Nitramide

Nitramide
Other names nitramine
Identifiers
CAS number	7782-94-7
PubChem	24534
ChemSpider	22941 Y
ChEBI	CHEBI:29273 Y
Jmol-3D images	Image 1
SMILES N[N+](=O)[O-]
InChI InChI=1S/H2N2O2/c1-2(3)4/h1H2 Y Key: SFDJOSRHYKHMOK-UHFFFAOYSA-N Y InChI=1/H2N2O2/c1-2(3)4/h1H2 Key: SFDJOSRHYKHMOK-UHFFFAOYAT
Properties
Molecular formula	H2N2O2
Molar mass	62.03 g mol−1
Appearance	colourless solid[1]
Melting point	72-75 °C[1]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 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

References

1. ^ ^{a b c d} Angelika Häußler, Thomas M. Klapötke, and Holger Piotrowski (2002). "Experimental and Theoretical Study on the Structure of Nitramide H₂NNO₂". Z. Naturforsch. 57 b: 151–156. http://www.znaturforsch.com/ab/v57b/s57b0151.pdf. 
2. ^ J. K. Tyler (1963). "Microwave spectrum of nitramide". Journal of Molecular Spectroscopy 11 (1-6): 39–46. doi:10.1016/0022-2852(63)90004-3.