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Hyponitrous acid

From Wikipedia, the free encyclopedia
Hyponitrous acid
Tautomer wireframe models of hyponitrous acid
Tautomer wireframe models of hyponitrous acid
Names
Preferred IUPAC name
Diazenediol
Systematic IUPAC name
N-(Hydroxyimino)hydroxylamine
Other names
Hyponitrous acid dimer
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
141300
KEGG
  • InChI=1S/H2N2O/c3-1-2-4/h(H,1,4)(H,2,3)
    Key: NFMHSPWHNQRFNR-UHFFFAOYSA-N
  • ON=NO
Properties
H2N2O2
Molar mass62.0282 g/mol
Appearancewhite crystals
Conjugate baseHyponitrite
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
explosive when dry
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Hyponitrous acid is a chemical compound with formulaH
2N
2O
2 or HON=NOH. It is an isomer ofnitramide, H2N−NO2, and a formal dimer ofazanone, HNO.

Hyponitrous acid forms two series ofsalts, thehyponitrites 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 andcis.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 tonitrous 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,N
2O should not be considered as the anhydride ofH
2N
2O
2.[1]

Thecis acid is not known,[1] but itssodium salt can be obtained.[3]

Preparation

[edit]

Hyponitrous acid (trans) can be prepared fromsilver(I) hyponitrite and anhydrousHCl inether:

Ag2N2O2 + 2 HCl → H2N2O2 + 2 AgCl

Spectroscopic data indicate atrans configuration for the resulting acid.[3]

It can also be synthesized fromhydroxylamine andnitrous acid:

NH2OH + HNO2 → H2N2O2 + H2O

Biological aspects

[edit]

Inenzymology, ahyponitrite reductase is anenzyme thatcatalyzes thechemical reaction:[4]

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

References

[edit]
  1. ^abcWiberg, Egon; Holleman, Arnold Frederick (2001).Inorganic Chemistry. Elsevier.ISBN 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.
  3. ^abCatherine 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.
  4. ^"ENZYME - 1.7.1.5 Hyponitrite reductase".
Nitrogen species
Hydrides
Organic
Oxides
Halides
Oxidation states
−3,−2,−1, 0,+1,+2,+3,+4,+5 (a stronglyacidic oxide)
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