Silver hyponitrite

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Silver hyponitrite

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(Redirected from Silver(I) hyponitrite)

Silver hyponitrite
Names
Other names Silver(I) hyponitrite, Argentous hyponitrite
Identifiers
3D model (JSmol)	Interactive image
ChemSpider	66738928^Y
PubChem CID	129635977
CompTox Dashboard (EPA)	DTXSID701337128
InChI InChI=1S/2Ag.H2N2O2/c;;3-1-2-4/h;;(H,1,4)(H,2,3)/q2*+1;/p-2 Key: WFHLUHLBCCOOIU-UHFFFAOYSA-L
SMILES N(=N[O-])[O-].[Ag+].[Ag+]
Properties
Chemical formula	Ag₂N₂O₂
Molar mass	275.75
Appearance	bright canary yellow solid^[1]
Density	5.75 g/cm3 (at 30 °C)
Solubility in water	slightly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Silver hyponitrite is an ionic compound with formula Ag₂N₂O₂ or (Ag⁺
)₂[ON=NO]²⁻, containing monovalent silver cations and hyponitrite anions. It is a bright yellow solid practically insoluble in water and most organic solvents, including DMF and DMSO.^[1]^[2]^[3]

Preparation

[edit]

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

[edit]

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

[edit]

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

[edit]

Silver hyponitrite reacts with alkyl halides, to form alkyl hyponitrites. For example, reaction 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 ethyl,^[8] benzyl,^[9]^[10]^[11] and tert-butyl.^[12]^[13]^[14]

References

[edit]

^ ^a ^b ^c ^d Trambaklal Mohanlal Oza, Rajnikant Hariprasad Thaker (1955), "The Thermal Decomposition of Silver Hyponitrite". Journal of the American Chemical society, volume 77, issue 19, pages 4976–4980. doi:10.1021/ja01624a007
^ ^a ^b ^c ^d G. David Mendenhall (1974), "Convenient synthesis of silver hyponitrite". Journal of the American Chemical society, volume 96, issue 15, page 5000. doi:10.1021/ja00822a054
^ Wiberg, Egon; Holleman, Arnold Frederick (2001). Inorganic Chemistry. Elsevier. ISBN 0-12-352651-5.
^ (1848), "On the formation of hyponitrite of silver". Philosophical Magazine Series 3, XIII. Intelligence and miscellaneous articles, volume 33 (1848), issue 219, page 75. doi:10.1080/14786444808646049
^ ^a ^b Masatsugu Sekiguchi, Michio Kobayashi, Hiroshi Minato (1974), "Reactions between Acyl Halides and Silver Hyponitrite". Bulletin of the Chemical Society of Japan, volume 45, issue 9, pages 2932-2934. doi:10.1246/bcsj.45.2932
^ C.N. Polydoropoulos, Th. Yannakopoulos (1961), "Silver hyponitrite: Solubility product and complexes in aqueous ammonia". Journal of Inorganic and Nuclear Chemistry, volume 19, issues 1–2, pages 107–114. doi:10.1016/0022-1902(61)80053-5
^ 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.
^ J. R. Partington and C. C. Shah (1932), J. Chem. Soc., page 2589.
^ Ho, S. K.; de Sousa, J. B. (1961). "347. Alkoxy-radicals. Part I. The kinetics of thermal decomposition of dibenzyl hyponitrite in solution". Journal of the Chemical Society (Resumed): 1788. doi:10.1039/JR9610001788.
^ J. B. Sousa and S. K. Ho (1960), Nature, volume 186, page 776.
^ Ray, N. H. (1 January 1960). "794. The rates of decomposition of free-radical polymerisation-catalysts: measurements of short half-lives by a thermal method". Journal of the Chemical Society (Resumed): 4023–4028. doi:10.1039/JR9600004023.
^ H. Kiefer and T. G. Traylor (1966), Tetrahedron Lett., page 6163.
^ Huang, R. L.; Lee, Tong-Wai; Ong, S. H. (1 January 1969). "Reactions of the α-methoxybenzyl radical in carbon tetrachloride and in other solvents. Carbon tetrachloride as a chlorinating agent". Journal of the Chemical Society C: Organic (1): 40–44. doi:10.1039/J39690000040.
^ R. C. Neuman and R. J. Bussey (1970), J. Am. Chem. Soc., volume 92, page 2440.

Silver compounds

Silver(0,I)

Ag₂F

Silver(I)

Organosilver(I) compounds	AgC₂H₃O₂ AgC₂₂H₄₃O₂ CH₃CH(OH)COOAg C ₁₈H ₃₆AgO ₂ AgC₄H₃N₂NSO₂C₆H₄NH₂ AgC ₁₁H ₂₃COO

Silver(II)

Silver(III)

Silver(I,III)

Ag₄O₄

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