Chemistry:Nitramide

Short description: Chemical compound (H₂NNO₂)

Nitramide

Names
IUPAC name Nitramide
Other names Nitramine
Identifiers
CAS Number	7782-94-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29273 Y
ChemSpider	22941 Y
PubChem CID	24534
UNII	B8N6F7BJTL Y
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
SMILES N[N+](=O)[O-]
Properties
Chemical formula	H 2N 2O 2
Molar mass	62.03 g mol−1
Appearance	Colorless solid
Density	1.378 g/cm3
Melting point	72 to 75 °C (162 to 167 °F; 345 to 348 K)
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

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Nitramide is a chemical compound with the molecular formula H
2NNO
2. Organyl derivatives of nitramide, RNHNO
2 are termed nitroamines, and are widely used as explosives: examples include RDX and HMX. It is an isomer of hyponitrous acid.

Structure

The nitramide molecule is essentially an amine group (–NH
2) bonded to a nitro group (–NO
2). 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:

$\mathrm{K}{\phantom{A}}_2(\mathrm{O}{\phantom{A}}_2\mathrm{N}\mathrm{N}\mathrm{C}\mathrm{O}{\phantom{A}}_2)+2\mathrm{H}{\phantom{A}}_2\mathrm{S}\mathrm{O}{\phantom{A}}_4⟶\mathrm{O}{\phantom{A}}_2\mathrm{N}\mathrm{N}\mathrm{H}{\phantom{A}}_2+\mathrm{C}\mathrm{O}{\phantom{A}}_2+2\mathrm{K}\mathrm{H}\mathrm{S}\mathrm{O}{\phantom{A}}_4$

Other routes to nitramide include hydrolysis of nitrocarbamic acid,

$\mathrm{O}{\phantom{A}}_2\mathrm{N}\mathrm{N}\mathrm{H}\mathrm{C}\mathrm{O}{\phantom{A}}_2\mathrm{H}⟶\mathrm{O}{\phantom{A}}_2\mathrm{N}\mathrm{N}\mathrm{H}{\phantom{A}}_2+\mathrm{C}\mathrm{O}{\phantom{A}}_2$

reaction of sodium sulfamate with nitric acid,

$\mathrm{N}\mathrm{a}(\mathrm{S}\mathrm{O}{\phantom{A}}_3\mathrm{N}\mathrm{H}{\phantom{A}}_2)+\mathrm{H}\mathrm{N}\mathrm{O}{\phantom{A}}_3⟶\mathrm{O}{\phantom{A}}_2\mathrm{N}\mathrm{N}\mathrm{H}{\phantom{A}}_2+\mathrm{N}\mathrm{a}\mathrm{H}\mathrm{S}\mathrm{O}{\phantom{A}}_4$

and reaction of dinitrogen pentoxide with two equivalents of ammonia.

$\mathrm{N}{\phantom{A}}_2\mathrm{O}{\phantom{A}}_5+2\mathrm{N}\mathrm{H}{\phantom{A}}_3⟶\mathrm{O}{\phantom{A}}_2\mathrm{N}\mathrm{N}\mathrm{H}{\phantom{A}}_2+\mathrm{N}\mathrm{H}{\phantom{A}}_4\mathrm{N}\mathrm{O}{\phantom{A}}_3$

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.