Hyponitrous acid

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Hyponitrous acid
Tautomer wireframe models of hyponitrous acid
Hyponitrous acid Ball and Stick (Tautomer 1).png
Hyponitrous acid Ball and Stick (Tautomer 2).png
Names
Preferred IUPAC name
Diazenediol
Systematic IUPAC name
N-(Hydroxyimino)hydroxylamine
Other names
Hyponitrous acid dimer
Identifiers
3D model (Jmol)
3DMet B00354
ChEBI
ChemSpider
141300
KEGG
Properties
H2N2O2
Molar mass 62.0282 g/mol
Appearance white crystals
Hazards
Main hazards explosive when dry
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Hyponitrous acid is a chemical compound with formula H
2
N
2
O
2
or HON=NOH. It is an isomer of nitramide, H2N−NO2.

Hyponitrous acid forms two series of salts, the hyponitrites containing the [ON=NO]2− anion, and the "acid hyponitrites" containing the [HON=NO] anion.[1]

Structure and properties[edit]

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) , and decomposes to nitrous oxide and water with a half life of 16 days at 25 °C at pH 1–3:

H
2
N
2
O
2
H
2
O
+ N
2
O

Since this reaction is not reversible, N
2
O
should not be considered as the anhydride of H
2
N
2
O
2
.[1]

The cis acid is not known,[1] but its sodium salt can be obtained.[2]

Preparation[edit]

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

Ag
2
N
2
O
2
+ 2 HCl → H
2
N
2
O
2
+ 2 AgCl

Spectroscopic data indicate a trans configuration for the resulting acid.[2]

Biological aspects[edit]

In enzymology, a hyponitrite reductase is an enzyme that catalyzes the chemical reaction[3]

H
2
N
2
O
2
+ 2 NADH + 2 H+
↔ 2 NH
2
OH
+ 2 NAD+

References[edit]

  1. ^ a b c Wiberg, Egon; Holleman, Arnold Frederick (2001). Inorganic Chemistry. Elsevier. ISBN 0-12-352651-5. 
  2. ^ a b 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. 
  3. ^ http://enzyme.expasy.org/EC/1.7.1.5