Nitramide

Nitramide

Names
Other names Nitramine
Identifiers
CAS Number	7782-94-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:29273
ChemSpider	22941
PubChem	24534
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	colourless solid[1]
Melting point	72 to 75 °C (162 to 167 °F; 345 to 348 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Nitramide, H₂NNO₂, is a chemical compound. Organyl derivatives of nitramide, RNHNO₂ are termed nitroamines, and are widely used as explosives: examples include RDX and HMX.

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

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.