Hydrazoic acid

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Hydrazoic acid
Structure, bonding and dimensions of the hydrogen azide molecule
Hydrazoic acid
Hydrazoic acid
Names
IUPAC name
Hydrogen azide
Identifiers
7782-79-8 YesY
ChEBI CHEBI:29449 YesY
ChEMBL ChEMBL186537 YesY
ChemSpider 22937 YesY
Jmol 3D model Interactive image
PubChem 24530
  • InChI=1S/HN3/c1-3-2/h1H YesY
    Key: JUINSXZKUKVTMD-UHFFFAOYSA-N YesY
  • InChI=1/HN3/c1-3-2/h1H
    Key: JUINSXZKUKVTMD-UHFFFAOYAO
  • [N-]=[N+]=[N@H]
Properties
HN3
Molar mass 43.03 g/mol
Appearance colorless, highly volatile liquid
Density 1.09 g/cm3
Melting point −80 °C (−112 °F; 193 K)
Boiling point 37 °C (99 °F; 310 K)
highly soluble
Solubility soluble in alkali, alcohol, ether
Acidity (pKa) 4.6 [1]
Structure
approximately linear
Vapor pressure {{{value}}}
Related compounds
Other cations
Sodium azide
Ammonia
Hydrazine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Hydrazoic acid, also known as hydrogen azide or azoimide,[2] is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, having chemical formula HN3.[3] It was first isolated in 1890 by Theodor Curtius.[4] The acid has few applications, but its conjugate base, the azide ion, is useful in specialized processes.

Hydrazoic acid is soluble in water. Undiluted hydrazoic acid is dangerously explosive with a standard enthalpy of formation ΔfHo (l, 298K) = +264 kJmol−1).[5] When dilute, the gas and aqueous solutions (<10%) can be safely handled.

Production

The acid is usually formed by acidification of an azide salt like sodium azide. Normally solutions of sodium azide in water contain trace quantities of hydrazoic acid in equilibrium with the azide salt, but introduction of a stronger acid can convert the primary species in solution to hydrazoic acid. The pure acid may be subsequently obtained by fractional distillation as an extremely explosive colorless liquid with an unpleasant smell.

NaN3 + HCl → HN3 + NaCl

Its aqueous solution can also be prepared by treatment of barium azide solution with dilute sulfuric acid, filtering the insoluble barium sulfate.[6]

It was originally prepared by the reaction of aqueous hydrazine with nitrous acid.

N2H5+ + HNO2 → HN3 + H+ + 2 H2O

Other oxidizing agents, such as hydrogen peroxide, NOCl, NCl3 or nitric acid, can also be used.[7]

Reactions

In its properties hydrazoic acid shows some analogy to the halogen acids, since it forms poorly soluble (in water) lead, silver and mercury(I) salts. The metallic salts all crystallize in the anhydrous form and decompose on heating, leaving a residue of the pure metal. It is a weak acid (pKa = 4.75.[5]) Its heavy metal salts are explosive and readily interact with the alkyl iodides. Azides of heavier alkali metals (excluding lithium) or alkaline earth metals are not explosive, but decompose in a more controlled way upon heating, releasing spectroscopically-pure N
2
gas.[8] Solutions of hydrazoic acid dissolve many metals (e.g. zinc, iron) with liberation of hydrogen and formation of salts, which are called azides (formerly also called azoimides or hydrazoates).

Dissolution in the strongest acids produces explosive salts containing the H
2
N=N=N+
ion, for example:[8]

HN=N=N + HSbCl
6
[H
2
N=N=N]+
[SbCl
6
]

The ion H
2
N=N=N+
is isoelectronic to diazomethane.

The decomposition of hydrazoic acid, triggered by shock, friction, spark, etc. goes as follows:

2HN
3
H
2
+ 3N
2

Toxicity

Hydrazoic acid is volatile and highly toxic. It has a pungent smell and its vapor can cause violent headaches. The compound acts as a non-cumulative poison.

Applications

2-Furonitrile, a pharmaceutical intermediate and potential artificial sweetening agent has been prepared in good yield by treating furfural with a mixture of hydrazoic acid (HN3) and perchloric acid in the presence of magnesium perchlorate in the benzene solution at 35 °C.[9][10]

The all gas-phase iodine laser (AGIL) mixes gaseous hydrazoic acid with chlorine to produce excited nitrogen chloride, which is then used to cause iodine to lase; this avoids the liquid chemistry requirements of COIL lasers.

References

  1. Pradyot Patnaik. Handbook of Inorganic Chemicals. McGraw-Hill, 2002, ISBN 0-07-049439-8
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  6. L . F. Audrieth, C. F. Gibbs Hydrogen Azide in Aqueous and Ethereal Solution" Inorganic Syntheses 1939, vol. 1, pp. 71-79.
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External links