Silver carbonate

Silver carbonate is the chemical compound with the formula Ag2CO3. Silver carbonate is yellow but typical samples are grayish due to the presence of elemental silver. It is poorly soluble in water, like most transition metal carbonates.

Silver carbonate
Crystal structure of silver carbonate
Sample of microcrystaline silver carbonate
Names
IUPAC name
Silver(I) carbonate, Silver carbonate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.811
EC Number
  • 208-590-3
MeSH silver+carbonate
UNII
Properties
Ag2CO3
Molar mass 275.75 g/mol
Appearance Pale yellow crystals
Odor Odorless
Density 6.077 g/cm3[1]
Melting point 218 °C (424 °F; 491 K)
decomposes from 120 °C[1][4]
0.031 g/L (15 °C)
0.032 g/L (25 °C)
0.5 g/L (100 °C)[2]
8.46·10−12[1]
Solubility Insoluble in alcohol, liquid ammonia, acetates, acetone[3]
−80.9·10−6 cm3/mol[1]
Structure
Monoclinic, mP12 (295 K)
Trigonal, hP36 (β-form, 453 K)
Hexagonal, hP18 (α-form, 476 K)[5]
P21/m, No. 11 (295 K)
P31c, No. 159 (β-form, 453 K)
P62m, No. 189 (α-form, 476 K)[5]
2/m (295 K)
3m (β-form, 453 K)
6m2 (α-form, 476 K)[5]
a = 4.8521(2) Å, b = 9.5489(4) Å, c = 3.2536(1) Å (295 K)[5]
α = 90°, β = 91.9713(3)°, γ = 90°
Thermochemistry
112.3 J/mol·K[1]
167.4 J/mol·K[1]
−505.8 kJ/mol[1]
−436.8 kJ/mol[1][4]
Hazards
GHS pictograms GHS07: Harmful[6]
GHS signal word Warning
H315, H319, H335[6]
P261, P305+351+338[6]
Inhalation hazard Irritant
NFPA 704
Lethal dose or concentration (LD, LC):
3.73 g/kg (mice, oral)[7]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Preparation and reactions

Silver carbonate can be prepared by combining aqueous solutions of sodium carbonate with a deficiency of silver nitrate.[8]

2 AgNO3(aq) + Na2CO3(aq) → Ag2CO3(s) + 2 NaNO3(aq)

Freshly prepared silver carbonate is colourless, but the solid quickly turns yellow.[9]

Silver carbonate reacts with ammonia to give the explosive fulminating silver. With hydrofluoric acid, it gives silver fluoride. The thermal conversion of silver carbonate to silver metal proceeds via formation of silver oxide:[10]

Ag2CO3 → Ag2O + CO2
2Ag2O → 4 Ag + O2

Uses

The principal use of silver carbonate is for the production of silver powder for use in microelectronics. It is reduced with formaldehyde, producing silver free of alkali metals:[9]

Ag2CO3 + CH2O → 2 Ag + 2 CO2 + H2

Silver carbonate is used as a reagent in organic synthesis such as the Koenigs-Knorr reaction. In the Fétizon oxidation, silver carbonate on celite serves as an oxidising agent to form lactones from diols. It is also employed to convert alkyl bromides into alcohols.[8] As a base, it has been used in the Wittig reaction.[11] and in C-H bond activation .[12]

