|
Allylpalladium Chloride Dimer
Allylpalladium(II) chloride dimer (APC) is a chemical compound with the chemical formula, formula [(hapticity, η3-C3H5)PdCl]2. This yellow air-stable compound is an important catalyst used in organic synthesis.Tatsuno, Y.; Yoshida, T.; Otsuka, S. "(η3-allyl)palladium(II) Complexes" Inorganic Syntheses, 1990, volume 28, pages 342-345. It is one of the most widely used transition metal allyl complexes. Structure The compound has a dimeric structure that is Centrosymmetry, centrosymmetric. Each allyl group lies in a plane at an angle of about 111.5° to the square formed by the palladium and carbon atoms, and the Pd–C distances are all equal. Its unit cell is monoclinic. Synthesis The compound is prepared by purging carbon monoxide through a methanolic aqueous solution of sodium tetrachloropalladate (prepared from palladium(II) chloride and sodium chloride), and allyl chloride. :2 Na2PdCl4 + 2 CH2=CHCH2Cl + 2 CO + 2&nbs ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chloroform
Chloroform, or trichloromethane, is an organic compound with formula C H Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to PTFE. It is also a precursor to various refrigerants. It is trihalomethane. It is a powerful anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested. Structure The molecule adopts a tetrahedral molecular geometry with C3v symmetry. Natural occurrence The total global flux of chloroform through the environment is approximately tonnes per year, and about 90% of emissions are natural in origin. Many kinds of seaweed produce chloroform, and fungi are believed to produce chloroform in soil. Abiotic processes are also believed to contribute to natural chloroform productions in soils although the mechanism is still unclear. Chloroform volatilizes readily from soil and surface water and undergoes degradation in air to produce phosgene, dichloromethane, formyl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Allyl Chloride
Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle. Production Laboratory scale Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting allyl alcohol with phosphorus trichloride.Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June 2000. Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride. Industrial scale Allyl chloride is produced by the chlorination of propylene. At low ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbenes
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. The term "carbene" may also refer to the specific compound , also called methylene, the parent hydride from which all other carbene compounds are formally derived. Carbenes are classified as either singlets or triplets, depending upon their electronic structure. Most carbenes are very short lived, although persistent carbenes are known. One well-studied carbene is dichlorocarbene , which can be generated ''in situ'' from chloroform and a strong base. Structures and bonding The two classes of carbenes are singlet and triplet carbenes. Singlet carbenes are spin-paired. In the language of valence bond theory, the molecule adopts an sp2 hybrid structure. Triplet carbenes have two unpaired electrons. Most carbenes have a nonlinear triplet ground st ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diazo Compounds
The diazo group is an organic moiety consisting of two linked nitrogen atoms ( azo) at the terminal position. Overall charge neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds or diazoalkanes and are described by the general structural formula R2C=N+=N–. The simplest example of a diazo compound is diazomethane, CH2N2. Diazo compounds (R2C=N2) should not be confused with azo compounds of the type R-N=N-R or with diazonium compounds of the type R-N2+. Structure The electronic structure of diazo compounds is characterized by π electron density delocalized over the α-carbon and two nitrogen atoms, along with an orthogonal π system with electron density delocalized over only the terminal nitrogen atoms. Because all octet rule-satisfying resonance forms of diazo compounds have formal charges, they are members of a class of compounds known as 1,3-dipoles. Some of the most stable diazo compounds are α-diazo-β-diketones and ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diene
