Nitramide

Nitramide
Names
	IUPAC name Nitramide
	Other names Nitramine
Identifiers
CAS Number	7782-94-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29273 ;
ChemSpider	22941 ;
PubChem CID	24534;
UNII	B8N6F7BJTL ;
CompTox Dashboard (EPA)	DTXSID20999028 ;
	InChI InChI=1S/H2N2O2/c1-2(3)4/h1H2 Key: SFDJOSRHYKHMOK-UHFFFAOYSA-N ; InChI=1/H2N2O2/c1-2(3)4/h1H2 Key: SFDJOSRHYKHMOK-UHFFFAOYAT;
	SMILES N[N+](=O)[O-];
Properties
Chemical formula	H2N2O2
Molar mass	62.03 g mol−1
Appearance	Colorless solid
Density	1.378 g/cm3
Melting point	72 to 75 °C (162 to 167 °F; 345 to 348 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Nitramide is a chemical compound with the molecular formula H₂NNO₂. Organyl derivatives of nitramide, RNHNO₂ are termed nitroamines, and are widely used as explosives: examples include RDX and HMX. It is an isomer of hyponitrous acid.

Structure

The nitramide molecule is essentially an amine group (−NH₂) bonded to a nitro group (−NO₂). It is reported to be non-planar in the gas phase,^[2] but planar in the crystal phase.^[1]

Synthesis

Thiele and Lachman's original synthesis of nitramide involved the hydrolysis of potassium nitrocarbamate:^[1]

{\ce {K2(O2NNCO2) + 2H2SO4 -> O2NNH2 + CO2 + 2KHSO4}}

Other routes to nitramide include hydrolysis of nitrocarbamic acid,

{\ce {O2NNHCO2H -> O2NNH2 + CO2}}

reaction of sodium sulfamate with nitric acid,

{\ce {Na(SO3NH2) + HNO3 -> O2NNH2 + NaHSO4}}

and reaction of dinitrogen pentoxide with two equivalents of ammonia.

{\ce {N2O5 + 2NH3 -> O2NNH2 + NH4NO3}}

Organic nitramides

Also called nitramines, organic nitramides are important explosives. They are prepared by nitrolysis of hexamethylenetetramine.

The organic nitramide RDX is a widely used explosive.

References

1 2 3 4 Häußler, A.; Klapötke, T. M.; Piotrowski, H. (2002). "Experimental and Theoretical Study on the Structure of Nitramide H2NNO2" (PDF). Zeitschrift für Naturforschung. 57 b (2): 151–156.
↑ Tyler, J. K. (1963). "Microwave Spectrum of Nitramide". Journal of Molecular Spectroscopy. 11 (1–6): 39–46. doi:10.1016/0022-2852(63)90004-3.

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[Häußler-1] 1 2 3 4 Häußler, A.; Klapötke, T. M.; Piotrowski, H. (2002). "Experimental and Theoretical Study on the Structure of Nitramide H2NNO2" (PDF). Zeitschrift für Naturforschung. 57 b (2): 151–156.

[2] Tyler, J. K. (1963). "Microwave Spectrum of Nitramide". Journal of Molecular Spectroscopy. 11 (1–6): 39–46. doi:10.1016/0022-2852(63)90004-3.

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