References

  1. ^ a b c d e f g h Lide, David R., ed. (2009). CRC Handbook of Chemistry and Physics (90th ed.). Boca Raton, Florida: CRC Press. ISBN 978-1-4200-9084-0.
  2. ^ Seidell, Atherton; Linke, William F. (1919). Solubilities of Inorganic and Organic Compounds (2nd ed.). New York City: D. Van Nostrand Company. p. 605.
  3. ^ Comey, Arthur Messinger; Hahn, Dorothy A. (February 1921). A Dictionary of Chemical Solubilities: Inorganic (2nd ed.). New York: The MacMillan Company. p. 203.
  4. ^ a b Anatolievich, Kiper Ruslan. "silver nitrate". http://chemister.ru. Retrieved 2014-07-21. External link in |website= (help)
  5. ^ a b c d Norby, P.; Dinnebier, R.; Fitch, A.N. (2002). "Decomposition of Silver Carbonate; the Crystal Structure of Two High-Temperature Modifications of Ag2CO3". Inorganic Chemistry. 41 (14). doi:10.1021/ic0111177.
  6. ^ a b c Sigma-Aldrich Co., Silver carbonate. Retrieved on 2014-05-06.
  7. ^ a b "Silver Carbonate MSDS". http://www.saltlakemetals.com. Salt Lake City, Utah: Salt Lake Metals. Retrieved 2014-06-08. External link in |website= (help)
  8. ^ a b McCloskey C. M.; Coleman, G. H. (1955). "β-d-Glucose-2,3,4,6-Tetraacetate". Organic Syntheses.; Collective Volume, 3, p. 434
  9. ^ a b Andreas Brumby et al. "Silver, Silver Compounds, and Silver Alloys" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2008. doi:10.1002/14356007.a24_107.pub2
  10. ^ Koga, Nobuyoshi; Shuto Yamada; Tomoyasu Kimura (2013). "Thermal Decomposition of Silver Carbonate: Phenomenology and Physicogeometrical Kinetics". The Journal of Physical Chemistry C. 117: 326–336. doi:10.1021/jp309655s.
  11. ^ Jedinak, Lukas et al. “Use of Silver Carbonate in the Wittig Reaction.” The Journal of Organic Chemistry 78.23 (2013): 12224–12228.
  12. ^ J. Org. Chem., 2018, 83 (16), pp 9312–9321 DOI: 10.1021/acs.joc.8b01284. .

External links

Carbonates
H2CO3 He
Li2CO3,
LiHCO3
BeCO3 B C (NH4)2CO3,
NH4HCO3
O F Ne
Na2CO3,
NaHCO3,
Na3H(CO3)2
MgCO3,
Mg(HCO3)2
Al2(CO3)3 Si P S Cl Ar
K2CO3,
KHCO3
CaCO3,
Ca(HCO3)2
Sc Ti V Cr MnCO3 FeCO3 CoCO3 NiCO3 CuCO3 ZnCO3 Ga Ge As Se Br Kr
Rb2CO3 SrCO3 Y Zr Nb Mo Tc Ru Rh Pd Ag2CO3 CdCO3 In Sn Sb Te I Xe
Cs2CO3,
CsHCO3
BaCO3   Hf Ta W Re Os Ir Pt Au Hg Tl2CO3 PbCO3 (BiO)2CO3 Po At Rn
Fr Ra   Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc Lv Ts Og
La2(CO3)3 Ce2(CO3)3 Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
Ac Th Pa UO2CO3 Np Pu Am Cm Bk Cf Es Fm Md No Lr
Carl Wilhelm Scheele

Carl Wilhelm Scheele (German: [ˈʃeːlə], Swedish: [²ɧeːlɛ]; 9 December 1742 – 21 May 1786) was a Swedish Pomeranian and German pharmaceutical chemist. Isaac Asimov called him "hard-luck Scheele" because he made a number of chemical discoveries before others who are generally given the credit. For example, Scheele discovered oxygen (although Joseph Priestley published his findings first), and identified molybdenum, tungsten, barium, hydrogen, and chlorine before Humphry Davy, among others. Scheele discovered organic acids tartaric, oxalic, uric, lactic, and citric, as well as hydrofluoric, hydrocyanic, and arsenic acids. He preferred speaking German to Swedish his whole life, as German was commonly spoken among Swedish pharmacists.

Decarboxylative cross-coupling

Decarboxylative cross coupling reactions are chemical reactions in which a carboxylic acid is reacted with an organic halide to form a new carbon-carbon bond, concomitant with loss of CO2. Aryl and alkyl halides participate. Metal catalyst, base, and oxidant are required.

A significant advantage of this reaction is that it uses relatively inexpensive carboxylic acids (or their salts) and is far less air and moisture sensitive in comparison to typical cross-coupling organometallic reagents. Furthermore, the carboxylic acid moiety is a common feature of natural products and can also be prepared by relatively benign air oxidations. Additional benefits include the broad tolerance of functional groups, as well as the capacity to avoid the use of strong bases. An important elementary step in this reaction is protodecarboxylation or metalation to first convert the C–COOH bond to a C–H or C–M bond respectively.