In organic chemistry a diene ( ) (diolefin ( ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nomenclature. As a subunit of more complex molecules, dienes occur in naturally occurring and synthetic chemicals and are used in organic synthesis. Conjugated dienes are widely used as monomers in the polymer industry. Polyunsaturated fats are of interest to nutrition. Classes Dienes can be divided into three classes, depending on the relative location of the double bonds: #Cumulated dienes have the double bonds sharing a common atom. The result is more specifically called an allene. #Conjugated dienes have conjugated double bonds separated by one single bond. Conjugated dienes are more stable than other dienes because of resonance. #Unconjugated dienes have the double bonds separated by two or more single bonds. They are usually less stable than ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nucleophilic Addition
In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions differ from electrophilic additions in that the former reactions involve the group to which atoms are added accepting electron pairs, whereas the latter reactions involve the group donating electron pairs. Addition to carbon–heteroatom double bonds Nucleophilic addition reactions of nucleophiles with electrophilic double or triple bond (π bonds) create a new carbon center with two additional single, or σ, bonds.March Jerry; (1985). Advanced Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc. Addition of a nucleophile to carbon–heteroatom double or triple bonds such as >C=O or -C≡N show great variety. These types of bonds are polar (have a large difference in electronegativity bet ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cross-coupling
In organic chemistry, a cross-coupling reaction is a reaction where two fragments are joined together with the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M (R = organic fragment, M = main group center) reacts with an organic halide of the type R'-X with formation of a new carbon–carbon bond in the product R-R'. Cross-coupling reaction are a subset of coupling reactions. It is often used in arylations. Richard F. Heck, Ei-ichi Negishi, and Akira Suzuki were awarded the 2010 Nobel Prize in Chemistry for developing palladium-catalyzed coupling reactions. Mechanism The mechanism generally involves reductive elimination of the organic substituents R and R' on a metal complex of the type LnMR(R') (where L is some arbitrary spectator ligand). The crucial intermediate LnMR(R') is formed in a two step process from a low valence precursor Ln. The oxidative addition of an organic halide (RX) to LnM gives LnMR(X). Subseq ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide. Properties Physical properties The molecular electric dipole moment is 2.2 debyes. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1. The standard enthalpy of formation is 100.2 kJ·mol−1 in the l ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclopentadienyl Allyl Palladium
Cyclopentadienyl allyl palladium is an organopalladium compound with formula (C5H5)Pd(C3H5). This reddish solid is volatile with an unpleasant odor. It is soluble in common organic solvents. The molecule consists of a Pd centre sandwiched between a Cp and allyl ligands. Preparation This complex is produced by the reaction of allylpalladium chloride dimer with sodium cyclopentadienide: :2 C5H5Na + (C3H5)2Pd2Cl2 → 2 (C5H4)Pd(C3H5) + 2 NaCl Structure and reactions The 18-electron complex adopts a half-sandwich structure with Cs symmetry, i.e., the molecule has a plane of symmetry. The complex can be decomposed readily by reductive elimination. :C3H5PdC3H5 → Pd(0) + C5H5C3H5 The compound readily reacts with alkyl isocyanides to produce clusters with the approximate formula d(CNR)2sub>n. It reacts with bulky alkyl phosphines to produce two-coordinated palladium(0) complexes: :CpPd(allyl) + 2 PR3 → Pd(PR3)2 + C5H5C3H5 The compound has been used to deposit thin film chem ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cyclopentadienyl Anion
In chemistry, the cyclopentadienyl anion or cyclopentadienide is an aromatic species with a formula of and abbreviated as Cp−. It is formed from the deprotonation of the molecule cyclopentadiene. Properties The cyclopentadienyl anion is a planar, cyclic, regular-pentagonal ion; it has 6 π-electrons (4''n'' + 2, where ''n'' = 1), which fulfills Hückel's rule of aromaticity. The structure shown is a composite of five resonance contributors in which each carbon atom carries part of the negative charge. Salts of the cyclopentadienyl anion can be stable, e.g., sodium cyclopentadienide. It can also coordinate as a ligand to metal atoms, forming coordination compounds known as cyclopentadienyl complexes. Biscyclopentadienyl complexes are called metallocenes. Cyclopentadienyl, , and cyclopentadiene, , can substitute one or more hydrogens, forming derivatives having covalent bonds. (See Cyclopentadiene#Derivatives) Abbreviation The abbreviation Cp for ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
