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Organolead Compound
Organolead compounds are chemical compounds containing a chemical bond between carbon and lead. Organolead chemistry is the corresponding science. The first organolead compound was hexaethyldilead (Pb2(C2H5)6), first synthesized in 1858.''Main Group Metals in Organic Synthesis'' Yamamoto, Hisashi / Oshima, Koichiro (eds.) 2004 Sharing the same group with carbon, lead is tetravalent. Going down the carbon group the C–''X'' (''X'' = C, Si, Ge, Sn, Pb) bond becomes weaker and the bond length larger. The C–Pb bond in tetramethyllead is 222 pm long with a dissociation energy of 49 kcal/ mol (204 kJ/mol). For comparison the C–Sn bond in tetramethyltin is 214 pm long with dissociation energy 71 kcal/mol (297 kJ/mol). The dominance of Pb(IV) in organolead chemistry is remarkable because inorganic lead compounds tend to have Pb(II) centers. The reason is that with inorganic lead compounds elements such as nitrogen, oxygen and the halides have a much higher electronegativity than le ...
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Electronegativity
Electronegativity, symbolized as , is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. An atom's electronegativity is affected by both its atomic number and the distance at which its valence electrons reside from the charged nucleus. The higher the associated electronegativity, the more an atom or a substituent group attracts electrons. Electronegativity serves as a simple way to quantitatively estimate the bond energy, and the sign and magnitude of a bond's chemical polarity, which characterizes a bond along the continuous scale from covalent to ionic bonding. The loosely defined term electropositivity is the opposite of electronegativity: it characterizes an element's tendency to donate valence electrons. On the most basic level, electronegativity is determined by factors like the nuclear charge (the more protons an atom has, the more "pull" it will have on electrons) and the number and location ...
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Sodium Cyclopentadienide
Sodium cyclopentadienide is an organosodium compound with the formula C5H5Na. The compound is often abbreviated as NaCp, where Cp− is the cyclopentadienide anion. Sodium cyclopentadienide is a colorless solid, although samples often are pink owing to traces of oxidized impurities. Preparation Sodium cyclopentadienide is commercially available as a solution in THF. It is prepared by treating cyclopentadiene with sodium: : The conversion can be conducted by heating a suspension of molten sodium in dicyclopentadiene.Tarun K. Panda, Michael T. Gamer, Peter W. Roesky "An Improved Synthesis of Sodium and Potassium Cyclopentadienide" Organometallics, 2003, 22, 877–878. In former times, the sodium was provided in the form of "sodium wire" or "sodium sand", a fine dispersion of sodium prepared by melting sodium in refluxing xylene and rapidly stirring. Sodium hydride is a convenient base: : In early work, Grignard reagents were used as bases. With a p''K''a of 15, cyclopen ...
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Boiling Point
The boiling point of a substance is the temperature at which the vapor pressure of a liquid equals the pressure surrounding the liquid and the liquid changes into a vapor. The boiling point of a liquid varies depending upon the surrounding environmental pressure. A liquid in a partial vacuum has a lower boiling point than when that liquid is at atmospheric pressure. A liquid at low pressure has a lower boiling point than when that liquid is at atmospheric pressure. Because of this, water boils at under standard pressure at sea level, but at at altitude. For a given pressure, different liquids will boiling, boil at different temperatures. The normal boiling point (also called the atmospheric boiling point or the atmospheric pressure boiling point) of a liquid is the special case in which the vapor pressure of the liquid equals the defined atmospheric pressure at sea level, one Atmosphere (unit), atmosphere. At that temperature, the vapor pressure of the liquid becomes suffici ...
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Methylmagnesium Chloride
Methylmagnesium chloride is an organometallic compound with the general formula CH3MgCl. This highly flammable, colorless, and moisture sensitive material is the simplest Grignard reagent and is commercially available, usually as a solution in tetrahydrofuran. Synthesis and reactions Relative to the more commonly encountered methylmagnesium bromide and methylmagnesium iodide, methylmagnesium chloride offers the advantages of low equivalent weight and low cost. It is prepared by the reaction of methyl chloride and magnesium in ethyl ether. left, Structure of CH3MgCl(thf)2, which is representative of the species in donor solvents. As with most Grignard reagents, methylmagnesium chloride is highly solvated by ether solvents via coordination from two oxygen atoms to give a tetrahedrally bonded magnesium center. Like methyllithium, it is the synthetic equivalent to the methyl carbanion synthon. It reacts with water and other protic reagents to give methane, e.g.,: :CH3MgCl + ...
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Lead Chloride
Lead chloride may refer to: * Lead(II) chloride (plumbous chloride), mineral name: cotunnite Cotunnite is the natural mineral form of lead(II) chloride with formula PbCl2. It was first described in 1825 from an occurrence on Mount Vesuvius, Naples Province, Campania, Italy. It was named for Domenico Cotugno (Cotunnius) (1736–1822), Ita .... * Lead(IV) chloride (plumbic chloride) {{Short pages monitor ...
