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Allene
In organic chemistry, allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon centres (). Allenes are classified as diene#Classes, cumulated dienes. The parent compound of this class is propadiene, which is itself also called ''allene''. Compounds with an allene-type structure but with more than three carbon atoms are members of a larger class of compounds called cumulenes with bonding. History For many years, allenes were viewed as curiosities but thought to be synthetically useless and difficult to prepare and to work with.The Chemistry of the Allenes (vol. 1−3); Landor, S. R., Ed.; cademic Press: London, 1982. Reportedly, the first synthesis of an allene, glutinic acid, was performed in an attempt to prove the non-existence of this class of compounds. The situation began to change in the 1950s, and more than 300 papers on allenes have been published in 2012 alone. These compounds are not just interesting intermediates ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Allene
In organic chemistry, allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon centres (). Allenes are classified as diene#Classes, cumulated dienes. The parent compound of this class is propadiene, which is itself also called ''allene''. Compounds with an allene-type structure but with more than three carbon atoms are members of a larger class of compounds called cumulenes with bonding. History For many years, allenes were viewed as curiosities but thought to be synthetically useless and difficult to prepare and to work with.The Chemistry of the Allenes (vol. 1−3); Landor, S. R., Ed.; cademic Press: London, 1982. Reportedly, the first synthesis of an allene, glutinic acid, was performed in an attempt to prove the non-existence of this class of compounds. The situation began to change in the 1950s, and more than 300 papers on allenes have been published in 2012 alone. These compounds are not just interesting intermediates ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Allene Symmetry
In organic chemistry, allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon centres (). Allenes are classified as cumulated dienes. The parent compound of this class is propadiene, which is itself also called ''allene''. Compounds with an allene-type structure but with more than three carbon atoms are members of a larger class of compounds called cumulenes with bonding. History For many years, allenes were viewed as curiosities but thought to be synthetically useless and difficult to prepare and to work with.The Chemistry of the Allenes (vol. 1−3); Landor, S. R., Ed.; cademic Press: London, 1982. Reportedly, the first synthesis of an allene, glutinic acid, was performed in an attempt to prove the non-existence of this class of compounds. The situation began to change in the 1950s, and more than 300 papers on allenes have been published in 2012 alone. These compounds are not just interesting intermediates but synthetica ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Propadiene
Propadiene () or allene () is the organic compound with the formula . It is the simplest allene, i.e. a compound with two adjacent carbon double bonds. As a constituent of MAPP gas, it has been used as a fuel for specialized welding. Production and equilibrium with methylacetylene Allene exists in equilibrium with methylacetylene (propyne) and the mixture is sometimes called MAPD for ''m''ethyl''a''cetylene-''p''ropa''d''iene: :H3CC#CH <<=> H2C=C=CH2 for which at 270 °C or 0.1 at 5 °C. MAPD is produced as a side product, often an undesirable one, of of to produce , an important |
Doering–LaFlamme Allene Synthesis
In organic chemistry, the Doering–LaFlamme allene synthesis is a reaction of alkenes that converts them to allenes by insertion of a carbon atom. This name reaction is named for William von Eggers Doering and a co-worker, who first reported it. The reaction is a two-stage process, in which first the alkene is reacted with dichlorocarbene or dibromocarbene to form a dihalocyclopropane. This intermediate is then reacted with a reducing metal, such as sodium or magnesium, or with an organolithium reagent. Either approach results in metal-halogen exchange to convert the ''gem''-dihalogenated carbon to a 1-metallo-1-halocyclopropane. This species undergoes α-elimination of metal halide and ring-opening via an electrocyclic reaction (at least formally) to give the allene. Several different reaction mechanism, mechanisms for the electrocyclic rearrangement have been studied. In a study in which an enantioenriched substituted cyclopropyl Grignard reagent was prepared, the reaction wa ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Glutinic Acid
Penta-2,3-dienedioic acid (one of two chemicals called glutinic acid), is in allene-containing dicarboxylic acid. It was the first allene to be synthesized, in 1887, but the structure of it was thought to be a propyne core instead of an allene. The correct structural isomeric identity was not determined until 1954. Literature confusion A diterpene, chemical name (4a''R'',5''S'',6''R'',8a''R'')-5- ''Z'')-4-carboxy-3-methylbut-3-enyl5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid (), is also called ''glutinic acid''. Some database entries for "glutinic acid" incorrectly identify it as this diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ... rather than the allene meaning in the underlying publications.See patents listed for References {{organic-c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Penta-2,3-dienedioic Acid
