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Hyponitrous acid
Chemical compound

Hyponitrous acid is a chemical compound with formula H2N2O2 or HON=NOH. It is an isomer of nitramide, H2N−NO2, and a formal dimer of azanone, HNO.

Hyponitrous acid forms two series of salts, the hyponitrites containing the [ON=NO]2− anion and the "acid hyponitrites" containing the [HON=NO]− anion.

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Structure and properties

There are two possible structures of hyponitrous acid, trans and cis. trans-Hyponitrous acid forms white crystals that are explosive when dry. In aqueous solution, it is a weak acid (pKa1 = 7.21, pKa2 = 11.54),2 and decomposes to nitrous oxide and water with a half life of 16 days at 25 °C at pH 1–3:

H2N2O2 → H2O + N2O

Since this reaction is not reversible, N2O should not be considered as the anhydride of H2N2O2.3

The cis acid is not known,4 but its sodium salt can be obtained.5

Preparation

Hyponitrous acid (trans) can be prepared from silver(I) hyponitrite and anhydrous HCl in ether:

Ag2N2O2 + 2 HCl → H2N2O2 + 2 AgCl

Spectroscopic data indicate a trans configuration for the resulting acid.6

It can also be synthesized from hydroxylamine and nitrous acid:

NH2OH + HNO2 → H2N2O2 + H2O

Biological aspects

In enzymology, a hyponitrite reductase is an enzyme that catalyzes the chemical reaction:7

H2N2O2 + 2 NADH + 2 H+ ⇌ 2 NH2OH + 2 NAD+

References

  1. Wiberg, Egon; Holleman, Arnold Frederick (2001). Inorganic Chemistry. Elsevier. ISBN 0-12-352651-5. 0-12-352651-5

  2. 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 120. ISBN 0-08-029214-3. LCCN 82-16524. 0-08-029214-3

  3. Wiberg, Egon; Holleman, Arnold Frederick (2001). Inorganic Chemistry. Elsevier. ISBN 0-12-352651-5. 0-12-352651-5

  4. Wiberg, Egon; Holleman, Arnold Frederick (2001). Inorganic Chemistry. Elsevier. ISBN 0-12-352651-5. 0-12-352651-5

  5. Catherine E. Housecroft; Alan G. Sharpe (2008). "Chapter 15: The group 15 elements". Inorganic Chemistry (3rd ed.). Pearson. p. 468. ISBN 978-0-13-175553-6. 978-0-13-175553-6

  6. Catherine E. Housecroft; Alan G. Sharpe (2008). "Chapter 15: The group 15 elements". Inorganic Chemistry (3rd ed.). Pearson. p. 468. ISBN 978-0-13-175553-6. 978-0-13-175553-6

  7. "ENZYME - 1.7.1.5 Hyponitrite reductase". http://enzyme.expasy.org/EC/1.7.1.5