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Radical Ion
In organic chemistry, a radical anion is a free radical species that carries a negative charge. Radical anions are encountered in organic chemistry as reduced derivatives of polycyclic aromatic compounds, e.g. sodium naphthenide. An example of a non-carbon radical anion is the superoxide anion, formed by transfer of one electron to an oxygen molecule. Radical anions are typically indicated by M^. Polycyclic radical anions Many aromatic compounds can undergo one-electron reduction by alkali metals. The electron is transferred from the alkali metal ion to an unoccupied antibonding p-p п* orbital of the aromatic molecule. This transfer is usually only energetically favorable if the aprotic solvent efficiently solvates the alkali metal ion. Effective solvents are those that bind to the alkali metal cation: diethyl ether < < |
Sodium Naphthalenide
Sodium naphthalene is an organic salt with the chemical formula Na+. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It is usually generated in situ. When isolated, it invariably crystallizes as a solvate with ligands bound to Na+. Preparation and properties The alkali metal naphthalene salts are prepared by stirring the metal with naphthalene in an ethereal solvent, usually as tetrahydrofuran or dimethoxyethane. The resulting salt is dark green. The anion is a radical, giving a strong EPR signal near ''g'' = 2.0. Its deep green color arises from absorptions centered at 463 and 735 nm. Several solvates of sodium naphthalenide have been characterized by X-ray crystallography. The effects are subtle, the outer pair of CH−CH bonds contract by 3 pm and the other nine C−C bonds elongate by 2–3 pm. The net effect is that reduction weakens the bonding. Reactions ;Redox Wi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Anthracene
Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the Economic production, production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation. Occurrence and production Coal tar, which contains around 1.5% anthracene, remains a major source of this material. Common impurities are phenanthrene and carbazole. The mineral form of anthracene is called freitalite and is related to a coal deposit. A classic laboratory method for the preparation of anthracene is by cyclodehydration of o-methyl- or o-methylene-substituted diarylketones in the so-called Elbs reaction, for example from ''o''-tolyl phenyl ketone. Reactions Reduction Reduction of anthracene with alkali metals yields the deeply colored radical anion salts M+[anthracene]− (M = Li, Na, K). Hydrogenation gives 9 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Potassium
Potassium is the chemical element with the symbol K (from Neo-Latin ''kalium'') and atomic number19. Potassium is a silvery-white metal that is soft enough to be cut with a knife with little force. Potassium metal reacts rapidly with atmospheric oxygen to form flaky white potassium peroxide in only seconds of exposure. It was first isolated from potash, the ashes of plants, from which its name derives. In the periodic table, potassium is one of the alkali metals, all of which have a single valence electron in the outer electron shell, that is easily removed to create an ion with a positive charge – a cation, that combines with anions to form salts. Potassium in nature occurs only in ionic salts. Elemental potassium reacts vigorously with water, generating sufficient heat to ignite hydrogen emitted in the reaction, and burning with a lilac- colored flame. It is found dissolved in sea water (which is 0.04% potassium by weight), and occurs in many minerals such as orthoclase, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclooctatetraene
1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as nnulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of its stoichiometric relationship to benzene, COT has been the subject of much research and some controversy. Unlike benzene, C6H6, cyclooctatetraene, C8H8, is not aromatic, although its dianion, (cyclooctatetraenide), is. Its reactivity is characteristic of an ordinary polyene, i.e. it undergoes addition reactions. Benzene, by contrast, characteristically undergoes substitution reactions, not additions. History 1,3,5,7-Cyclooctatetraene was initially synthesized by Richard Willstätter in Munich in 1905 using pseudopelletierine as the starting material and the Hofmann elimination as the key transformation: : Willstätter noted that the compound did not exhibit the expected aromaticity. Between 1939 and 1943, chemists throughout the US u ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Perylene
Perylene or perilene is a polycyclic aromatic hydrocarbon with the chemical formula C20H12, occurring as a brown solid. It or its derivatives may be carcinogenic, and it is considered to be a hazardous pollutant. In cell membrane cytochemistry, perylene is used as a fluorescent lipid probe. It is the parent compound of a class of rylene dyes. Reactions Like other polycyclic aromatic compounds, perylene is reduced by alkali metals to give a deeply colored radical anion and a dianion. The diglyme solvates of these salts have been characterized by X-ray crystallography. Emission Perylene displays blue fluorescence. It is used as a blue-emitting dopant material in OLEDs, either pure or substituted. Perylene can be also used as an organic photoconductor. It has an absorption maximum at 434 nm, and as with all polycyclic aromatic compounds, low water solubility (1.2 x 10−5 mmol/L). Perylene has a molar absorptivity of 38,500 M−1cm−1 at 435.7 nm. Image:Perylene ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acenaphthylene
