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Organoaluminium Compound
Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer triisobutylaluminium, and the titanium-aluminium compound called Tebbe's reagent. The behavior of organoaluminium compounds can be understood in terms of the polarity of the C−Al bond and the high Lewis acidity of the three-coordinated species. Industrially, these compounds are mainly used for the production of polyolefins. History The first organoaluminium compound (C2H5)3Al2I3 was discovered in 1859. Organoaluminium compounds were, however, little known until the 1950s when Karl Ziegler and colleagues discovered the direct synthesis of trialkylaluminium compounds and applied these compounds to catalytic olefin polymerization. This line of research ultimately resulted in the Nobel Prize to Ziegler. Structure and bonding Aluminium( ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Side Chain
In organic chemistry and biochemistry, a side chain is a substituent, chemical group that is attached to a core part of the molecule called the "main chain" or backbone chain, backbone. The side chain is a hydrocarbon branching element of a molecule that is attached to a larger hydrocarbon backbone. It is one factor in determining a molecule's properties and reactivity. A side chain is also known as a pendant chain, but a pendant group (side group) has a different definition. Conventions The placeholder R is often used as a generic placeholder for alkyl (saturated hydrocarbon) group side chains in structural formulae. To indicate other non-carbon groups in structure diagrams, X, Y, or Z are often used. History The ''R'' symbol was introduced by 19th-century French chemist Charles Frédéric Gerhardt, who advocated its adoption on the grounds that it would be widely recognizable and intelligible given its correspondence in multiple European languages to the initial letter of "r ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diisobutylaluminium Hydride
Diisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the chemical formula, formula (''i''-Bu2AlH)2, where ''i''-Bu represents isobutyl (-CH2CH(CH3)2). This organoaluminium chemistry, organoaluminium compound is a reagent in organic synthesis. Properties Like most organoaluminum compounds, the compound's structure is most probably more than that suggested by its empirical formula. A variety of techniques, not including X-ray crystallography, suggest that the compound exists as a dimer (chemistry), dimer and a trimer, consisting of tetrahedral aluminium centers sharing bridging hydride ligands. Hydrides are small and, for aluminium derivatives, are highly base (chemistry), basic, thus they bridge in preference to the alkyl groups. DIBAL can be prepared by heating triisobutylaluminium (itself a dimer) to induce Beta-Hydride elimination, β-hydride elimination: :(''i''-Bu3Al)2 → (''i''-Bu2AlH)2 + 2 isobutene, (CH3)2C=CH2 Although DIBAL can be purcha ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triethylaluminium
Triethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name the compound has the formula Al2( C2H5)6 (abbreviated as Al2Et6 or TEA). This colorless liquid is pyrophoric. It is an industrially important compound, closely related to trimethylaluminium. Structure and bonding The structure and bonding in Al2R6 and diborane are analogous (R = alkyl). Referring to Al2Me6, the Al-C(terminal) and Al-C(bridging) distances are 1.97 and 2.14 Å, respectively. The Al center is tetrahedral. The carbon atoms of the bridging ethyl groups are each surrounded by five neighbors: carbon, two hydrogen atoms and two aluminium atoms. The ethyl groups interchange readily intramolecularly. At higher temperatures, the dimer cracks into monomeric AlEt3. Synthesis and reactions Triethylaluminium can be formed via several routes. The discovery of an efficient route was a significant technological achievement. The multistep process uses aluminium, hydrogen gas, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ethylaluminium Sesquichloride
Ethylaluminium sesquichloride, also called EASC, is an industrially important organoaluminium compound used primarily as a precursor to triethylaluminium and as a catalyst component in Ziegler–Natta type systems for olefin and diene polymerizations. Other applications include use in alkylation reactions and as a catalyst component in linear oligomerization and cyclization of unsaturated hydrocarbons. EASC is a colourless liquid, spontaneously combustible in air and reacts violently when in contact with water and many other compounds.Aluminum alkyls. Albemarle Corporation 2010 Production Methyl, ethyl, and other alkyl or aralkyl halides that are not dehydrohalogenated readily can react with aluminium in an exothermic process to form organoaluminiu ...[...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Grignard Reagent
Grignard reagents or Grignard compounds are chemical compounds 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. Grignard reagents are rarely isolated as solids. Instead, they are normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran using air-free techniques. Grignard reagents are complex with the magnesium atom bonded to two ether ligands as well as the halide and organyl ligands. The discovery of the Grignard reaction in 1900 was recogn ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Alkylation
