Nitramide is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

with the molecular formula H₂NNO₂. Organyl derivatives of nitramide, RNHNO₂ are termed nitroamines, and are widely used as

explosive An explosive (or explosive material) is a reactive substance that contains a great amount of potential energy that can produce an explosion if released suddenly, usually accompanied by the production of light, heat, sound, and pressure. An expl ...

s: examples include RDX and

HMX HMX, also called octogen, is a powerful and relatively insensitive nitroamine high explosive, chemically related to RDX. Like RDX, the compound's name is the subject of much speculation, having been variously listed as High Melting Explosive, Her ...

. It is an isomer of hyponitrous acid.

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: :K₂(O₂NNCO₂) + 2H₂SO₄ → O₂NNH₂ + CO₂ + 2KHSO₄ Other routes to nitramide include hydrolysis of nitrocarbamic acid, :O₂NNHCO₂H → O₂NNH₂ + CO₂ reaction of sodium sulfamate with

nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available ni ...

, :Na(SO₃NH₂) + HNO₃ → O₂NNH₂ + NaHSO₄ and reaction of dinitrogen pentoxide with two equivalents of

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous ...

. :N₂O₅ + 2NH₃ → O₂NNH₂ + NH₄NO₃

Organic nitramides

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

hexamethylenetetramine Hexamethylenetetramine, also known as methenamine, hexamine, or urotropin, is a heterocyclic organic compound with the formula (CH2)6N4. This white crystalline compound is highly soluble in water and polar organic solvents. It has a cage-like s ...

References

{{reflist Nitroamines