Acenaphthylene, a polycyclic aromatic hydrocarbon is an ortho- and peri-fused tricyclic hydrocarbon. The molecule resembles naphthalene with positions 1 and 8 connected by a -CH=CH- unit. It is a yellow solid. Unlike many polycyclic aromatic hydrocarbons, it has no fluorescence. Occurrence Acenaphthylene occurs as about 2% of coal tar. It is produced industrially by gas phase dehydrogenation of acenaphthene. Reactions Hydrogenation gives the more saturated compound acenaphthene Acenaphthene is a polycyclic aromatic hydrocarbon (PAH) consisting of naphthalene with an ethylene bridge connecting positions 1 and 8. It is a colourless solid. Coal tar consists of about 0.3% of this compound. Production and reactions Acena .... Chemical reduction affords the radical anion sodium or potassium acenaphthalenide, which is used as a strong reductant (E = -2.26 V vs FC).N. G. Connelly and W. E. Geiger, "Chemical Redox Agents for Organometallic Chemistry", Chem. Rev. 1996, 96, 877-910 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Biphenyl
Biphenyl (also known as diphenyl, phenylbenzene, 1,1′-biphenyl, lemonene or BP) is an organic compound that forms colorless crystals. Particularly in older literature, compounds containing the functional group consisting of biphenyl less one hydrogen (the site at which it is attached) may use the prefixes xenyl or diphenylyl. It has a distinctively pleasant smell. Biphenyl is an aromatic hydrocarbon with a molecular formula (C6H5)2. It is notable as a starting material for the production of polychlorinated biphenyls (PCBs), which were once widely used as dielectric fluids and heat transfer agents. Biphenyl is also an intermediate for the production of a host of other organic compounds such as emulsifiers, optical brighteners, crop protection products, and plastics. Biphenyl is insoluble in water, but soluble in typical organic solvents. The biphenyl molecule consists of two connected phenyl rings. Properties and occurrence Biphenyl occurs naturally in coal tar, crude oil, a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
1-Methylnaphthalene
1-Methylnaphthalene is an organic compound with the formula CH3C10H7. It is a colorless liquid. It is isomeric with 2-methylnaphthalene. Reference fuel 1-Methylnaphthalene defines the lower (zero) reference point of cetane number, a measure of diesel fuel ignition quality, as it has a long ignition delay (poor ignition qualities). In contrast, cetane, with its short ignition delay, defines the upper reference point at 100. In testing, isocetane (2,2,4,4,6,8,8-heptamethylnonane or HMN) replaced 1-methylnaphthalene as the low cetane number reference fuel in 1962 for reasons of better oxidation stability and ease of use in the reference engine. The scale is unchanged, as isocetane's cetane number is measured at 15, referenced to 1-methylnaphthalene and cetane. Methylnaphthalene anion With alkali metals, 1-methylnaphthalene forms radical anion salts such as sodium 1-methylnaphthalene. Compared to its structural analog sodium naphthalene Sodium naphthalene is an organic salt with th ... [...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] |
Sodium Naphthalene
Sodium naphthalene is an organic salt with the chemical formula Na+. In the research laboratory, it is used as a reductant in the synthesis of organic, organometallic, and inorganic chemistry. It is usually generated in situ. When isolated, it invariably crystallizes as a solvate with ligands bound to Na+. Preparation and properties The alkali metal naphthalene salts are prepared by stirring the metal with naphthalene in an ethereal solvent, usually as tetrahydrofuran or dimethoxyethane. The resulting salt is dark green. The anion is a radical, giving a strong EPR signal near ''g'' = 2.0. Its deep green color arises from absorptions centered at 463 and 735 nm. Several solvates of sodium naphthalenide have been characterized by X-ray crystallography. The effects are subtle, the outer pair of CH−CH bonds contract by 3 pm and the other nine C−C bonds elongate by 2–3 pm. The net effect is that reduction weakens the bonding. Reactions ;Redox Wi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lithium
Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid element. Like all alkali metals, lithium is highly reactive and flammable, and must be stored in vacuum, inert atmosphere, or inert liquid such as purified kerosene or mineral oil. When cut, it exhibits a metallic luster, but moist air corrodes it quickly to a dull silvery gray, then black tarnish. It never occurs freely in nature, but only in (usually ionic) compounds, such as pegmatitic minerals, which were once the main source of lithium. Due to its solubility as an ion, it is present in ocean water and is commonly obtained from brines. Lithium metal is isolated electrolytically from a mixture of lithium chloride and potassium chloride. The nucleus of the lithium atom verges on instability, since the two stable lithium isotopes foun ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