Alkylation is a chemical reaction that entails transfer of an alkyl group. 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 alkene, 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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Isobutyl
In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula , derived from either of the two isomers (''n''-butane and isobutane) of butane. The isomer ''n''-butane can connect in two ways, giving rise to two "-butyl" groups: * If it connects at one of the two terminal carbon atoms, it is normal butyl or ''n''-butyl: (preferred IUPAC name: butyl) * If it connects at one of the non-terminal (internal) carbon atoms, it is secondary butyl or ''sec''-butyl: (preferred IUPAC name: butan-2-yl) The second isomer of butane, isobutane, can also connect in two ways, giving rise to two additional groups: * If it connects at one of the three terminal carbons, it is isobutyl: (preferred IUPAC name: 2-methylpropyl) * If it connects at the central carbon, it is tertiary butyl, ''tert''-butyl or ''t''-butyl: (preferred IUPAC name: ''tert''-butyl) Nomenclature According to IUPAC nomenclature, "isobutyl", "''sec''-butyl", and "''tert''- ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pentamethylcyclopentadiene
1,2,3,4,5-Pentamethylcyclopentadiene is a cyclic compound, cyclic diene with the formula , often written , where Me is Methyl group, . It is a colorless liquid. 1,2,3,4,5-Pentamethylcyclopentadiene is the precursor to the ligand ''1,2,3,4,5-pentamethylcyclopentadienyl'', which is often denoted Cp* () and read as "C P star", the "star" signifying the five methyl groups radiating from the core of the ligand. Thus, the 1,2,3,4,5-pentamethylcyclopentadiene's formula is also written Cp*H. In contrast to less-substituted cyclopentadiene derivatives, Cp*H is not prone to dimerization. Synthesis Pentamethylcyclopentadiene is commercially available. It was first prepared from tiglaldehyde and 2-butenyllithium, via 2,3,4,5-tetramethylcyclopent-2-enone, with a Nazarov cyclization reaction as a key step. : Alternatively, 2-butenyllithium adds to ethyl acetate followed by acid-catalyzed dehydrocyclization: : : Organometallic derivatives Cp*H is a precursor to organometallic compounds con ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrahedrane
Tetrahedrane is a hypothetical platonic hydrocarbon with chemical formula and a tetrahedral structure. The molecule would be subject to considerable angle strain and has not been synthesized . However, a number of derivatives have been prepared. In a more general sense, the term ''tetrahedranes'' is used to describe a class of molecules and ions with related structure, e.g. white phosphorus. C4 tetrahedranes Tetrahedrane () is one of the possible platonic hydrocarbons and has the IUPAC name tricyclo .1.0.02,4utane. Unsubstituted tetrahedrane remains elusive, although predicted kinetically stable. One strategy that has been explored (but thus far failed) is reaction of propene with atomic carbon. Contrariwise, several organic compounds with the tetrahedrane core are known. All have multiply bulky substituents, ''tert''-butyl (''t''-Bu) or larger. Locking a tetrahedrane molecule inside a fullerene has only been attempted ''in silico''. All known syntheses have ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Octet Rule
The octet rule is a chemical rule of thumb that reflects the theory that main-group elements tend to bond in such a way that each atom has eight electrons in its valence shell, giving it the same electronic configuration as a noble gas. The rule is especially applicable to carbon, nitrogen, oxygen, and the halogens; although more generally the rule is applicable for the s-block and p-block of the periodic table. Other rules exist for other elements, such as the duplet rule for hydrogen and helium, and the 18-electron rule for transition metals. The valence electrons in molecules like carbon dioxide (CO₂) can be visualized using a Lewis electron dot diagram. In covalent bonds, electrons shared between two atoms are counted toward the octet of both atoms. In carbon dioxide each oxygen shares four electrons with the central carbon, two (shown in red) from the oxygen itself and two (shown in black) from the carbon. All four of these electrons are counted in both the carbon ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Proton NMR
Proton nuclear magnetic resonance (proton NMR, hydrogen-1 NMR, or 1H NMR) is the application of nuclear magnetic resonance in NMR spectroscopy with respect to hydrogen-1 nuclei within the molecules of a substance, in order to determine the structure of its molecules. In samples where natural hydrogen (H) is used, practically all the hydrogen consists of the isotope 1H (hydrogen-1; i.e. having a proton for a nucleus). Simple NMR spectra are recorded in solution, and solvent protons must not be allowed to interfere. Deuterated (deuterium = 2H, often symbolized as D) solvents especially for use in NMR are preferred, e.g. deuterated water, D2O, deuterated acetone, (CD3)2CO, deuterated methanol, CD3OD, deuterated dimethyl sulfoxide, (CD3)2SO, and deuterated chloroform, CDCl3. However, a solvent without hydrogen, such as carbon tetrachloride, CCl4 or carbon disulfide, CS2, may also be used. Historically, deuterated solvents were supplied with a small amount (typically 0.1%) of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
