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Silver Triflate
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 including, benzene. It is a reagent used in the synthesis of organic and inorganic triflates. Synthesis An early preparation method starts from the barium salt of trifluoromethanesulfonic acid (TfOH), from which the free TfOH is formed with dilute sulfuric acid, which is then neutralized with silver carbonate (Ag2CO3). :Ba^2+ SO2CF3 -> ce-\ce] CF3SO2OH -> ceCF3SO2O^- Ag+ The silver triflate is thereby obtained in a yield of 95% and can be recrystallized from benzene/tetrachloromethane or ether/tetrachloromethane for purification. In an improved version by George Whitesides, dilute TfOH is reacted with silver(I)oxide (Ag2O), which produces AgOTf in 98% yield. Reactions It is used to prepare alkyl triflates from alkyl halides: :CF3SO2OAg + RX → CF3SO2OR + AgX (X = iodide usually) In coordination ...
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Triflate
In organic chemistry, triflate (Preferred IUPAC name, systematic name: trifluoromethanesulfonate), is a functional group with the Chemical formula, formula and Chemical structure, structure . The triflate group is often represented by , as opposed to −Tf, which is the trifluoromethylsulfonyl, triflyl group, . For example, Butyl group, ''n''-butyl triflate can be written as . The corresponding triflate Ion, anion, , is an extremely stable polyatomic ion; this comes from the fact that triflic acid () is a superacid; i.e. it is more acidic than pure sulfuric acid, already one of the strongest acids known. Applications A triflate group is an excellent leaving group used in certain organic reactions such as nucleophilic substitution, Suzuki couplings and Heck reactions. Since alkyl triflates are extremely reactive in SN2 reaction, SN2 reactions, they must be stored in conditions free of nucleophiles (such as water). The anion owes its stability to resonance stabilization which ca ...
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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. Silver is found in the Earth's crust in the pure, free elemental form ("native metal, 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 (metallurgy), refining. Silver has long been valued as a precious metal. Silver metal is used in many bullion coins, sometimes bimetallism, 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 in ...
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Benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon. Benzene is a natural constituent of petroleum and is one of the elementary petrochemicals. Due to the cyclic continuous pi bonds between the carbon atoms, benzene is classed as an aromatic hydrocarbon. Benzene is a colorless and highly Combustibility and flammability, flammable liquid with a sweet smell, and is partially responsible for the aroma of gasoline. It is used primarily as a Precursor (chemistry), precursor to the manufacture of chemicals with more complex structures, such as ethylbenzene and cumene, of which billions of kilograms are produced annually. Although benzene is a major Chemical industry, industrial che ...
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Reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a substance ''consumed'' in the course of a chemical reaction. ''Solvents'', though involved in the reaction mechanism, are usually not called reactants. Similarly, ''catalysts'' are not consumed by the reaction, so they are not reactants. In biochemistry, especially in connection with enzyme-catalyzed reactions, the reactants are commonly called substrates. Definitions Organic chemistry In organic chemistry, the term "reagent" denotes a chemical ingredient (a compound or mixture, typically of inorganic or small organic molecules) introduced to cause the desired transformation of an organic substance. Examples include the Collins reagent, Fenton's reagent, and Grignard reagents. Analytical chemistry In analytical chemistry, a reag ...
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Barium
Barium is a chemical element; it has symbol Ba and atomic number 56. It is the fifth element in group 2 and is a soft, silvery alkaline earth metal. Because of its high chemical reactivity, barium is never found in nature as a free element. The most common minerals of barium are barite ( barium sulfate, BaSO4) and witherite ( barium carbonate, BaCO3). The name ''barium'' originates from the alchemical derivative "baryta", from Greek (), meaning 'heavy'. ''Baric'' is the adjectival form of barium. Barium was identified as a new element in 1772, but not reduced to a metal until 1808 with the advent of electrolysis. Barium has few industrial applications. Historically, it was used as a getter for vacuum tubes and in oxide form as the emissive coating on indirectly heated cathodes. It is a component of YBCO (high-temperature superconductors) and electroceramics, and is added to steel and cast iron to reduce the size of carbon grains within the microstructure. Barium compounds ...
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Trifluoromethanesulfonic Acid
Triflic acid, the short name for trifluoromethanesulfonic acid, TFMS, TFSA, HOTf or TfOH, is a sulfonic acid with the chemical formula CF3SO3H. It is one of the strongest known acids. Triflic acid is mainly used in research as a catalyst for esterification. It is a hygroscopic, colorless, slightly viscous liquid and is soluble in polar solvents. Synthesis Trifluoromethanesulfonic acid is produced industrially by electrochemical fluorination (ECF) of methanesulfonic acid CH3SO3H + 4 HF ->CF3SO2F + H2O + 3 H2 The resulting CF3SO2F is hydrolyzed, and the resulting triflate salt is reprotonated. Alternatively, trifluoromethanesulfonic acid arises by oxidation of trifluoromethylsulfenyl chloride: CF3SCl + 2 Cl2 + 3 H2O -> CF3SO3H + 5 HCl Triflic acid is purified by distillation from triflic anhydride. Historical Trifluoromethanesulfonic acid was first synthesized in 1954 by Robert Haszeldine and Kidd by the following reaction: : Reactions As an acid In the laboratory, tr ...
