Nitramide

Nitramide
Nitrogen, N Hydrogen, H Oxygen, O
Names
	IUPAC name Nitramide
	Systematic IUPAC name Nitric amide
	Other names Nitroamide; Nitramine; Nitroamine; Nitroammonia; Nitroazane;
Identifiers
CAS Number	7782-94-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:29273 ;
ChemSpider	22941 ;
PubChem CID	24534;
UNII	B8N6F7BJTL ;
CompTox Dashboard (EPA)	DTXSID20999028 ;
	InChI InChI=1S/H2N2O2/c1-2(3)4/h1H2 Key: SFDJOSRHYKHMOK-UHFFFAOYSA-N ; InChI=1/H2N2O2/c1-2(3)4/h1H2 Key: SFDJOSRHYKHMOK-UHFFFAOYAT;
	SMILES N[N+](=O)[O-];
Properties
Chemical formula	H2N−NO2
Molar mass	62.028 g·mol−1
Appearance	Colorless solid
Density	1.378 g/cm3
Melting point	72 to 75 °C (162 to 167 °F; 345 to 348 K)
Acidity (pKa)	6.5
Related compounds
Related compounds	Ammonia; Dinitramide; Ammonium dinitramide; Trinitramide; Nitryl fluoride; Nitryl chloride; Nitryl bromide; Nitryl iodide; Nitric acid; Dinitrogen trioxide; Dinitrogen tetroxide; Dinitrogen pentoxide; Nitromethane; Hexamethylenetetramine; HMX;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Nitramide or nitroamine is a chemical compound with the molecular formula H₂N−NO₂. Substituted derivatives R¹R²N−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,^[4] but planar in the crystal phase.^[2]

Synthesis

Thiele and Lachman's original synthesis of nitramide involved the hydrolysis of potassium nitrocarbamate:^[2]

(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

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

^ ^a ^b "Nitramide".
^ ^a ^b ^c ^d 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. doi:10.1515/znb-2002-0204.
^ Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd 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. Bibcode:1963JMoSp..11...39T. doi:10.1016/0022-2852(63)90004-3.

[pubchem-1] "Nitramide".

[Häußler-2] 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. doi:10.1515/znb-2002-0204.

[P82db-3] Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 154. ISBN 0-08-029214-3. LCCN 82-16524.

[4] Tyler, J. K. (1963). "Microwave Spectrum of Nitramide". Journal of Molecular Spectroscopy. 11 (1–6): 39–46. Bibcode:1963JMoSp..11...39T. doi:10.1016/0022-2852(63)90004-3.

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