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Balz–Schiemann Reaction
The Balz–Schiemann reaction (also called the Schiemann reaction) is a chemical reaction in which a primary aromatic amine is transformed to an aryl fluoride via a diazonium tetrafluoroborate intermediate. This reaction is a traditional route to fluorobenzene and some related derivatives, including 4-fluorobenzoic acid. : The reaction is conceptually similar to the Sandmeyer reaction, which converts diazonium salts to other aryl halides (ArCl, ArBr). However, while the Sandmeyer reaction involves a copper reagent/catalyst and radical intermediates, the thermal decomposition of the diazonium tetrafluoroborate proceeds without a promoter and is believed to generate highly unstable aryl cations (Ar+), which abstract F− from BF4− to give the fluoroarene (ArF), along with boron trifluoride as the byproduct. Innovations The traditional Balz–Schiemann reaction employs HBF4 and involves isolation of the diazonium salt. Both aspects can be profitably modified. Other counterion ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrafluoroborate
Tetrafluoroborate is the anion . This tetrahedral species is isoelectronic with tetrafluoroberyllate (), tetrafluoromethane (CF4), and tetrafluoroammonium () and is valence isoelectronic with many stable and important species including the perchlorate anion, , which is used in similar ways in the laboratory. It arises by the reaction of fluoride salts with the Lewis acid BF3, treatment of tetrafluoroboric acid with base, or by treatment of boric acid with hydrofluoric acid. As an anion in inorganic and organic chemistry The popularization of has led to decreased use of in the laboratory as a weakly coordinating anion. With organic compounds, especially amine derivatives, forms potentially explosive derivatives. Disadvantages to include its slight sensitivity to hydrolysis and decomposition via loss of a fluoride ligand, whereas does not suffer from these problems. Safety considerations, however, overshadow this inconvenience. With a formula weight of 86.8, BF is also conveni ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Halogenation Reactions
In chemistry, halogenation is a chemical reaction that entails the introduction of one or more halogens into a compound. Halide-containing compounds are pervasive, making this type of transformation important, e.g. in the production of polymers, drugs. This kind of conversion is in fact so common that a comprehensive overview is challenging. This article mainly deals with halogenation using elemental halogens (F2, Cl2, Br2, I2). Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for and introducing halogens into diverse substrates, e.g. thionyl chloride. Organic chemistry Several pathways exist for the halogenation of organic compounds, including free radical halogenation, ketone halogenation, electrophilic halogenation, and halogen addition reaction. The nature of the substrate determines the pathway. The facility of halogenation is influenced by the halogen. Fluorine and chlorine are more electrophilic and are m ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nitrosonium
The nitrosonium ion is , in which the nitrogen atom is bonded to an oxygen atom with a bond order of 3, and the overall diatomic species bears a positive charge. It can be viewed as nitric oxide with one electron removed. This ion is usually obtained as the following salts: , (nitrosylsulfuric acid, more descriptively written ) and . The and salts are slightly soluble in acetonitrile . NOBF4 can be purified by sublimation at 200–250 °C and . is isoelectronic with CO, and . It arises via protonation of nitrous acid: :HONO + H+ NO+ + H2O Chemical properties Hydrolysis reacts readily with water to form nitrous acid: : For this reason, nitrosonium compounds must be protected from water or even moist air. With base, the reaction generates nitrite: : As a diazotizing agent reacts with aryl amines, , to give diazonium salts, . The resulting diazonium group is easily displaced (unlike the amino group) by a variety of nucleophiles. As an oxidizing agent , e.g. as ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
The Journal Of Organic Chemistry
''The Journal of Organic Chemistry'', colloquially known as ''JOC'', is a peer-reviewed scientific journal for original contributions of fundamental research in all branches of theory and practice in organic and bioorganic chemistry. It is published by the publishing arm of the American Chemical Society, with 24 issues per year. According to the ''Journal Citation Reports'', the journal had a 2017 impact factor of 4.805 and it is the journal that received the most cites (100,091 in 2017) in the field of organic chemistry. According to Web of Knowledge (and as December 2012), eleven papers from the journal have received more than 1,000 citations, with the most cited paper having received 7,967 citations. The current editor-in-chief is Scott J. Miller from Yale University. Indexing ''J. Org. Chem.'' is currently indexed in: See also *Organic Letters *Organometallics ''Organometallics'' is a biweekly journal published by the American Chemical Society. Its area of focus is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexafluoroantimonate
Antimony pentafluoride is the inorganic compound with the formula Sb F5. This colourless, viscous liquid is a valuable Lewis acid and a component of the superacid fluoroantimonic acid, formed when mixing liquid HF with liquid SbF5 in a 2:1 ratio. It is notable for its Lewis acidity and its ability to react with almost all known compounds. Preparation Antimony pentafluoride is prepared by the reaction of antimony pentachloride with anhydrous hydrogen fluoride:Sabina C. Grund, Kunibert Hanusch, Hans J. Breunig, Hans Uwe Wolf "Antimony and Antimony Compounds" in Ullmann's Encyclopedia of Industrial Chemistry 2006, Wiley-VCH, Weinheim. :SbCl5 + 5 HF → SbF5 + 5 HCl It can also be prepared from antimony trifluoride and fluorine. Structure and chemical reactions In the gas phase, SbF5 adopts a trigonal bipyramidal structure of D3h point group symmetry (see picture). The material adopts a more complicated structure in the liquid and solid states. The liquid contains polymers wherein e ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hexafluorophosphate