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Dilute Sulfuric Acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen, and hydrogen, with the molecular formula . It is a colorless, odorless, and viscous liquid that is miscible with water. Pure sulfuric acid does not occur naturally due to its strong affinity to water vapor; it is hygroscopic and readily absorbs water vapor from the air. Concentrated sulfuric acid is a strong oxidant with powerful dehydrating properties, making it highly corrosive towards other materials, from rocks to metals. Phosphorus pentoxide is a notable exception in that it is not dehydrated by sulfuric acid but, to the contrary, dehydrates sulfuric acid to sulfur trioxide. Upon addition of sulfuric acid to water, a considerable amount of heat is released; thus, the reverse procedure of adding water to the acid is generally avoided since the heat released may boil the ...
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Silver Carbonate
Silver carbonate is the chemical compound with the formula Ag2 C O3. This salt 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. Preparation and reactions Silver carbonate can be prepared by combining aqueous solutions of sodium carbonate with a deficiency of silver nitrate. : Freshly prepared silver carbonate is colourless, but the solid quickly turns yellow. Silver carbonate reacts with ammonia to give the diamminesilver(I) ( g(NH3)2sup>+) complex ion. Like other diamminesilver(I) solutions, including Tollen's reagent, there is a possibility that explosive Silver nitride may precipitate out of the solution. Silver nitride was previously known as fulminating silver but due to confusions with silver fulminate it has been discontinued by the IUPAC. With hydrofluoric acid, it gives silver fluoride. The thermal conversion of silver carbonate to silver metal proceeds via for ...
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Recrystallization (chemistry)
Recrystallization is a broad class of List of purification methods in chemistry , chemical purification techniques characterized by the dissolution of an impure sample in a solvent or solvent mixture, followed by some change in conditions that encourages the formation of pure isolate as solid crystals. Recrystallization as a purification technique is driven by spontaneous process , spontaneous processes of molecular self-assembly , self-assembly that leverage the highly ordered (i.e. low-entropy) and periodic characteristics of a crystal's molecular structure to produce purification. Basic principles The driving force of this purification emerges from the difference in molecular interactions between the isolate and the impurities: if a molecule of the desired isolate interacts with any isolate crystal present, it is likely the molecule Deposition (chemistry) , deposits on the crystal's ordered surface and contributes to the crystal's growth; if a molecule of the impurity inter ...
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Tetrachloromethane
Carbon tetrachloride, also known by many other names (such as carbon tet for short and tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC), is a chemical compound with the chemical formula CCl4. It is a non-flammable, dense, colourless liquid with a "sweet" chloroform-like odour that can be detected at low levels. It was formerly widely used in fire extinguishers, as a precursor to refrigerants, an anthelmintic and a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride can affect the central nervous system and degenerate the liver and kidneys. Prolonged exposure can be fatal. Properties In the carbon tetrachloride molecule, four chlorine atoms are positioned symmetrically as corners in a tetrahedron, tetrahedral configuration joined to a central carbon atom by single covalent bonds. Because of this symmetric geometry, CCl4 is non-polar. methane, ...
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Diethyl Ether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs to the ether class of organic compounds. It is a common solvent and was formerly used as a general anesthetic. Production Most diethyl ether is produced as a byproduct of the vapor-phase Hydration reaction, hydration of ethylene to make ethanol. This process uses solid-supported phosphoric acid Catalysis, catalysts and can be adjusted to make more ether if the need arises: Vapor-phase Dehydration reaction, dehydration of ethanol over some Aluminium oxide, alumina catalysts can give diethyl ether yields of up to 95%. : Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Uses The dominant use of diethyl ether is as a solvent. One particular application is in the production of cell ...
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Silver Oxide
Silver oxide is the chemical compound with the formula Ag2 O. 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 an alkali hydroxide. This reaction does not afford appreciable amounts of silver hydroxide due to the favorable energetics for the following reaction: :( p''K'' = 2.875) With suitably controlled conditions, this reaction can be used to prepare Ag2O powder with properties suitable for several uses including as a fine grained conductive paste filler. Structure and properties Ag2O features linear, two-coordinate Ag centers linked by tetrahedral oxides. It is isostructural with Cu2O. It "dissolves" in solvents that degrade it. It is slightly soluble in water due to the formation of the ion and possibly related hydrolysis products. It is soluble in ammonia solution, producing active compound of Tollens' reagent. A slurry of Ag2O is readil ...
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