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Organoboron Chemistry
Organoboron chemistry or organoborane chemistry studies organoboron compounds, also called organoboranes. These chemical compounds combine boron and carbon; typically, they are organic derivatives of borane (BH3), as in the trialkyl boranes. Organoboranes and -borates enable many chemical transformations in organic chemistry — most importantly, hydroboration and carboboration. Most reactions transfer a nucleophilic boron substituent to an electrophilic center either inter- or intramolecularly. In particular, α,β-unsaturated borates and borates with an α leaving group are highly susceptible to intramolecular 1,2-migration of a group from boron to the electrophilic α position. Oxidation or protonolysis of the resulting organoboranes generates many organic products, including alcohols, carbonyl compounds, alkenes, and halides. Properties of the B-C bond The C-B bond has low polarity (electronegativity 2.55 for carbon and 2.04 for boron). Alkyl boron compounds are ... [...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] |
Borane Dimethyl Sulfide
Borane dimethylsulfide (BMS) is a chemical compound with the chemical formula . It is an adduct between borane molecule () and dimethyl sulfide molecule (). It is a complexed borane reagent that is used for hydroborations and reductions. The advantages of BMS over other borane reagents, such as borane-tetrahydrofuran, are its increased stability and higher solubility. BMS is commercially available at much higher concentrations than its tetrahydrofuran counterpart (10 M) and does not require sodium borohydride as a stabilizer, which could result in undesired side reactions. In contrast, Borane–tetrahydrofuran, requires sodium borohydride to inhibit reduction of THF to tributyl borate (). BMS is soluble in most aprotic solvents. Preparation and structure Although usually purchased, BMS can be prepared by absorbing diborane into dimethyl sulfide: : It can be purified by bulb to bulb vacuum transfer. Although a structure of BMS has not been determined crystallographically, (pe ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetramethylethylene
Tetramethylethylene is a hydrocarbon with the formula Me2C=CMe2 (Me = methyl). A colorless liquid, it is the simplest tetrasubstituted alkene. Synthesis It can be prepared by base-catalyzed isomerization of 2,3-dimethyl-1-butene. Another route involves direct dimerization of propylene. It can also be produced by photolysis of tetramethylcyclobutane-1,3-dione. Reactions Tetramethylethylene forms metal-alkene complexes with low-valent metals and reacts with diborane to give the monoalkyborane known as thexylborane Thexylborane is a borane with the formula e2CHCMe2BH2sub>2 (Me = methyl). The name derives from "''t''-hexylborane" (although the group is not the standard ''tert''-hexyl group), and the formula is often abbreviated ThxBH2. A colorless liquid, ....{{cite book, doi=10.1002/9780470132593.ch22, title=Di-μ-Chloro-Bis(η4-1,5-Cyclooctadiene)-Dirhodium(I), series=Inorganic Syntheses, pages=88–90, year=1990, volume=28, last1=Giordano, first1=G., last2=Crabtree, fir ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Thexylborane
Thexylborane is a borane with the formula e2CHCMe2BH2sub>2 (Me = methyl). The name derives from "''t''-hexylborane" (although the group is not the standard ''tert''-hexyl group), and the formula is often abbreviated ThxBH2. A colorless liquid, it is a monoalkylborane. It is produced by the hydroboration of tetramethylethylene: :B2H6 + 2 Me2C=CMe2 → e2CHCMe2BH2sub>2 Reactions Thexylborane is generated ''in situ is a Latin phrase meaning 'in place' or 'on site', derived from ' ('in') and ' ( ablative of ''situs'', ). The term typically refers to the examination or occurrence of a process within its original context, without relocation. The term is use ...''. In solution, it isomerizes over the course several days to the 2,3-dimethyl-1-butyl derivative, shown as the monomer here: :Me2CHCMe2BH2 → Me2CHCH(Me)CH2BH2 Thexylborane allows the synthesis of ketones by coupling a pair of alkenes with carbon monoxide, which serves as a carbonyl linchpin: :Me2CHCMe2BH2 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Redistribution Reaction
In chemistry, redistribution usually refers to the exchange of anionic ligands bonded to metal and metalloid centers. The conversion does not involve redox Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is t ..., in contrast to disproportionation reactions. Some useful redistribution reactions are conducted at higher temperatures; upon cooling the mixture, the product mixture is kinetically frozen and the individual products can be separated. In cases where redistribution is rapid at mild temperatures, the reaction is less useful synthetically but still important mechanistically. Examples Redistribution reactions are exhibited by methylboranes. Thus monomethyldiborane rapidly converts at room temperature to diborane and trimethylborane:. The authors refer to redistributions as "dis ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Trigonal Planar Molecular Geometry
