Nitramide

Nitramide or nitroamine is a chemical compound with the molecular formula H₂N−NO₂. Substituted derivatives R¹R²N−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. Nitroamine
2. Hyponitrous acid
3. H2N2O2
4. Ammonium dinitramide
5. Thiamethoxam
6. Trinitramide
7. Nitrolysis
8. Dinitrogen pentoxide
9. Imidacloprid
10. Tetryl
11. Edwards equation