2|H2N\sNO2}} | H=2|N=2|O=2 | Appearance = Colorless solid<ref name="Häußler">{{cite journal |author1=Häußler, A. |author2=Klapötke, T. M. |author3=Piotrowski, H. | title = Experimental and Theoretical Study on the Structure of Nitramide H2NNO2 | journal = Zeitschrift für Naturforschung | year = 2002 | volume = 57 b | issue = 2 | pages = 151–156 |doi=10.1515/znb-2002-0204 | url = http://www.znaturforsch.com/ab/v57b/s57b0151.pdf}}</ref> | Density = 1.378 g/cm<sup>3</sup> | MeltingPtC = 72 to 75 | MeltingPt_ref = <ref name="Häußler" /> | pKa = 6.5<ref name=P82db>{{cite book|title=Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution|editor-first=D. D.|editor-last=Perrin|edition=2nd|series=IUPAC Chemical Data|issue=29|publisher=Pergamon|location=Oxford|year=1982|publication-date=1984|orig-date=1969|lccn=82-16524|isbn=0-08-029214-3|at=Entry 154}}</ref>}} | Section8 = {{Chembox Related | OtherCompounds = {{ubl|Ammonia|Dinitramide|Ammonium dinitramide|Trinitramide|Nitryl fluoride|Nitryl chloride|Nitryl bromide|Nitryl iodide|Nitric acid|Dinitrogen trioxide|Dinitrogen tetroxide|Dinitrogen pentoxide|Nitromethane|Hexamethylenetetramine|HMX}} }} }}
'''Nitramide''' or '''nitramine''' is a chemical compound with the molecular formula {{chem2|H2N\sNO2|auto=1}}. It is an isomer of hyponitrous acid. Nitramide can be viewed as a nitrogen analog of nitric acid ({{chem2|HO\sNO2}}), in which the hydroxyl group {{chem2|\sOH}} is replaced with the amino group {{chem2|\sNH2}}.
Substituted derivatives {{chem2|R^{1}R^{2}N\sNO2}} are termed nitramides or nitroamines as well and see wide use as explosives: examples include RDX and HMX.
== Structure == The nitramide molecule is essentially an amine group ({{chem2|\sNH2}}) bonded to a nitro group ({{chem2|\sNO2}}). It is reported to be non-planar in the gas phase,<ref>{{cite journal | author = Tyler, J. K. | title = Microwave Spectrum of Nitramide | journal = Journal of Molecular Spectroscopy | year = 1963 | volume = 11 | issue = 1–6 | pages = 39–46 | doi = 10.1016/0022-2852(63)90004-3| bibcode = 1963JMoSp..11...39T }}</ref> but planar in the crystal phase.<ref name="Häußler" />
== Synthesis == Thiele and Lachman's original synthesis of nitramide involved the hydrolysis of potassium nitrocarbamate:<ref name="Häußler" />
:{{chem2|(K+)2(O2N\sN−\sCO2−) + 2 H2SO4 → H2N\sNO2 + CO2 + 2 KHSO4}}
Other routes to nitramide include hydrolysis of nitrocarbamic acid, :{{chem2|O2N\sNH\sCO2H → H2N\sNO2 + CO2}}
reaction of sodium sulfamate with nitric acid, :{{chem2|Na(SO3NH2) + HNO3 → H2N\sNO2 + NaHSO4}}
and reaction of dinitrogen pentoxide with two equivalents of ammonia. :{{chem2|N2O5 + 2 NH3 → H2N\sNO2 + [[Ammonium nitrate|[NH4]+NO3−]]}}
==Organic nitramides== {{Main|Nitroamine}} Also called nitramines, organic nitramides are important explosives. They are prepared by nitrolysis of hexamethylenetetramine. [[File:RDX.svg|thumb|left|180 px|The organic nitramide RDX is a widely used explosive.]]{{clear left}}
==References== {{reflist}}
Category:Nitroamines