Silver hyponitrite

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Silver(I) hyponitrite
)
Silver hyponitrite
Names
Other names
Silver(I) hyponitrite, Argentous hyponitrite
Identifiers
3D model (
JSmol
)
ChemSpider
  • InChI=1S/2Ag.H2N2O2/c;;3-1-2-4/h;;(H,1,4)(H,2,3)/q2*+1;/p-2
    Key: WFHLUHLBCCOOIU-UHFFFAOYSA-L
  • N(=N[O-])[O-].[Ag+].[Ag+]
Properties
Ag2N2O2
Molar mass 275.75
Appearance bright canary yellow solid[1]
Density 5.75 g/cm3 (at 30 °C)
slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Silver hyponitrite is an

anions. It is a bright yellow solid practically insoluble in water and most organic solvents, including DMF and DMSO.[1][2][3]

Preparation

The compound was described in 1848.[4]

The salt can be precipitated from a solution of sodium hyponitrite in water by the addition of silver nitrate:[2]

Na
2N
2O
2 + 2 AgNO
3 → Ag
2N
2O
2 + 2 NaNO
3

Excess silver nitrate yields a brown or black precipitate.[1][2]

Silver hyponitrite can also be prepared by reacting silver nitrate with sodium amalgam.[5]

Properties and reactions

Silver hyponitrite is sparingly soluble in concentrated alkali hyponitrite solutions, but quite soluble in aqueous ammonia due to the formation of the complex cation [(NH
3)2Ag]+.[6] The compound is slowly decomposed by light.[5]

The anhydrous compound decomposes in vacuum at 158 °C. The primary decomposition products are

silver(I) oxide Ag
2O and nitrous oxide N
2O. However, these then react to form a variable mixture of nitrogen, metallic silver, and various oxides of the two elements and silver salts.[1]

Hyponitrous acid

Reaction of silver hyponitrite with anhydrous hydrogen chloride in ether is the standard way to prepare hyponitrous acid:

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

Spectroscopic data indicate a trans configuration for the resulting acid.[7]

Alkyl halides

Silver hyponitrite reacts with

methyl bromide yields the spontaneously explosive dimethyl hyponitrite:[2]

2 CH
3Br + Ag
2N
2O
2 → H
3C-O-N=N-O-CH
3 + 2 AgBr

Other alkyl hyponitrites reported in the literature include those of

tert-butyl.[12][13][14]

References

  1. ^
    doi:10.1021/ja01624a007
  2. ^
    doi:10.1021/ja00822a054
  3. ISBN 0-12-352651-5
    .
  4. doi:10.1080/14786444808646049
  5. ^
    doi:10.1246/bcsj.45.2932
  6. doi:10.1016/0022-1902(61)80053-5
  7. ISBN 978-0-13-175553-6
    .
  8. ^ J. R. Partington and C. C. Shah (1932), J. Chem. Soc., page 2589.
  9. doi:10.1039/JR9610001788
    .
  10. ^ J. B. Sousa and S. K. Ho (1960), Nature, volume 186, page 776.
  11. doi:10.1039/JR9600004023
    .
  12. ^ H. Kiefer and T. G. Traylor (1966), Tetrahedron Lett., page 6163.
  13. doi:10.1039/J39690000040
    .
  14. ^ R. C. Neuman and R. J. Bussey (1970), J. Am. Chem. Soc., volume 92, page 2440.
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