Chemistry:Nitramide

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Nitramide
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Names
Other names
Nitramine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
Properties
H2N2O2
Molar mass 62.03 g mol−1
Appearance Colorless 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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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

  1. 1.0 1.1 1.2 1.3 Häußler, A.; Klapötke, T. M.; Piotrowski, H. (2002). "Experimental and Theoretical Study on the Structure of Nitramide H2NNO2". Zeitschrift für Naturforschung 57 b (2): 151–156. http://www.znaturforsch.com/ab/v57b/s57b0151.pdf. 
  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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