Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Hydrazoic acid, also known as hydrogen azide, azic acid or azoimide,[2] is a compound with the chemical formula HN3.[3] It is a colorless, volatile, and explosive liquid at room temperature and pressure. It is a compound of nitrogen and hydrogen, and is therefore a pnictogen hydride. The oxidation state of the nitrogen atoms in hydrazoic acid is fractional and is -1/3.[citation needed] 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, like its fellow mineral acids, is soluble in water. Undiluted hydrazoic acid is dangerously explosive[5] with a standard enthalpy of formation ΔfHo (l, 298K) = +264 kJ/mol.[6] When dilute, the gas and aqueous solutions (<10%) can be safely prepared but should be used immediately; because of its low boiling point, hydrazoic acid is enriched upon evaporation and condensation such that dilute solutions incapable of explosion can form droplets in the headspace of the container or reactor that are capable of explosion.[7][8]
^Pradyot Patnaik. Handbook of Inorganic Chemicals. McGraw-Hill, 2002, ISBN 0-07-049439-8
^Chisholm, Hugh, ed. (1911). "Azoimide" . Encyclopædia Britannica. Vol. 3 (11th ed.). Cambridge University Press. pp. 82–83. This also contains a detailed description of the contemporaneous production process.
^Dictionary of Inorganic and Organometallic Compounds. Chapman & Hall.
^Curtius, Theodor (1890). "Ueber Stickstoffwasserstoffsäure (Azoimid) N3H" [On hydrazoic acid (azoimide) N3H]. Berichte der Deutschen Chemischen Gesellschaft. 23 (2): 3023–3033. doi:10.1002/cber.189002302232.
^Furman, David; Dubnikova, Faina; van Duin, Adri C. T.; Zeiri, Yehuda; Kosloff, Ronnie (2016-03-10). "Reactive Force Field for Liquid Hydrazoic Acid with Applications to Detonation Chemistry". The Journal of Physical Chemistry C. 120 (9): 4744–4752. Bibcode:2016APS..MARH20013F. doi:10.1021/acs.jpcc.5b10812. ISSN 1932-7447. S2CID 102029987.
^Cite error: The named reference InorgChem was invoked but never defined (see the help page).
^Gonzalez-Bobes, F. et al Org. Process Res. Dev. 2012, 16, 2051-2057.
^Treitler, D. S. et al Org. Process Res. Dev. 2017, 21, 460-467.
Hydrazoicacid, also known as hydrogen azide, azic acid or azoimide, is a compound with the chemical formula HN3. It is a colorless, volatile, and explosive...
and an incorrect order of acid addition for in situ formation of HNO2 will instead produce gaseous highly toxic hydrazoicacid (HN3). 2 NaN3 + 2 HNO2 →...
azide is produced by reaction of the carboxylic acid with hydrazoicacid via the protonated carboxylic acid, in a process akin to a Fischer esterification...
the formula N−3 and structure −N=N+=N−. It is the conjugate base of hydrazoicacid HN3. Organic azides are organic compounds with the formula RN3, containing...
carbon acids with nitroso compounds. The rearrangement of trityl N-haloamines in the Stieglitz rearrangement. By reaction of alkenes with hydrazoicacid in...
an inorganic azide with the formula Ba(N3)2. It is a barium salt of hydrazoicacid. Like most azides, it is explosive. It is less sensitive to mechanical...
phenyldiazonium. In the 1890s, Theodor Curtius, who had discovered hydrazoicacid (HN3), described the rearrangement of acyl azides to isocyanates subsequently...
it is a reagent in organic chemistry, serving as the equivalent of hydrazoicacid. Trimethylsilyl azide is commercially available. It may be prepared...
Lactams form by the acid-catalyzed rearrangement of oximes in the Beckmann rearrangement. Lactams form from cyclic ketones and hydrazoicacid in the Schmidt...
azide, Be(N3)2, is an inorganic compound. It is the beryllium analog of hydrazoicacid (HN3). Beryllium azide has been synthesised by the reaction of beryllium...
asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid (R−C(=O)−OH) with the hydroxyl group (−OH) replaced by an amine group (−NR′R″);...
chemical compound with the formula AgN3. It is a silver(I) salt of hydrazoicacid. It forms a colorless crystals. Like most azides, it is a primary explosive...
Curtius for the preparation of hydrazoicacid. Justus von Liebig showed in 1829 that hippuric acid differed from benzoic acid and he named it, and in 1834...
(1934–2003). In a typical protocol, one dissolves the alcohol, the carboxylic acid, and triphenylphosphine in tetrahydrofuran or other suitable solvent (e.g...
nonaromatic. 1H-Tetrazole was first prepared by the reaction of anhydrous hydrazoicacid and hydrogen cyanide under pressure. Treatment of organic nitriles with...
Lithium azide is the lithium salt of hydrazoicacid. It is an unstable and toxic compound that decomposes into lithium and nitrogen when heated. It can...
such as cyanogen; pseudohalide anions, such as cyanide ion; inorganic acids, such as hydrogen cyanide; as ligands in coordination complexes, such as...
the hydrazinium cation (N 2H+ 5) the product of nitrite reduction is hydrazoicacid (HN3), an instable and explosive compound: HNO2 + N 2H+ 5 → HN3 + H2O...
rearrangement in 1890/1894 and also discovered diazoacetic acid, hydrazine and hydrazoicacid.In 1882 he carried out the first ever peptide synthesis, creating...
sensitive explosive. It can be made by treating nickel carbonate with hydrazoicacid. Acetone causes the precipitation of the hydrous solid salt, which is...
Curtius, Th. (1890). "Ueber Stickstoffwasserstoffsäure (Azoimid) N3H" [On hydrazoicacid (azoimide) N3H]. Berichte der Deutschen Chemischen Gesellschaft zu Berlin...
chemical compound with the formula [NH4]N3, being the salt of ammonia and hydrazoicacid. Like other inorganic azides, this colourless crystalline salt is a...
being surpassed only by hydrazoicacid (97.7%). The production of N5[B(N3)4] requires a multi-step synthesis, first, hydrazoicacid and sodium borohydride...
standard sulfuric acid and the excess of acid then determined volumetrically; or the ammonia may be absorbed in hydrochloric acid and the ammonium chloride...
isocyanates: Schmidt reaction, a reaction where a carboxylic acid is treated with ammonia and hydrazoicacid yielding an isocyanate. Curtius rearrangement degradation...
azide would react with water vapour, rather than liquid water, to form hydrazoicacid, which could react with copper in the detonating cap to form copper...
solid that can be prepared by the protonolysis of diethylzinc with hydrazoicacid: Zn(C2H5)2 + 2 HN3 → Zn(N3)2 + 2 C2H6 Zinc azide is a coordination polymer...
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