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Acylium Ions
In organic chemistry, acylium ions are cations with the formula RCO+, where R = alkyl or aryl. They are a kind of carbocation. Structure, bonding, synthesis In acylium ions, the C-C-O linkage is linear. The oxygen and the central carbon can be described as sp hybridized. A triple bond exists between C and O. Acylium ions can be viewed as C-alkylated derivatives of carbon monoxide (which also has a C-O triple bond). They are typically prepared by removal of chloride from acyl chlorides using strong Lewis acids such as antimony pentachloride. Several acylium salts have been characterized by X-ray crystallography, including the propionyl and mesityl derivatives. Because acylium cation is highly electrophilic, its salts can only be isolated with weakly coordinating anions. : Acetyl hexafluoroantimonate and hexachloroantimonate are other early examples. The strength of the bond is indicated by the frequency of its vibration (νCO). These values are 2300 and 2200 cm−1, ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic matter, organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes Physical property, physical and Chemical property, chemical properties, and evaluation of Reactivity (chemistry), chemical reactivity to understand their behavior. The study of organic reactions includes the organic synthesis, chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical (in silico) study. The range of chemicals studied chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Electrophile
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively Electric charge, charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through Addition reaction, addition and Substitution reaction, substitution reactions. Frequently seen electrophiles in Organic synthesis, organic syntheses include cations such as Hydrogen ion, H+ and nitrosonium, NO+, polarized neutral molecules such as hydrogen chloride, HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as chlorine, Cl2 and bromine, Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and Radical (chemistry), radicals, and some Lewis acids such as Borane, BH3 and Di ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbocations
Carbocation is a general term for ions with a positively charged carbon atom. In the present-day definition given by the IUPAC, a carbocation is any even-electron cation with significant partial positive charge on a carbon atom. They are further classified in two main categories according to the coordination number of the charged carbon: three in the carbenium ions and five in the carbonium ions. Among the simplest carbocations are the methenium (a carbenium ion), methanium (a carbonium ion), acylium ions , and vinyl cations. Until the early 1970s, carbocations were called ''carbonium ions''. This nomenclature was proposed by G. A. Olah. Carbonium ions, as originally defined by Olah, are characterized by a three-center two-electron delocalized bonding scheme and are essentially synonymous with so-called ' non-classical carbocations', which are carbocations that contain bridging C–C or C–H σ-bonds. However, others have more narrowly defined the term 'carbonium ion ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cations
An ion () is an atom or molecule with a net electrical charge. The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by convention. The net charge of an ion is not zero because its total number of electrons is unequal to its total number of protons. A cation is a positively charged ion with fewer electrons than protons (e.g. K+ ( potassium ion)) while an anion is a negatively charged ion with more electrons than protons (e.g. Cl− ( chloride ion) and OH− (hydroxide ion)). Opposite electric charges are pulled towards one another by electrostatic force, so cations and anions attract each other and readily form ionic compounds. Ions consisting of only a single atom are termed ''monatomic ions'', ''atomic ions'' or ''simple ions'', while ions consisting of two or more atoms are termed polyatomic ions or ''molecular ions''. If only a + or − is present, it indica ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Koch Carbonylation
The Koch reaction is an organic reaction for the synthesis of tertiary carboxylic acids from alcohols or alkenes and carbon monoxide. Some commonly industrially produced Koch acids include pivalic acid, 2,2-dimethylbutyric acid and 2,2-dimethylpentanoic acid. The Koch reaction employs carbon monoxide as a reagent and can therefore be classified as a carbonylation. The carbonylated product is converted to a carboxylic acid, so in this respect the Koch reaction can also be classified as a carboxylation. Substrate scope and applications Pivalic acid is produced from isobutene using the Koch reaction, as well as several other branched carboxylic acids. An estimated 150,000 tonnes of "Koch acids" and their derivatives annually.Weissermel, K., Jargen-Arpe, H. In "Syntheses involving carbon monoxide", ''Industrial Organic Chemistry''; VCH Publishers: New York, NY; pp. 141–145. () Koch–Haaf-type reactions have been used to carboxylate adamantanes. Conditions The reaction is a s ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pivaloyl Chloride
