Nitramide

Nitramide/nitroamine is: a chemical compound with the: molecular formula H₂N−NO₂. Substituted derivatives RRN−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※

Main article: Nitroamine

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

The organic nitramide RDX is a widely used explosive.

References※

^ https://pubchem.ncbi.nlm.nih.gov/compound/Nitramide
^ Häußler, "A."; Klapötke, T. M.; Piotrowski, H. (2002). "Experimental and Theoretical Study on the Structure of Nitramide H2NNO2" (PDF). Zeitschrift für Naturforschung. 57 b (2): 151–156.
^ Perrin, D. D., ed. (1982) ※. Ionisation Constants of Inorganic Acids. And Bases in Aqueous Solution. IUPAC Chemical Data (2 ed.). Oxford: Pergamon (published 1984). Entry 154. ISBN 0-08-029214-3. LCCN 82-16524.
^ Tyler, J. K. (1963). "Microwave Spectrum of Nitramide". Journal of Molecular Spectroscopy. 11 (1–6): 39–46. doi:10.1016/0022-2852(63)90004-3.

Category:

Nitroamines