Hexafluorophosphate is an anion with chemical formula of . It is an octahedral species that imparts no color to its salts. is isoelectronic with sulfur hexafluoride, , and the hexafluorosilicate dianion, , and hexafluoroantimonate . In this anion, phosphorus has a valence of 5. Being poorly nucleophilic, hexafluorophosphate is classified as a non-coordinating anion. Synthesis Hexafluorophosphate salts can be prepared by the reaction of phosphorus pentachloride and alkali or ammonium halide in a solution of hydrofluoric acid: : Hexafluorophosphoric acid can be prepared by direct reaction of hydrogen fluoride with phosphorus pentafluoride. It is a strong Brønsted acid that is typically generated ''in situ'' immediately before its use. : These reactions require specialized equipment to safely handle the hazards associated with hydrofluoric acid and hydrogen fluoride. Quantitative analysis Several methods of quantitative analysis for the hexafluorophosphate ion have been de ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Counterion
160px, Polystyrene sulfonate, a cation-exchange resin, is typically supplied with as the counterion.">cation-exchange_resin.html" ;"title="Polystyrene sulfonate, a cation-exchange resin">Polystyrene sulfonate, a cation-exchange resin, is typically supplied with as the counterion. In chemistry, a counterion (sometimes written as "counter ion", pronounced as such) is the ion that accompanies an Ionic compound, ionic species in order to maintain Electric charge, electric neutrality. In table salt (NaCl, also known as sodium chloride) the sodium ion (positively charged) is the counterion for the chloride ion (negatively charged) and vice versa. A counterion will be more commonly referred to as an anion or a cation, depending on whether it is negatively or positively charged. Thus, the counterion to an anion will be a cation, and vice versa. In biochemistry, counterions are generally vaguely defined. Depending on their charge, proteins are associated with a variety of smaller ani ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Boron Trifluoride
Boron trifluoride is the inorganic compound with the formula BF3. This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure and bonding The geometry of a molecule of BF3 is trigonal planar. Its D3h symmetry conforms with the prediction of VSEPR theory. The molecule has no dipole moment by virtue of its high symmetry. The molecule is isoelectronic with the carbonate anion, . BF3 is commonly referred to as " electron deficient," a description that is reinforced by its exothermic reactivity toward Lewis bases. In the boron trihalides, BX3, the length of the B–X bonds (1.30 Å) is shorter than would be expected for single bonds, and this shortness may indicate stronger B–X π-bonding in the fluoride. A facile explanation invokes the symmetry-allowed overlap of a p orbital on the boron atom with the in-phase combination of the three similarly oriented p orbitals ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aryl Halide
In organic chemistry, an aryl halide (also known as haloarene) is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications. Preparation The two main preparatory routes to aryl halides are direct halogenation and via diazonium salts. Direct halogenation In the Friedel-Crafts halogenation, Lewis acids serve as catalysts. Many metal chlorides are used, examples include iron(III) chloride or aluminium chloride. The most important aryl halide, chlorobenzene is produced by this route. Monochlorination of benzene is always accompanied by formation of the dichlorobenzene derivatives. Arenes with electron donating groups react with halogens even in the absence of Le ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aromatic Amine
In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses anilines, but also many more complex aromatic rings and many amine substituents beyond . Such compounds occur widely. Aromatic amines are widely used as precursor to pesticides, pharmaceuticals, and dyes. Aromatic amines in textiles Since August 2012, the new standard EN 14362-1:2012 ''Textiles - Methods for determination of certain aromatic amines derived from azo colorants - Part 1: Detection of the use of certain azo colorants accessible with and without extracting the fibres'' is effective. It had been officially approved by the European Committee for Standardization (CEN) and supersedes the test standards EN 14362-1: 2003 and EN 14362-2: 2003. The standard describes a procedure to detect EU banned aromatic amines derived from azo colorants in textile fibres, including natural, man-made, regenerated, and ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sandmeyer Reaction
The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts using copper salts as reagents or catalysts. It is an example of a radical-nucleophilic aromatic substitution. The Sandmeyer reaction provides a method through which one can perform unique transformations on benzene, such as halogenation, cyanation, trifluoromethylation, and hydroxylation. : The reaction was discovered in 1884 by Swiss chemist Traugott Sandmeyer, when he attempted to synthesize phenylacetylene from benzenediazonium chloride and copper(I) acetylide. Instead, the main product he isolated was chlorobenzene. In modern times, the Sandmeyer reaction refers to any method for substitution of an aromatic amino group via preparation of its diazonium salt followed by its displacement with a nucleophile in the presence of catalytic copper(I) salts. (Due to the low cost of copper salts, a stoichiometric amount is often employed for better reactivity even when catalysis is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