2,2-Dimethylpropanoyl chloride is a branched-chain acyl chloride. It was first made by Aleksandr Butlerov in 1874 by reacting pivalic acid with phosphorus pentachloride Phosphorus pentachloride is the chemical compound with the formula . It is one of the most important phosphorus chlorides/oxychlorides, others being and . finds use as a chlorinating reagent. It is a colourless, water-sensitive solid, althoug .... Pivaloyl chloride is used as an input in the manufacture of some drugs, insecticides and herbicides. References Acyl chlorides Reagents for organic chemistry {{organic-chem-stub ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrachloroaluminate
Tetrachloroaluminate lCl4sup>− is an anion formed from aluminium and chlorine. The anion has a tetrahedral shape and is isoelectronic with silicon tetrachloride. Some tetrachloroaluminates are soluble in organic solvents, creating an ionic non-aqueous solution, making them suitable as component of electrolytes for batteries. For example, lithium tetrachloroaluminate is used in some lithium batteries. Formation Tetrachloroaluminate ions are formed as intermediates in the Friedel–Crafts reactions when aluminium chloride is used as the catalyst. In the case of the Friedel –Crafts alkylation, the reaction can be broken into three steps as follows: # The alkyl halide reacts with the strong Lewis acid to form an activated electrophile composed of the tetrachloroaluminate ion and the alkyl group. #: # The aromatic ring (benzene in this case) reacts with the activated electrophile forming an alkylbenzenium carbocation. #: # The alkylbenzenium carbocation reacts with a tetr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aluminium Trichloride
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms a hexahydrate with the formula , containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are colourless crystals, but samples are often contaminated with iron(III) chloride, giving them a yellow colour. The anhydrous form is commercially important. It has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium, but large amounts are also used in other areas of the chemical industry. The compound is often cited as a Lewis acid. It is an inorganic compound that reversibly changes from a polymer to a monomer at mild temperature. Structure Anhydrous adopts three structures, depending on the temperature and the state (solid, liquid, gas). Solid has a sheet-like layered structure with cubic close-packed chloride ions. In this framework, the Al centres exhibit octahedral coordination geome ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetyl Chloride
Acetyl chloride () is an acyl chloride derived from acetic acid (). It belongs to the class of organic compounds called acid halides. It is a colorless, corrosive, volatile liquid. Its formula is commonly abbreviated to AcCl. Synthesis On an industrial scale, the reaction of acetic anhydride with hydrogen chloride produces a mixture of acetyl chloride and acetic acid: : Laboratory routes Acetyl chloride was first prepared in 1852 by French chemist Charles Gerhardt by treating potassium acetate with phosphoryl chloride. Acetyl chloride is produced in the laboratory by the reaction of acetic acid with chlorodehydrating agents such as phosphorus trichloride (), phosphorus pentachloride (), sulfuryl chloride (), phosgene, or thionyl chloride (). However, these methods usually give acetyl chloride contaminated by phosphorus or sulfur impurities, which may interfere with the organic reactions. Other methods When heated, a mixture of dichloroacetyl chloride and acetic aci ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Arene
Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were understood. The current definition of aromatic compounds does not have any relation to their odor. Aromatic compounds are now defined as cyclic compounds satisfying Hückel's rule. Aromatic compounds have the following general properties: * Typically unreactive * Often non polar and hydrophobic * High carbon-hydrogen ratio * Burn with a strong sooty yellow flame, due to high C:H ratio * Undergo electrophilic substitution reactions and nucleophilic aromatic substitutions Arenes are typically split into two categories - benzoids, that contain a benzene derivative and follow the benzene ring model, and non-benzoids that contain other aromatic cyclic derivatives. Aromatic compounds are commonly used in organic synthesis and are involved i ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexachloroantimonate
Antimony pentachloride is a chemical compound with the formula SbCl5. It is a colourless oil, but typical samples are yellowish due to dissolved chlorine. Owing to its tendency to hydrolyse to hydrochloric acid, SbCl5 is a highly corrosive substance and must be stored in glass or PTFE containers. Preparation and structure Antimony pentachloride is prepared by passing chlorine gas into molten antimony trichloride: :SbCl3 + Cl2 → SbCl5 Gaseous SbCl5 has a trigonal bipyramidal structure. Reactions This compounds reacts with water to form antimony pentoxide and hydrochloric acid: :2 SbCl5 + 5 H2O → Sb2O5 + 10 HCl The mono- and tetrahydrates are known, SbCl5·H2O and SbCl5·4H2O. This compound forms adducts with many Lewis bases. SbCl5 is a soft Lewis acid and its ECW model parameters are EA = 3.64 and CA = 10.42. It is used as the standard Lewis acid in the Gutmann scale of Lewis basicity. It is also a strong oxidizing agent. For example aromatic ethers are oxidized to ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
