Nitramide
Encyclopedia
Nitramide, H2NNO2, is a chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

. Organyl derivatives of nitramide, RNHNO2 are termed nitroamine
Nitroamine
Nitroamines are organic compounds that contain the nitroamino functional group, R2N-NO2. The R's are the continuation of the ring structure, see RDX. Examples of nitroamines are the explosives HMX, cyclotrimethylene trinitramine, Hexanitrohexaazaisowurtzitane and tetryl...

s, and are widely used as explosives: examples include RDX
RDX
RDX, an initialism for Research Department Explosive, is an explosive nitroamine widely used in military and industrial applications. It was developed as an explosive which was more powerful than TNT, and it saw wide use in WWII. RDX is also known as cyclonite, hexogen , and T4...

 and HMX
HMX
HMX, also called octogen, is a powerful and relatively insensitive nitroamine high explosive, chemically related to RDX. Like RDX, the name has been variously listed as High Melting eXplosive, Her Majesty's eXplosive, High-velocity Military eXplosive, or High-Molecular-weight rdX.The molecular...

.

Structure

The nitramide molecule 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,
Na(SO3NH2) + HNO3 → O2NNH2 + NaHSO4


and reaction of dinitrogen pentoxide with two equivalents of ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...

.
N2O5 + 2NH3 → O2NNH2 + NH4NO3
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