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Aryldiazonium Salt
Benzenediazonium tetrafluoroborate is an organic compound with the formula 6H5N2F4. It is a salt of a diazonium cation and tetrafluoroborate. It exists as a colourless solid that is soluble in polar solvents. It is the parent member of the aryldiazonium compounds, which are widely used in organic chemistry. Synthesis Diazotization of aniline: : C6H5NH2 + HNO2 (from NaNO2 and HCl) + HCl → 6H5N2l + 2 H2O The tetrafluoroborate can be obtained from crude benzenediazonium chloride by salt metathesis using tetrafluoroboric acid. : 6H5N2l + HBF4 → 6H5N2F4 + HCl The tetrafluoroborate is more stable than the chloride. Properties The diazo group (N2) can be replaced by many other groups, usually anions, giving a variety of substituted phenyl derivatives: :C6H5N2+ + Nu− → C6H5Nu + N2 These transformations are associated with many named reactions including the Schiemann reaction, Sandmeyer reaction, and Gomberg–Bachmann reaction. A wide range of groups that can be used ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-containing compounds such as alkanes (e.g. methane ) and its derivatives are universally considered organic, but many others are sometimes considered inorganic, such as certain compounds of carbon with nitrogen and oxygen (e.g. cyanide ion , hydrogen cyanide , chloroformic acid , carbon dioxide , and carbonate ion ). Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, and even ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chemical Formula
A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as parentheses, dashes, brackets, commas and ''plus'' (+) and ''minus'' (−) signs. These are limited to a single typographic line of symbols, which may include subscripts and superscripts. A chemical formula is not a chemical name since it does not contain any words. Although a chemical formula may imply certain simple chemical structures, it is not the same as a full chemical structural formula. Chemical formulae can fully specify the structure of only the simplest of molecules and chemical substances, and are generally more limited in power than chemical names and structural formulae. The simplest types of chemical formulae are called '' empirical formulae'', which use letters and numbers indicating the numerical ''proportions'' of atoms ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diazonium Compound
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, compound where R is hydrogen, is diazenylium. Structure and general properties Arene derivatives According to X-ray crystallography the linkage is linear in typical diazonium salts. The bond distance in benzenediazonium tetrafluoroborate is 1.083(3) Angstrom, Å, which is almost identical to that for dinitrogen molecule (N≡N). The linear free energy constants σm and σp indicate that the diazonium group is strongly electron-withdrawing. Thus, the diazonio-substituted phenols and benzoic acids have greatly reduced p''K''a values compared to their unsubstituted counterparts. The p''K''a of phenolic proton of 4-hydroxybenzenediazonium is 3.4, versus 9.9 for phenol itself. In other words, the diazonium group raises the ionization constant ... [...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 conv ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diazotization
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent, compound where R is hydrogen, is diazenylium. Structure and general properties Arene derivatives According to X-ray crystallography the linkage is linear in typical diazonium salts. The bond distance in benzenediazonium tetrafluoroborate is 1.083(3) Å, which is almost identical to that for dinitrogen molecule (N≡N). The linear free energy constants σm and σp indicate that the diazonium group is strongly electron-withdrawing. Thus, the diazonio-substituted phenols and benzoic acids have greatly reduced p''K''a values compared to their unsubstituted counterparts. The p''K''a of phenolic proton of 4-hydroxybenzenediazonium is 3.4, versus 9.9 for phenol itself. In other words, the diazonium group raises the ionization constant ''K''a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans. Relative to benzene, aniline is "electron-rich". It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone to oxidation: while freshly purified aniline is an almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the formation of strongly colored, oxidized impurities. Ani ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tetrafluoroboric Acid
