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 In organic and organometallic chemistry, an organyl group is an organic substituent with one (sometimes more) free valence(-s) at a carbon atom.. The term is often used in chemical patent literature to protect claims over a broad scope. Exam ...

derivatives of nitramide, RNHNO₂ are termed

nitroamine Nitroamines are organic compounds containing a nitro group bonded to an amine. The parent inorganic compound, where R1 = R2 = H, is nitramide Nitramide is a chemical compound with the molecular formula H2NNO2. Organyl derivatives of nitramide, ...

s, 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 RDX (abbreviation of "Research Department eXplosive") or hexogen, among other names, is an organic compound with the formula (O2N2CH2)3. It is a white solid without smell or taste, widely used as an explosive. Chemically, it is classified as a ...

and HMX. It is an isomer of

hyponitrous acid Hyponitrous acid is a chemical compound with formula or HON=NOH. It is an isomer of nitramide, H2N−NO2; and a formal dimer of azanone, HNO. Hyponitrous acid forms two series of salts, the hyponitrites containing the N=NOsup>2− anion, and t ...

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 Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmospher ...

: :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 nitri ...

, :Na(SO₃NH₂) + HNO₃ → O₂NNH₂ + NaHSO₄ and reaction of

dinitrogen pentoxide Dinitrogen pentoxide is the chemical compound with the formula , also known as nitrogen pentoxide or nitric anhydride. It is one of the binary nitrogen oxides, a family of compounds that only contain nitrogen and oxygen. It exists as colourless ...

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 was ...

. :N₂O₅ + 2NH₃ → O₂NNH₂ + NH₄NO₃

Organic nitramides

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

nitrolysis Nitrolysis is a chemical reaction involving cleavage ("lysis") of a chemical bond concomitant with installation of a nitro group (NO2). Typical reagents for effecting this conversion are nitric acid and acetyl nitrate. A commercially important ni ...

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