Silver hyponitrite is an

ionic compound In chemistry, an ionic compound is a chemical compound composed of ions held together by electrostatic forces termed ionic bonding. The compound is neutral overall, but consists of positively charged ions called cations and negatively charged i ...

with formula Ag₂N₂O₂ or ()₂ N=NOsup>2−, containing monovalent

silver Silver is a chemical element with the Symbol (chemistry), symbol Ag (from the Latin ', derived from the Proto-Indo-European wikt:Reconstruction:Proto-Indo-European/h₂erǵ-, ''h₂erǵ'': "shiny" or "white") and atomic number 47. A soft, whi ...

cation An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

s and

hyponitrite In chemistry, hyponitrite may refer to the anion ( N=NOsup>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� ...

anion An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convent ...

s. It is a bright canary yellow solid practically insoluble in water and most organic solvents, including DMF and

DMSO Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula ( CH3)2. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds an ...

.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. G. David Mendenhall (1974), "Convenient synthesis of silver hyponitrite". Journal of the American Chemical society, volume 96, issue 15, page 5000.

Preparation

The compound was described in 1848.(1848), "On the formation of hyponitrite of silver". Philosophical Magazine Series 3, XIII. Intelligence and miscellaneous articles, volume 33 (1848), issue 219, page 75. The salt can be precipitated from a solution of

sodium hyponitrite Sodium hyponitrite is a solid ionic compound with formula or ()2 N=NO−.Egon Wiberg, Arnold Frederick Holleman (2001) ''Inorganic Chemistry'', Elsevier There are ''cis'' and ''trans'' forms of the hyponitrite ion . The ''trans'' form is mo ...

in water by the addition of

silver nitrate Silver nitrate is an inorganic compound with chemical formula . It is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides. It was once called ''lunar caustic' ...

: : + 2 → + 2 Excess silver nitrate yields a brown or black precipitate. Silver hyponitrite can be prepared also by reducing silver nitrate with

sodium amalgam Sodium amalgam, commonly denoted Na(Hg), is an alloy of mercury and sodium. The term amalgam is used for alloys, intermetallic compounds, and solutions (both solid solutions and liquid solutions) involving mercury as a major component. Sodium amal ...

Properties and reactions

Silver hyponitrite is sparingly soluble in concentrated

alkali In chemistry, an alkali (; from ar, القلوي, al-qaly, lit=ashes of the saltwort) is a basic, ionic salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as a base that dissolves in water. A solution of a ...

hyponitrite solutions, but quite soluble in aqueous

ammonia Ammonia is an inorganic compound of nitrogen and hydrogen with the formula . A stable binary hydride, and the simplest pnictogen hydride, ammonia is a colourless gas with a distinct pungent smell. Biologically, it is a common nitrogenous was ...

due to the formation of the complex cation )₂Agsup>+.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. The compound is slowly decomposed by light.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. The anhydrous compound decomposes in vacuum at 158 °C. The primary decomposition products are

silver(I) oxide Silver oxide is the chemical compound with the formula Ag2O. It is a fine black or dark brown powder that is used to prepare other silver compounds. Preparation Silver oxide can be prepared by combining aqueous solutions of silver nitrate and a ...

and

nitrous oxide Nitrous oxide (dinitrogen oxide or dinitrogen monoxide), commonly known as laughing gas, nitrous, or nos, is a chemical compound, an oxide of nitrogen with the formula . At room temperature, it is a colourless non-flammable gas, and has a ...

. However, these then react to form a variable mixture of

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

, metallic

, and various

oxide An oxide () is a chemical compound that contains at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– (molecular) ion. with oxygen in the oxidation state of −2. Most of the E ...

s of the two elements and silver salts.

Hyponitrous acid

Reaction of silver hyponitrite with anhydrous

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

is the standard way to prepare

hyponitrous acid Hyponitrous acid is a chemical compound with formula or HON=NOH. It is an isomer of nitramide, H2N−NO2; and a formal dimer of azanone, HNO. Hyponitrous acid forms two series of salts, the hyponitrites containing the N=NOsup>2− anion, and th ...

: : + 2 HCl → + 2 AgCl Spectroscopic data indicate a ''trans'' configuration for the resulting acid.

Alkyl halides

Silver hyponitrite reacts with

alkyl halides The haloalkanes (also known as halogenoalkanes or alkyl halides) are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely us ...

, to form alkyl hyponitrites. For example, reaction with

methyl bromide Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula C H3 Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozon ...

yields the spontaneously explosive liquid dimethyl hyponitrite: : 2 + → -O-N=N-O- + 2 AgBr Other alkyl hyponitrites reported in the literature include those of

ethyl Ethyl may refer to: Arts and entertainment * Cold Ethyl, a Swedish rock band *Ethyl Sinclair, a character in the ''Dinosaurs'' television show Science and technology * Ethyl group, an organic chemistry moiety * Ethyl alcohol (or ethanol) * E ...

,J. R. Partington and C. C. Shah (1932), J. Chem. Soc., page 2589.

benzyl In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure . Benzyl features a benzene ring () attached to a methylene group () group. Nomenclature In IUPAC nomenclature, the prefix benzyl refers to a substi ...

,J. B. Sousa and S. K. Ho (1960), Nature, volume 186, page 776. and ''tert''-butyl.H. Kiefer and T. G. Traylor (1966), Tetrahedron Lett., page 6163.R. C. Neuman and R. J. Bussey (1970), J. Am. Chem. Soc., volume 92, page 2440.

References

{{Silver compounds Silver compounds Nitrogen–oxygen compounds