In chemistry, trigonal planar is a molecular geometry model with one atom at the center and three atoms at the corners of an equilateral triangle, called peripheral atoms, all in one plane. In an ideal trigonal planar species, all three ligands are identical and all bond angles are 120°. Such species belong to the point group D3h. Molecules where the three ligands are not identical, such as H2CO, deviate from this idealized geometry. Examples of molecules with trigonal planar geometry include boron trifluoride (BF3), formaldehyde (H2CO), phosgene (COCl2), and sulfur trioxide (SO3). Some ions with trigonal planar geometry include nitrate (), carbonate (), and guanidinium (). In organic chemistry, planar, three-connected carbon centers that are trigonal planar are often described as having sp2 hybridization. Nitrogen inversion is the distortion of pyramidal amines through a transition state that is trigonal planar. Pyramidalization is a distortion of this molecular shape towa ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triethylboron
Triethylborane (TEB), also called triethylboron, is an organoborane (a compound with a B–C bond). It is a colorless pyrophoric liquid. Its chemical formula is or , abbreviated . It is soluble in organic solvents tetrahydrofuran and hexane. Preparation and structure Triethylborane is prepared by the reaction of trimethyl borate with triethylaluminium: :Et3Al + (MeO)3B → Et3B + (MeO)3Al The molecule is monomeric, unlike H3B and Et3Al, which tend to dimerize. It has a planar BC3 core. Applications Turbojet engines Triethylborane was used to ignite the JP-7 fuel in the Pratt & Whitney J58 turbojet/ramjet engines powering the Lockheed SR-71 Blackbird and its predecessor, the A-12 OXCART. Triethylborane is suitable because it ignites readily upon exposure to oxygen. It was chosen as an ignition method for reliability reasons, and in the case of the Blackbird, because JP-7 fuel has very low volatility and is difficult to ignite. Conventional ignition plugs posed a high risk of m ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lewis Acid
A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons. Trimethylborane CH3)3Bis a Lewis acid as it is capable of accepting a lone pair. In a Lewis adduct, the Lewis acid and base share an electron pair furnished by the Lewis base, forming a dative bond. In the context of a specific chemical reaction between NH3 and Me3B, a lone pair from NH3 will form a dative bond with the empty orbital of Me3B to form an adduct NH3•BMe3. The terminology refers to the contributions of Gilbert N. Lewis. From p. 142: "We are inclined to think of substances as ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diborane
Diborane(6), commonly known as diborane, is the chemical compound with the formula . It is a highly toxic, colorless, and pyrophoric gas with a repulsively sweet odor. Given its simple formula, borane is a fundamental boron compound. It has attracted wide attention for its electronic structure. Several of its derivatives are useful reagents. Structure and bonding The structure of diborane has D2h symmetry. Four hydrides are terminal, while two bridge between the boron centers. The lengths of the B–Hbridge bonds and the B–Hterminal bonds are 1.33 and 1.19 Å respectively. This difference in bond lengths reflects the difference in their strengths, the B–Hbridge bonds being relatively weaker. The weakness of the B–Hbridge compared to B–Hterminal bonds is indicated by their vibrational signatures in the infrared spectrum, being ≈2100 and 2500 cm−1 respectively. The model determined by molecular orbital theory describes the bonds between boron and the te ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ar2BHmonomer
AR, Ar, or A&R may refer to: Arts, entertainment, and media Music * Artists and repertoire * ''AR'' (EP), the debut EP by Addison Rae Periodicals * ''Absolute Return + Alpha'', a hedge fund publication *''The Adelaide Review'', an Australian arts magazine * ''American Renaissance'' (magazine), a white nationalist magazine and website * ''Architectural Review'', a British architectural journal * '' Armeerundschau'', a magazine of the East German army Other media * Ar, city on the fictional planet Gor * A.r. group, an avant-garde art group * Alternate reality (other), various fictional concepts Business * Accounts receivable, abbreviated as AR or A/R * Acoustic Research, an American audio electronics manufacturer * Aerojet Rocketdyne, an American aerospace and defense manufacturer * Aerolíneas Argentinas (IATA airline code AR) * AtkinsRéalis, Canadian engineering company * Some Alfa Romeo car models, e.g. AR51 * Toyota AR engine Language * ''Ar'', the Latin let ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Double Bond
In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist between two different elements: for example, in a carbonyl group between a carbon atom and an oxygen atom. Other common double bonds are found in azo compounds (N=N), imines (C=N), and sulfoxides (S=O). In a skeletal formula, a double bond is drawn as two parallel lines (=) between the two connected atoms; typographically, the equals sign is used for this. Double bonds were introduced in chemical notation by Russian chemist Alexander Butlerov. Double bonds involving carbon are stronger and shorter than single bonds. The bond order is two. Double bonds are also electron-rich, which makes them potentially more reactive in the presence of a strong electron acceptor (as in addition reactions of the halogens). File:Ethene structural.svg, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
