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Triphenylmethyl Chloride
Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C19H15Cl. It is an alkyl halide, sometimes used to introduce the trityl protecting group. Preparation Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of triphenylmethanol with acetyl chloride, or by the Friedel–Crafts alkylation of benzene with carbon tetrachloride to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed. Reactions Triphenylmethylsodium can be prepared from trityl chloride dissolved in an aprotic solvent and sodium: :(C6H5)3CCl + 2 Na → (C6H5)3CNa + NaCl Reaction with silver hexafluorophosphate gives triphenylmethyl hexafluorophosphate. Trityl chloride reacts with zinc in nonpolar solvents (e.g. benzene) to form Gomberg's dimer.{{cite journal , last1=Gomberg , first1=M. , title=An Instance of Trivalent Carbon: Triphenylmethyl , journal=Journal of the American Chemical Society , date=1900 , volume ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
MmHg
A millimetre of mercury is a manometric unit of pressure, formerly defined as the extra pressure generated by a column of mercury one millimetre high, and currently defined as exactly pascals. It is denoted mmHg or mm Hg. Although not an SI unit, the millimetre of mercury is still routinely used in medicine, meteorology, aviation, and many other scientific fields. One millimetre of mercury is approximately 1 Torr, which is of standard atmospheric pressure ( ≈ ). Although the two units are not equal, the relative difference (less than ) is negligible for most practical uses. History For much of human history, the pressure of gases like air was ignored, denied, or taken for granted, but as early as the 6th century BC, Greek philosopher Anaximenes of Miletus claimed that all things are made of air that is simply changed by varying levels of pressure. He could observe water evaporating, changing to a gas, and felt that this applied even to solid matter. More cond ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triphenylmethylsodium
Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical). Preparation Triphenylmethane was first synthesized in 1872 by the German chemist August Kekulé and his Belgian student Antoine Paul Nicolas Franchimont (1844–1919) by heating diphenylmercury (Hg(C6H5)2, ''Quecksilberdiphenyl'') with benzal chloride (C6H5CHCl2, ''Benzylenchlorid''). Triphenylmethane can be synthesized by Friedel–Crafts reaction from benzene and chloroform with aluminium chloride catalyst: :3 C6H6 + CHCl3 → Ph3CH + 3 HCl Alternatively, benzene may react with carbon tetrachloride usi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkylating Agents
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion (carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent bond be ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triphenylmethanol
Triphenylmethanol (also known as triphenylcarbinol, TrOH) is an organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol, diethyl ether, and benzene. In strongly acidic solutions, it produces an intensely yellow color, due to the formation of a stable "trityl" carbocation. Many derivatives of triphenylmethanol are important dyes. History After the German chemist August Kekulé and his Belgian student Antoine Paul Nicolas Franchimont (1844–1919) first synthesized triphenylmethane in 1872, the Russian doctoral student Walerius Hemilian (1851–1914) first synthesized triphenylmethanol in 1874 by reacting triphenylmethyl bromide with water as well as by oxidizing triphenylmethane. Structure and properties Triphenylmethanol features three phenyl (Ph) rings and an alcohol group bound to a central tetrahedral carbon atom. All three C–Ph bonds are typical of ''sp''3-''sp''2 carbon-carbon bonds with lengths of appr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triphenylmethyl Hexafluorophosphate
Triphenylmethyl (also triphenylcarbenium, trityl, or tritylium) hexafluorophosphate is an organic salt with the formula or , consisting of the triphenylmethyl cation and the hexafluorophosphate anion . Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses. Preparation Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride: :AgPF6 + (C6H5)3CCl → (C6H5)3CPF6 + AgCl A second method involves protonolysis of trityl hydroxide: :HPF6 + (C6H5)3COH → (C6H5)3CPF6 + H2O Structure and reactions Triphenylmethyl hexafluorophosphate readily hydrolyzes, in a reaction that is the reverse of one of its syntheses: :(C6H5)3CPF6 + H2O → (C6H5)3COH + HPF6 Triphenylmethyl hexafluorophosphate has been used for abstracting hydride () from organic compounds. Treatment of metal-alkene and diene complexes one can generate ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triphenylmethane
Triphenylmethane, or triphenyl methane, is the hydrocarbon with the formula (C6H5)3CH. This colorless solid is soluble in nonpolar organic solvents and not in water. Triphenylmethane is the basic skeleton of many synthetic dyes called triarylmethane dyes, many of them are pH indicators, and some display fluorescence. A trityl group in organic chemistry is a triphenylmethyl group Ph3C, e.g. triphenylmethyl chloride (trityl chloride) and the triphenylmethyl radical (trityl radical). Preparation Triphenylmethane was first synthesized in 1872 by the German chemist August Kekulé and his Belgian student Antoine Paul Nicolas Franchimont (1844–1919) by heating diphenylmercury (Hg(C6H5)2, ''Quecksilberdiphenyl'') with benzal chloride (C6H5CHCl2, ''Benzylenchlorid''). Triphenylmethane can be synthesized by Friedel–Crafts reaction from benzene and chloroform with aluminium chloride catalyst: :3 C6H6 + CHCl3 → Ph3CH + 3 HCl Alternatively, benzene may react with carbon tetrachloride us ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triphenylmethyl Radical
