Nitramide
Chemical compound (H2N–NO2)
From Wikipedia, the free encyclopedia
Nitramide or nitroamine is a chemical compound with the molecular formula H2N−NO2. 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.
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| Names | |||
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| IUPAC name
Nitramide | |||
| Systematic IUPAC name
Nitric amide | |||
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| Properties | |||
| H2N−NO2 | |||
| Molar mass | 62.028 g·mol−1 | ||
| Appearance | Colorless solid[2] | ||
| Density | 1.378 g/cm3 | ||
| Melting point | 72 to 75 °C (162 to 167 °F; 345 to 348 K)[2] | ||
| Acidity (pKa) | 6.5[3] | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Substituted derivatives R1R2N−NO2 are termed nitramides or nitroamines as well and see wide use as explosives: examples include RDX and HMX.
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]
Other routes to nitramide include hydrolysis of nitrocarbamic acid,
- O2N−NH−CO2H → H2N−NO2 + CO2
reaction of sodium sulfamate with nitric acid,
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.
