Nitramide

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.

Nitramide
Names
Other names
Nitramine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/H2N2O2/c1-2(3)4/h1H2 checkY
    Key: SFDJOSRHYKHMOK-UHFFFAOYSA-N checkY
  • InChI=1/H2N2O2/c1-2(3)4/h1H2
    Key: SFDJOSRHYKHMOK-UHFFFAOYAT
  • N[N+](=O)[O-]
Properties
H2N2O2
Molar mass 62.03 g mol−1
Appearance Colorless solid[1]
Density 1.378 g/cm3
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

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]

Other routes to nitramide include hydrolysis of nitrocarbamic acid,

reaction of sodium sulfamate with nitric acid,

and reaction of dinitrogen pentoxide with two equivalents of ammonia.

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.
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