Fétizon oxidation

Fétizon oxidation is the oxidation of primary and secondary alcohols utilizing the compound silver(I) carbonate absorbed onto the surface of celite also known as Fétizon's reagent first employed by Marcel Fétizon in 1968. It is a mild reagent, suitable for both acid and base sensitive compounds. Its great reactivity with lactols makes the Fétizon oxidation a useful method to obtain lactones from a diol. The reaction is inhibited significantly by polar groups within the reaction system as well as steric hindrance of the α-hydrogen of the alcohol.

Glycoside

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

In formal terms, a glycoside is any molecule in which a sugar group is bonded through its anomeric carbon to another group via a glycosidic bond. Glycosides can be linked by an O- (an O-glycoside), N- (a glycosylamine), S-(a thioglycoside), or C- (a C-glycoside) glycosidic bond. According to the IUPAC, the name "C-glycoside" is a misnomer; the preferred term is "C-glycosyl compound". The given definition is the one used by IUPAC, which recommends the Haworth projection to correctly assign stereochemical configurations. Many authors require in addition that the sugar be bonded to a non-sugar for the molecule to qualify as a glycoside, thus excluding polysaccharides. The sugar group is then known as the glycone and the non-sugar group as the aglycone or genin part of the glycoside. The glycone can consist of a single sugar group (monosaccharide) or several sugar groups (oligosaccharide).

The first glycoside ever identified was amygdalin, by the French chemists Pierre Robiquet and Antoine Boutron-Charlard, in 1830.

Joseph Bancroft Reade

Rev. Joseph Bancroft Reade FRS FRMS (5 April 1801 – 12 December 1870) was an English clergyman, amateur scientist and pioneer of photography.

Koenigs–Knorr reaction

The Koenigs–Knorr reaction in organic chemistry is the substitution reaction of a glycosyl halide with an alcohol to give a glycoside. It is one of the oldest and simplest glycosylation reactions. It is named after Wilhelm Koenigs (1851–1906), a student of von Bayer and fellow student with Hermann Emil Fischer, and Edward Knorr, a student of Koenigs.

In its original form, Koenigs and Knorr treated acetobromoglucose with alcohols in the presence of silver carbonate. Shortly afterwards Fischer and Armstrong reported very similar findings.In the above example, the stereochemical outcome is determined by the presence of the neighboring group at C2 that lends anchimeric assistance, resulting in the formation of a 1,2-trans stereochemical arrangement. Esters (e.g. acetyl, benzoyl, pivalyl) generally provide good anchimeric assistance, whereas ethers (e.g. benzyl, methyl etc.) do not, leading to mixtures of stereoisomers.

List of CAS numbers by chemical compound

This is a list of CAS numbers by chemical formulas and chemical compounds, indexed by formula. This complements alternative listings to be found at list of inorganic compounds, list of organic compounds and inorganic compounds by element.

Oxidation of secondary alcohols to ketones

The oxidation of secondary alcohols to ketones is an important oxidation reaction in organic chemistry.

Where a secondary alcohol is oxidised, it is converted to a ketone. The hydrogen from the hydroxyl group is lost along with the hydrogen bonded to the second carbon. The remaining oxygen then forms double bonds with the carbon. This leaves a ketone, as R1–COR2. Ketones cannot normally be oxidised any further because this would involve breaking a C–C bond, which requires too much energy.The reaction can occur using a variety of oxidants.

Pío del Río Hortega

Pío del Río Hortega (1882 – 1945) was a Spanish neuroscientist who discovered microglia.

Silver

Silver is a chemical element with the symbol Ag (from the Latin argentum, derived from the Proto-Indo-European h₂erǵ: "shiny" or "white") and atomic number 47. A soft, white, lustrous transition metal, it exhibits the highest electrical conductivity, thermal conductivity, and reflectivity of any metal. The metal is found in the Earth's crust in the pure, free elemental form ("native silver"), as an alloy with gold and other metals, and in minerals such as argentite and chlorargyrite. Most silver is produced as a byproduct of copper, gold, lead, and zinc refining.

Silver has long been valued as a precious metal. Silver metal is used in many bullion coins, sometimes alongside gold: while it is more abundant than gold, it is much less abundant as a native metal. Its purity is typically measured on a per-mille basis; a 94%-pure alloy is described as "0.940 fine". As one of the seven metals of antiquity, silver has had an enduring role in most human cultures.