The triphenylmethyl radical (often shorted to trityl radical) is an organic compound with the formula (C6H5)3C. It is a persistent radical. It was the first radical ever to be described in organic chemistry. Because of its accessibility, the trityl radical has been heavily exploited. Preparation and properties It can be prepared by homolysis of triphenylmethyl chloride 1 by a metal like silver or zinc in benzene or diethyl ether. The radical 2 forms a chemical equilibrium with the quinoid-type dimer 3 (Gomberg's dimer). In benzene the concentration of the radical is 2%. Solutions containing the radical are yellow; when the temperature of the solution is raised, the yellow color becomes more intense as the equilibrium is shifted in favor of the radical (in accordance with Le Chatelier's principle). When exposed to air, the radical rapidly oxidizes to the peroxide, and the color of the solution changes from yellow to colorless. Likewise, the radical reacts with iodine to tri ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Gomberg's Dimer
Gomberg's dimer is the organic compound with the formula Ph2C=C6H5-CPh3, where Ph = C6H5. It is a yellow solid that is air-stable for hours at room temperature and soluble in organic solvents. The compound achieved fame as the dimer of triphenylmethyl radical, which was prepared by Moses Gomberg in his quest for hexaphenylethane. Its quinoid structure has been determined by X-ray crystallography. The C-C bond that reversibly breaks is rather long at 159.7 picometers. Synthesis and reactions Gomberg's dimer can be prepared quantitatively by treating trityl bromide with powdered copper or silver: :2Ph3CBr + 2Cu → Ph2C=C6H5-CPh3 + 2CuBr Gomberg's dimer reversibly dissociates to the triphenylmethyl radical in organic solvents: : See also * Hexaphenylethane Hexaphenylethane is a hypothetical organic compound consisting of an ethane core with six phenyl substituents. All attempts at its synthesis have been unsuccessful. The trityl free radical, Ph3C, was originall ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triphenylmethyl Hexafluorophosphate
Triphenylmethyl (also triphenylcarbenium, trityl, or tritylium) hexafluorophosphate is an organic salt with the formula or , consisting of the triphenylmethyl cation and the hexafluorophosphate anion . Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to triphenylmethanol. It is used as a catalyst and reagent in organic syntheses. Preparation Triphenylmethyl hexafluorophosphate can be prepared by combining silver hexafluorophosphate with triphenylmethyl chloride: :AgPF6 + (C6H5)3CCl → (C6H5)3CPF6 + AgCl A second method involves protonolysis of trityl hydroxide: :HPF6 + (C6H5)3COH → (C6H5)3CPF6 + H2O Structure and reactions Triphenylmethyl hexafluorophosphate readily hydrolyzes, in a reaction that is the reverse of one of its syntheses: :(C6H5)3CPF6 + H2O → (C6H5)3COH + HPF6 Triphenylmethyl hexafluorophosphate has been used for abstracting hydride () from organic compounds. Treatment of metal-alkene and diene complexes one can generate ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Silver Hexafluorophosphate
Silver hexafluorophosphate, sometimes referred to "silver PF-6," is an inorganic compound with the chemical formula AgPF6. Uses and reactions Silver hexafluorophosphate is a commonly encountered reagent in inorganic and organometallic chemistry. It is commonly used to replace halide ligands with the weakly coordinating hexafluorophosphate anion; the abstraction of the halide is driven by the precipitation of the appropriate silver halide. Illustrative is the preparation of acetonitrile complexes from a metal bromide, a reaction that would typically be conducted in a solution of acetonitrile: :AgPF6 + Re(CO)5Br + CH3CN → AgBr + e(CO)5(CH3CN)F6 AgPF6 can act as an oxidant, forming silver metal as a by-product. For example, in solution in dichloromethane, ferrocene is oxidised to ferrocenium hexafluorophosphate: :AgPF6 + Fe(C5H5)2 → Ag + e(C5H5)2F6 (''E'' = 0.65 V) Related reagents In terms of their properties and applications, silver tetrafluoroborate (AgBF4) and the h ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sodium
Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable isotope is 23Na. The free metal does not occur in nature, and must be prepared from compounds. Sodium is the sixth most abundant element in the Earth's crust and exists in numerous minerals such as feldspars, sodalite, and halite (NaCl). Many salts of sodium are highly water-soluble: sodium ions have been leached by the action of water from the Earth's minerals over eons, and thus sodium and chlorine are the most common dissolved elements by weight in the oceans. Sodium was first isolated by Humphry Davy in 1807 by the electrolysis of sodium hydroxide. Among many other useful sodium compounds, sodium hydroxide (lye) is used in soap manufacture, and sodium chloride (edible salt) is a de-icing agent and a nutrient for animals including h ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbon Tetrachloride
Carbon tetrachloride, also known by many other names (such as tetrachloromethane, also IUPAC nomenclature of inorganic chemistry, recognised by the IUPAC, carbon tet in the cleaning industry, Halon-104 in firefighting, and Refrigerant-10 in HVACR) is an organic compound with the chemical formula CCl4. It is a colourless liquid with a "sweet" smell that can be detected at low levels. It is practically incombustible at lower temperatures. It was formerly widely used in fire extinguishers, as a precursor to refrigerants and as a cleaning agent, but has since been phased out because of environmental and safety concerns. Exposure to high concentrations of carbon tetrachloride (including vapor) 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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
