Silver hyponitrite is an

ionic compound In chemistry, a salt or ionic compound is a chemical compound consisting of an assembly of positively charged ions (Cation, cations) and negatively charged ions (Anion, anions), which results in a compound with no net electric charge (electrica ...

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

silver Silver is a chemical element; it has Symbol (chemistry), symbol Ag () and atomic number 47. A soft, whitish-gray, lustrous transition metal, it exhibits the highest electrical conductivity, thermal conductivity, and reflectivity of any metal. ...

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

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 conven ...

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

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

.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 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 causti ...

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

with

sodium amalgam Sodium amalgam, with the common formula 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. ...

Properties and reactions

Silver hyponitrite is sparingly soluble in concentrated

alkali In chemistry, an alkali (; from the Arabic word , ) is a basic 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 soluble base has a pH greater than 7.0. The a ...

hyponitrite solutions, but quite soluble in aqueous

ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...

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 and

nitrous oxide Nitrous oxide (dinitrogen oxide or dinitrogen monoxide), commonly known as laughing gas, nitrous, or factitious air, among others, is a chemical compound, an Nitrogen oxide, oxide of nitrogen with the Chemical formula, formula . At room te ...

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

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

, metallic

, and various

oxide An oxide () is a chemical compound containing at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion (anion bearing a net charge of −2) of oxygen, an O2− ion with oxygen in the oxidation st ...

s of the two elements and silver salts.

Hyponitrous acid

Reaction of silver hyponitrite with anhydrous

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

ether In organic chemistry, ethers are a class of compounds that contain an ether group, a single oxygen atom bonded to two separate carbon atoms, each part of an organyl group (e.g., alkyl or aryl). They have the general formula , where R and R� ...

is the standard way to prepare hyponitrous acid: : + 2 HCl → + 2 AgCl Spectroscopic data indicate a ''trans'' configuration for the resulting acid.

Alkyl halides

Silver hyponitrite reacts with alkyl halides, to form alkyl hyponitrites. For example, reaction with

methyl bromide Bromomethane, commonly known as methyl bromide, is an organobromine compound with chemical formula, formula Carbon, CHydrogen, H3Bromine, Br. This colorless, odorless, nonflammable gas is Bromine cycle, produced both industrially and biologically ...

yields the spontaneously explosive dimethyl hyponitrite: : 2 + → -O-N=N-O- + 2 AgBr Other alkyl hyponitrites reported in the literature include those of ethyl,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 (). Nomenclature In IUPAC nomenclature, the prefix benzyl refers to a substituent ...

,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 Hyponitrites