Other than in currency and as an investment medium (coins and bullion), silver is used in solar panels, water filtration, jewellery, ornaments, high-value tableware and utensils (hence the term silverware), in electrical contacts and conductors, in specialized mirrors, window coatings, in catalysis of chemical reactions, as a colorant in stained glass and in specialised confectionery. Its compounds are used in photographic and X-ray film. Dilute solutions of silver nitrate and other silver compounds are used as disinfectants and microbiocides (oligodynamic effect), added to bandages and wound-dressings, catheters, and other medical instruments.

Silver(I) fluoride

Silver(I) fluoride is the inorganic compound with the formula AgF. It is one of the three main fluorides of silver, the others being silver subfluoride and silver(II) fluoride. AgF has relatively few niche applications; it has been employed as a fluorination and desilylation reagent in organic synthesis and in aqueous solution as a topical caries treatment in dentistry.

The hydrates of AgF present as colourless, while pure anhydrous samples are yellow.

Silver acetate

Silver acetate is an inorganic compound with the empirical formula CH3CO2Ag (or AgC2H3O2). It is a photosensitive, white, crystalline solid. It is a useful reagent in the laboratory as a source of silver ions lacking an oxidizing anion. It has been used in some antismoking drugs.

Silver fulminate

Silver fulminate (AgCNO) is the highly explosive silver salt of fulminic acid.

Silver fulminate is a primary explosive, but has limited use as such due to its extreme sensitivity to impact, heat, pressure and electricity. The compound becomes progressively sensitive as it is aggregated, even in small amounts; the touch of a falling feather, the impact of a single water droplet or a small static discharge are all capable of explosively detonating an unconfined pile of silver fulminate no larger than a dime and no heavier than a few milligrams. Aggregating larger quantities is impossible due to the compound's tendency to self-detonate under its own weight.

Silver fulminate was first prepared in 1800 by Edward Charles Howard in his research project to prepare a large variety of fulminates. Along with mercury fulminate, it is the only fulminate stable enough for commercial use. Detonators using silver fulminate were used to initiate picric acid in 1885, but since have only been used by the Italian navy. The current commercial use has been in producing non-damaging novelty noisemakers as children's toys and tricks.

Silver nitrate

Silver nitrate is an inorganic compound with chemical formula AgNO3. This compound 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 because silver was called luna by the ancient alchemists, who believed that silver was associated with the moon.In solid silver nitrate, the silver ions are three-coordinated in a trigonal planar arrangement.

Silver sulfite

Silver sulfite is the chemical compound with the formula Ag2SO3. This unstable silver compound when heated and/or in light it decomposes to silver dithionate and silver sulfate.

Silver trifluoromethanesulfonate

Silver trifluoromethanesulfonate, or silver triflate is the triflate (CF3SO3−) salt of Ag+. It is a white or colorless solid that is soluble in water and some organic solvents (most interestingly, benzene). It is a reagent in the synthesis of organic and inorganic triflates.

Solubility table

The table below provides information on the variation of solubility of different substances (mostly inorganic compounds) in water with temperature, at 1 atmosphere pressure. Units of solubility are given in grams per 100 millilitres of water (g/100 ml), unless shown otherwise. The substances are listed in alphabetical order.

Sulfolene

Sulfolene, or butadiene sulfone is a cyclic organic chemical with a sulfone functional group. It is a white, odorless, crystalline, indefinitely storable solid, which dissolves in water and many organic solvents. The compound is used as a source of butadiene.

Vinyl iodide functional group

In organic chemistry, a vinyl iodide functional group (also known as iodoalkenes) is any alkene with an iodide substituent directly bonded to one of the alkene carbons (sp2). Vinyl iodides are versatile molecules that serve as important building blocks and precursors in organic synthesis. They are commonly used in carbon-carbon forming reactions in transition-metal catalyzed cross-coupling reactions, such as Heck reaction, Sonogashira coupling, and Suzuki coupling. Synthesis of well-defined geometry or complexity vinyl iodide is important in stereoselective synthesis of natural products and drugs.

Silver compounds
Silver(0,I)
Silver(I)
Silver(II)
Silver(III)
Silver(I,III)

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