Nitramide

Nitramide or nitroamine is a chemical compound with the molecular formula H₂N−NO₂. 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.

Nitramide

Nitrogen, N   Hydrogen, H   Oxygen, O
Names
IUPAC name Nitramide
Systematic IUPAC name Nitric amide
Other names Nitroamide Nitramine[1] Nitroamine[1] Nitroammonia Nitroazane
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
CompTox Dashboard (EPA)	DTXSID20999028
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	H2N−NO2
Molar mass	62.028 g·mol−1
Appearance	Colorless solid[2]
Density	1.378 g/cm3
Melting point	72 to 75 °C (162 to 167 °F; 345 to 348 K)[2]
Acidity (pKa)	6.5[3]
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 [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Substituted derivatives R¹R²N−NO₂ are termed nitramides or nitroamines as well and see wide use as explosives: examples include RDX and HMX.

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,^[4] but planar in the crystal phase.^[2]

Synthesis

Thiele and Lachman's original synthesis of nitramide involved the hydrolysis of potassium nitrocarbamate:^[2]

(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

Main article: Nitroamine

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

The organic nitramide RDX is a widely used explosive.