Penta-2,3-dienedioic acid (one of two chemicals called glutinic acid), is in allene-containing dicarboxylic acid. It was the first allene to be synthesized, in 1887, but the structure of it was thought to be a propyne core instead of an allene. The correct structural isomeric identity was not determined until 1954. Literature confusion A diterpene, chemical name (4a''R'',5''S'',6''R'',8a''R'')-5- ''Z'')-4-carboxy-3-methylbut-3-enyl5,6,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylic acid (), is also called ''glutinic acid''. Some database entries for "glutinic acid" incorrectly identify it as this diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ... rather than the allene meaning in the underlying publications.See patents listed for References {{organic-c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Skattebøl Rearrangement
The Skattebøl rearrangement is an organic reaction for converting a geminal dihalo cyclopropane to an allene using an organolithium base. This rearrangement reaction is named after its discoverer, Lars Skattebøl, Professor emeritus at the University of Oslo. It proceeds through a carbene reaction intermediate: When the cyclopropane ring is fitted with a 2-vinyl group, a cyclopentadiene is formed through a so-called foiled carbene intermediate.Leo A. Paquette and Mark L. McLaughlin Organic Syntheses, CV 8, 22Link This process is more generally known as a vinylcyclopropane rearrangement The vinylcyclopropane rearrangement or vinylcyclopropane-cyclopentene rearrangement is a ring expansion reaction, converting a vinyl-substituted cyclopropane ring into a cyclopentene ring. Intense experimental as well as computational investigati .... The reaction is closely related to the earlier Doering-LaFlamme procedure ( Doering-LaFlamme allene synthesis), in which a ''gem-''dibromocyclo ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
MAPP Gas
MAPP gas was a trademarked name, belonging to The Linde Group, a division of the former global chemical giant Union Carbide, for a fuel gas based on a stabilized mixture of methylacetylene (propyne), propadiene and propane. The name comes from the original chemical composition, methylacetylene-propadiene propane. "MAPP gas" is also widely used as a generic name for UN 1060 stabilised methylacetylene-propadiene (unstabilised methylacetylene-propadiene is known as MAPD). MAPP gas is widely regarded as a safer and easier-to-use substitute for acetylene. In early 2008, true MAPP gas production ended in North America when production was discontinued at the only remaining plant in North America that still manufactured it. However, many current products labeled "MAPP" are, in fact, MAPP ''substitutes.'' These versions contain mostly propylene with some propane, dimethyl ether is included as a 3rd ingredient in some versions. Use Genuine MAPP gas can be used in combination with oxygen ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bond Dipole Moment
In chemistry, polarity is a separation of electric charge leading to a molecule or its chemical groups having an electric dipole moment, with a negatively charged end and a positively charged end. Polar molecules must contain one or more polar bonds due to a difference in electronegativity between the bonded atoms. Molecules containing polar bonds have no molecular polarity if the bond dipoles cancel each other out by symmetry. Polar molecules interact through dipole–dipole intermolecular forces and hydrogen bonds. Polarity underlies a number of physical properties including surface tension, solubility, and melting and boiling points. Polarity of bonds Not all atoms attract electrons with the same force. The amount of "pull" an atom exerts on its electrons is called its electronegativity. Atoms with high electronegativitiessuch as fluorine, oxygen, and nitrogenexert a greater pull on electrons than atoms with lower electronegativities such as alkali metals and alkaline ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylacetylene
Propyne (methylacetylene) is an alkyne with the chemical formula . It is a component of MAPD gas—along with its isomer propadiene (allene), which was commonly used in gas welding. Unlike acetylene, propyne can be safely condensed.Peter Pässler, Werner Hefner, Klaus Buckl, Helmut Meinass, Andreas Meiswinkel, Hans-Jürgen Wernicke, Günter Ebersberg, Richard Müller, Jürgen Bässler, Hartmut Behringer, Dieter Mayer, "Acetylene" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim 2007 (). Production and equilibrium with propadiene Propyne exists in equilibrium with propadiene, the mixture of propyne and propadiene being called MAPD: :H3CC#CH H2C=C=CH2 The coefficient of equilibrium ''K''eq is 0.22 at 270 °C or 0.1 at 5 °C. MAPD is produced as a side product, often an undesirable one, by cracking propane to produce propene, an important feedstock in the chemical industry. MAPD interferes with the catalytic polymerization of propene. Laborato ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Proton Affinity
The proton affinity (PA, ''E''pa) of an anion or of a neutral atom or molecule is the negative of the enthalpy change in the reaction between the chemical species concerned and a proton in the gas phase: ::: A- + H+ -> HA ::: B + H+ -> BH+ These reactions are always exothermic in the gas phase, i.e. energy is released (enthalpy is negative) when the reaction advances in the direction shown above, while the proton affinity is positive. This is the same sign convention used for electron affinity. The property related to the proton affinity is the gas-phase basicity, which is the negative of the Gibbs energy for above reactions, i.e. the gas-phase basicity includes entropic terms in contrast to the proton affinity. Acid/base chemistry The higher the proton affinity, the stronger the base and the weaker the conjugate acid ''in the gas phase''. The (reportedly) strongest known base is the ortho-diethynylbenzene dianion (''E''pa = 1843 kJ/mol), followed by the methanide ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