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Grignard Reagent
A Grignard reagent or Grignard compound is a chemical compound with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromide . They are a subclass of the organomagnesium compounds. Grignard compounds are popular reagents in organic synthesis for creating new carbon-carbon bonds. For example, when reacted with another halogenated compound in the presence of a suitable catalyst, they typically yield and the magnesium halide as a byproduct; and the latter is insoluble in the solvents normally used. In this aspect, they are similar to organolithium reagents. Pure Grignard reagents are extremely reactive solids. They are normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran; which are relatively stable as long as water is excluded. In such a medium, a Grignard reagent is invariably present as a complex with the magnesium atom conn ...
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Lead(II) Chloride
Lead(II) chloride (PbCl2) is an inorganic compound which is a white solid under ambient conditions. It is poorly soluble in water. Lead(II) chloride is one of the most important lead-based reagents. It also occurs naturally in the form of the mineral cotunnite. Structure and properties In solid PbCl2, each lead ion is coordinated by nine chloride ions in a tricapped triangular prism formation — six lie at the vertices of a triangular prism and three lie beyond the centers of each rectangular prism face. The 9 chloride ions are not equidistant from the central lead atom, 7 lie at 280–309 pm and 2 at 370 pm. PbCl2 forms white orthorhombic needles. File:Cotunnite-3D-balls.png, Ball-and-stick model of part of the crystal structure of cotunnite File:Cotunnite-3D-ionic.png, Space-filling model File:Cotunnite-Pb-coordination-geometry-3D-balls.png, Coordination geometry of Pb2+ File:Cotunnite-Cl-coordination-geometry-3D-balls.png, Coordination geometry of Cl− File:Cot ...
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Lead Tetraacetate
Lead(IV) acetate or lead tetraacetate is an organometallic compound with chemical formula . It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis. Structure In the solid state the lead(IV) centers are coordinated by four acetate ions, which are bidentate, each coordinating via two oxygen atoms. The lead atom is 8 coordinate and the O atoms form a flattened trigonal dodecahedron. Preparation It is typically prepared by treating of red lead with acetic acid and acetic anhydride (), which absorbs water. The net reaction is shown: :Pb3O4 + 4 Ac2O -> Pb(OAc)4 + 2 Pb(OAc)2 The remaining lead(II) acetate can be partially oxidized to the tetraacetate: :2 Pb(OAc)2 + Cl2 -> Pb(OAc)4 + PbCl2 Reagent in organic chemistry Lead tetraacetate is a strong oxidizing agent, a source of acetyloxy groups and a general rea ...
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Internal Combustion Engines
An internal combustion engine (ICE or IC engine) is a heat engine in which the combustion of a fuel occurs with an oxidizer (usually air) in a combustion chamber that is an integral part of the working fluid flow circuit. In an internal combustion engine, the expansion of the high-temperature and high-pressure gases produced by combustion applies direct force to some component of the engine. The force is typically applied to pistons ( piston engine), turbine blades (gas turbine), a rotor (Wankel engine), or a nozzle ( jet engine). This force moves the component over a distance, transforming chemical energy into kinetic energy which is used to propel, move or power whatever the engine is attached to. This replaced the external combustion engine for applications where the weight or size of an engine was more important. The first commercially successful internal combustion engine was created by Étienne Lenoir around 1860, and the first modern internal combustion engine, know ...
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Gasoline
Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic compounds obtained by the fractional distillation of petroleum, enhanced with a variety of additives. On average, U.S. refineries produce, from a barrel of crude oil, about 19 to 20 gallons of gasoline; 11 to 13 gallons of distillate fuel (most of which is sold as diesel fuel); and 3 to 4 gallons of jet fuel. The product ratio depends on the processing in an oil refinery and the crude oil assay. A barrel of oil is defined as holding 42 US gallons, which is about 159 liters or 35 imperial gallons. The characteristic of a particular gasoline blend to resist igniting too early (which causes knocking and reduces efficiency in reciprocating engines) is measured by its octane rating, which is produced in several grades. Tetraethyl lead and o ...
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Antiknock Agent
An antiknock agent is a gasoline additive used to reduce engine knocking and increase the fuel's octane rating by raising the temperature and pressure at which auto-ignition occurs. The mixture known as gasoline or petrol, when used in high compression internal combustion engines, has a tendency to knock (also called "pinging" or "pinking") and/or to ignite early before the correctly timed spark occurs (''pre-ignition'', refer to engine knocking). Notable early antiknock agents, especially Tetraethyllead, added to gasoline included large amounts of toxic lead. The chemical was responsible for global negative impacts on health, and the phase out of leaded gasoline from the 1970s onward was reported by the UN to be responsible for $2.4 trillion in annual benefits, 1.2 million fewer premature deaths, higher overall intelligence and 58 million fewer crimes," the United Nations Environmental Programme said. Some other chemicals used as gasoline additives are thought to be less toxic ...
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