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Preferred IUPAC name
Systematic IUPAC name
Other names
3D model (JSmol)
  • InChI=1S/H2N2O2/c3-1-2-4/h(H,1,4)(H,2,3)/p-2
  • (E): [O-]/N=N/[O-]
  • (Z): [O-]\N=N/[O-]
Molar mass  g·mol-1
Conjugate acid Hyponitrous acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

In chemistry, hyponitrite may refer to the anion ([ON=NO]2-), or to any ionic compound that contains it. In organic chemistry, it may also refer to the group -O-N=N-O-, or any organic compound with the generic formula R1-O-N=N-O-R2, where R1 and R2 are organic groups.[1] Such compounds can be viewed as salts and esters of respectively hyponitrous acid or HON=NOH.

An acid hyponitrite is an ionic compound with the anion ([HON=NO]-).

Hyponitrite ion

Hyponitrite exhibits cis-trans isomerism.[2]

The trans (E) form is generally found in hyponitrite salts such as sodium hyponitrite and silver(I) hyponitrite .

The cis (Z) form of sodium hyponitrite can be obtained too, and it is more reactive than the trans form.[2] The cis hyponitrite anion is nearly planar and almost symmetric, with lengths of about 140 pm for N-O bond and 120 pm for the N-N bond, and O-N-N angles of about 119°.[3]


The hyponitrite ions can act as a bidentate ligand in either bridging or chelating mode. There is a bridging cis-hyponitrite group in the red dinuclear form of nitrosyl pentammine cobalt(III) chloride, [Co(NH3)5NO]Cl2.[4]

Hyponitrite can act as a reducing agent for example reducing iodine:[4]

+ 3 + 3 -> + + 6 HI

Hyponitrite esters

Organic trans-hyponitrites R1-O-N=N-O-R2 can be obtained by reacting trans silver(I) hyponitrite with various alkyl halides. For example, reaction with t-butyl chloride yields trans di-tert-butyl hyponitrite.[5][6][7][8]

Other alkyl radicals reported in the literature include ethyl,[9] and benzyl.[10][11][12] These compounds can be a source of alkoxyl radicals.[13]

See also

Other nitrogen oxoanions include


  1. ^ M. N. Hughes (1968), "Hyponitrites". Quarterly Reviews of the Chemical Society, volume 22, issue 1, pages 1-13. doi:10.1039/QR9682200001.
  2. ^ a b Egon Wiberg, Arnold Frederick Holleman (2001) Inorganic Chemistry, Elsevier ISBN 0-12-352651-5
  3. ^ Claus Feldmann, Martin Jansen (1996), "cis-Sodium Hyponitrite - A New Preparative Route and a Crystal Structure Analysis". Angewandte Chemie International Edition in English, volume 35, issue 15, pages 1728-1730. doi:10.1002/anie.199617281.
  4. ^ a b Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
  5. ^ Navamoney Arulsamy; D. Scott Bohle; Jerome A. Imonigie; Elizabeth S. Sagan (2000). "Correlation of the Product E/Z Framework Geometry and O/O vs O/N Regioselectivity in the Dialkylation of Hyponitrite". J. Am. Chem. Soc. 122 (23): 5539-5549. doi:10.1021/ja994261o.
  6. ^ H. Kiefer and T. G. Traylor (1966), Tetrahedron Lett., page 6163.
  7. ^ R. L. Huang, T. W. Lee, and S. H. Ong (1969), J. Chem. Soc. C, page 40.
  8. ^ R. C. Neuman and R. J. Bussey (1970), J. Am. Chem. Soc., volume 92, page 2440.
  9. ^ J. R. Partington and C. C. Shah (1932), J. Chem. Soc., page 2589.
  10. ^ J. B. Sousa and S. K. Ho (1961), J. Chem. Soc., page 1788.
  11. ^ J. B. Sousa and S. K. Ho (1960), Nature, volume 186, page 776.
  12. ^ N. H. Ray (1960), J. Chem. Soc., page 4023.
  13. ^ Craig A. Ogle; Steven W. Martin; Michael P. Dziobak; Marek W. Urban; G. David Mendenhall (1983). "Decomposition rates, synthesis, and spectral properties of a series of alkyl hyponitrites". J. Org. Chem. 48 (21): 3728-3733. doi:10.1021/jo00169a023.

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