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Nitramide

Nitrogen, N  Hydrogen, H  Oxygen, O
Names
IUPAC name Nitramide
Systematic IUPAC name Nitric amide
Other names Nitroamide Nitramine Nitroamine Nitroammonia Nitroazane
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/h1H2Key: SFDJOSRHYKHMOK-UHFFFAOYSA-N InChI=1/H2N2O2/c1-2(3)4/h1H2Key: SFDJOSRHYKHMOK-UHFFFAOYAT
SMILES N(=O)
Properties
Chemical formula	H2N−NO2
Molar mass	62.028 g·mol
Appearance	Colorless solid
Density	1.378 g/cm
Melting point	72 to 75 °C (162 to 167 °F; 345 to 348 K)
Acidity (pKa)	6.5
Related compounds
Related compounds	Ammonia Dinitramide Ammonium dinitramide Trinitramide Nitryl fluoride Nitryl chloride Nitryl bromide Nitryl iodide Nitric acid Dinitrogen trioxide Dinitrogen tetroxide Dinitrogen pentoxide Nitromethane Hexamethylenetetramine HMX
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is  ?) Infobox references

Nitramide or nitroamine is a chemical compound with the molecular formula H₂N−NO₂. Substituted derivatives RRN−NO₂ are termed nitramides or nitroamines as well. Organyl derivatives of nitramide, R−NH−NO₂ and R₂N−NO₂, are widely used as explosives: examples include RDX and HMX. It is an isomer of hyponitrous acid. Nitramide can be viewed as a nitrogen analog of nitric acid (HO−NO₂), in which the hydroxyl group −OH is replaced with the amino group −NH₂.

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, but planar in the crystal phase.

Synthesis

Thiele and Lachman's original synthesis of nitramide involved the hydrolysis of potassium nitrocarbamate:

(K)₂(O₂N−N−CO−2) + 2 H₂SO₄ → H₂N−NO₂ + CO₂ + 2 KHSO₄

Other routes to nitramide include hydrolysis of nitrocarbamic acid,

O₂N−NH−CO₂H → H₂N−NO₂ + CO₂

reaction of sodium sulfamate with nitric acid,

Na(SO₃NH₂) + HNO₃ → H₂N−NO₂ + NaHSO₄

and reaction of dinitrogen pentoxide with two equivalents of ammonia.

N₂O₅ + 2 NH₃ → H₂N−NO₂ + [NH₄]NO−3

Organic nitramides

Also called nitramines, organic nitramides are important explosives. They are prepared by nitrolysis of hexamethylenetetramine.

References

1. ^ "Nitramide".
2. ^ 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. doi:10.1515/znb-2002-0204.
3. Perrin, D. D., ed. (1982) . Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 154. ISBN 0-08-029214-3. LCCN 82-16524.
4. Tyler, J. K. (1963). "Microwave Spectrum of Nitramide". Journal of Molecular Spectroscopy. 11 (1–6): 39–46. Bibcode:1963JMoSp..11...39T. doi:10.1016/0022-2852(63)90004-3.

• Nitroamines