Fluoroboric acid or tetrafluoroboric acid (archaically, fluoboric acid) is an inorganic compound with the simplified chemical formula . Solvent-free tetrafluoroboric acid () has not been reported. The term "fluoroboric acid" usually refers to a range of compounds including hydronium tetrafluoroborate (), which are available as solutions. The ethyl ether solvate is also commercially available, where the fluoroboric acid can be represented by the formula , where ''n'' is 2. It is mainly produced as a precursor to other fluoroborate salts.Gregory K. Friestad, Bruce P. Branchaud "Tetrafluoroboric Acid" E-Eros Encyclopedia of Reagents for Organic Synthesis. It is a strong acid. Fluoroboric acid is corrosive and attacks the skin. It is available commercially as a solution in water and other solvents such as diethyl ether. It is a strong acid with a weakly coordinating, non-oxidizing conjugate base. It is structurally similar to perchloric acid, but lacks the hazards associated with o ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Named Reaction
A name reaction (or named reaction) is a chemical reaction named after its discoverer(s) or developer(s). Among the tens of thousands of organic reactions that are known, hundreds of such reactions are typically identified by the eponym. Well-known examples include the Grignard reaction, the Sabatier reaction, the Wittig reaction, the Claisen condensation, the Friedel–Crafts acylation, and the Diels–Alder reaction. Books have been published devoted exclusively to name reactions;Alfred Hassner, C. Stumer. ''Organic syntheses based on name reactions''. Elsevier, 2002. Li, Jie Jack. ''Name Reactions: A Collection of Detailed Reaction Mechanisms''. Springer, 2003. the ''Merck Index'', a chemical encyclopedia, also includes an appendix on name reactions. As organic chemistry developed during the 20th century, chemists started associating synthetically useful reactions with the names of their discoverers or developers. In many cases, the name is merely a mnemonic. Some reactions suc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Schiemann Reaction
Schiemann is a surname. Notable people with the surname include: * Elisabeth Schiemann (1881–1972), German geneticist, crop researcher and resistance fighter in the Third Reich *Konrad Schiemann Sir Konrad Hermann Theodor Schiemann, PC (born 15 September 1937) is a former German-British barrister and judge. He served on the Court of Appeal, and he was also a member of the Court of Justice of the European Union. Schiemann was born in Ber ..., PC (born 1937), British barrister and judge * Paul Schiemann (1876–1944), Baltic German journalist, editor and politician known for his commitment to minority rights * Peter Schiemann (c.1980–2005), police officer killed in the Mayerthorpe tragedy on March 3, 2005 in the Canadian province of Alberta See also * Balz-Schiemann reaction, converts a primary aromatic amine to an aryl fluoride via a diazonium tetrafluorofluoroborate intermediate * Scheidemann * {{surname ... [...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. : The most commonly employed Sandmeyer reactions are the chlorination, bromination, cyanation, and hydroxylation reaction ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Gomberg–Bachmann Reaction
The Gomberg–Bachmann reaction, named for the Russian-American chemist Moses Gomberg and the American chemist Werner Emmanuel Bachmann, is an aryl-aryl coupling reaction via a diazonium salt. : The arene compound (here benzene) is reacted with a diazonium salt in the presence of a base to provide the biaryl through an intermediate aryl radical. For example, ''p''-bromobiphenyl may be prepared from 4-bromoaniline and benzene: : BrC6H4NH2 + C6H6 → BrC6H4−C6H5 The reaction offers a wide scope for both diazonium component and arene component but yields are generally low following the original procedure (less than 40%), given the many side-reactions of diazonium salts. Several improvements have been suggested. One possibility is to employ diazonium tetrafluoroborates in arene solvent together with a phase-transfer catalyst, another is to use 1-aryl-3,3-dialkyltriazenes. Pschorr reaction One intramolecular variation which gives better results is the Pschorr cyclization: : ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Azo Coupling
In organic chemistry, an azo coupling is an organic reaction, reaction between a diazonium compound () and another aromatic compound that produces an azo compound (). In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile, and the activating group, activated carbon (usually from an arene, which is called coupling agent), serves as a nucleophile. Classical coupling agents are phenols and naphthols. Usually the diazonium reagent attacks at the para position of the coupling agent. When the para position is occupied, coupling occurs at a ortho position, albeit at a slower rate. Uses of the reaction Aromatic azo compounds tend to be brightly colored due to their extended Conjugated system, conjugated systems. Many are useful dyes (see azo dye). Important azo dyes include methyl red and pigment red 170. Azo printing exploits this reaction as well. In this case, the diazonium ion is degraded by light, leaving a latent image in undegrade ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
