Nitramide

Nitramide
Names
	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).

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 a tautomer 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]

K₂(O₂NNCO₂) + 2H₂SO₄ → O₂NNH₂ + CO₂ + 2KHSO₄

Other routes to nitramide include hydrolysis of nitrocarbamic acid,

O₂NNHCO₂H → O₂NNH₂ + CO₂

reaction of sodium sulfamate with nitric acid,

Na(SO₃NH₂) + HNO₃ → O₂NNH₂ + NaHSO₄

and reaction of dinitrogen pentoxide with two equivalents of ammonia.

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

^ ^a ^b ^c ^d 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.

[Häußler-1] 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.

[1]

[2]