Nitramide

Nitramide or nitroamine is a chemical compound with the molecular formula H2N\sNO2. Substituted derivatives R^{1}R^{2}N\sNO2 are termed nitramides or nitroamines as well. Organyl derivatives of nitramide, R\sNH\sNO2 and R2N\sNO2, 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\sNO2), in which the hydroxyl group \sOH is replaced with the amino group \sNH2.

Structure
The nitramide molecule is essentially an amine group (\sNH2) bonded to a nitro group (\sNO2). 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\sN−\sCO2−) + 2 H2SO4 → H2N\sNO2 + CO2 + 2 KHSO4

Other routes to nitramide include hydrolysis of nitrocarbamic acid,
 * O2N\sNH\sCO2H → H2N\sNO2 + CO2

reaction of sodium sulfamate with nitric acid,
 * Na(SO3NH2) + HNO3 → H2N\sNO2 + NaHSO4

and reaction of dinitrogen pentoxide with two equivalents of ammonia.
 * N2O5 + 2 NH3 → H2N\sNO2 + [NH4]+NO3−

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