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Thionyl Fluoride
Thionyl fluoride is the inorganic compound with the formula . This colourless gas is mainly of theoretical interest, but it is a product of the degradation of sulfur hexafluoride, an insulator in electrical equipment. The molecule adopts a distorted pyramidal structure, with Cs symmetry. The S-O and S-F distances are 1.42 and 1.58 Å, respectively. The O-S-F and F-S-F angles are 106.2 and 92.2°, respectively. Synthesis and reactions Thionyl fluoride can be produced by the reaction of thionyl chloride with fluoride sources such as antimony trifluoride. : Alternatively, it arises via the fluorination of sulfur dioxide: : Thionyl fluoride arises as a fleeting intermediate from the decomposition of sulfur hexafluoride as the result of electrical discharges which generate sulfur tetrafluoride. SF4 hydrolyzes to give thionyl fluoride, which in turn hydrolyzes further as described below. As expected from the behavior of the other thionyl halides, this compound hydrolyzes readily, g ...
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Thionyl Chloride
Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately Volatility (chemistry), volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a Halogenation, chlorinating reagent, with approximately per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also List of Schedule 3 substances (CWC), listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons. Thionyl chloride is sometimes confused with sulfuryl chloride, , but the properties of these compounds differ significantly. Sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions. Production The major industrial synthesis involves the reaction of sulfur trioxide and sulfur dichloride. This synthesis can be adapted to the laboratory by heating oleum to slowly distill the sulfur trioxide into a cooled fla ...
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Antimony Trifluoride
Antimony trifluoride is the inorganic compound with the formula SbF3. Sometimes called Swarts' reagent, it is one of two principal fluorides of antimony, the other being SbF5. It appears as a white solid. As well as some industrial applications, it is used as a reagent in inorganic and organofluorine chemistry. Preparation and structure In solid SbF3, the Sb centres have octahedral molecular geometry and are linked by bridging fluoride ligands. Three Sb–F bonds are short (192 pm) and three are long (261 pm). Because it is a polymer, SbF3 is far less volatile than related compounds AsF3 and SbCl3. SbF3 is prepared by treating antimony trioxide with hydrogen fluoride: :Sb2O3 + 6 HF → 2 SbF3 + 3 H2O The compound is a mild Lewis acid, hydrolyzing slowly in water. With fluorine, it is oxidized to give antimony pentafluoride. :SbF3 + F2 → SbF5 Applications It is used as a fluorination reagent in organic chemistry. This application was reported by the Belgian c ...
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Thionyl Compounds
The thionyl group is SO, a sulfur atom plus an oxygen atom. It occurs in compounds such as thionyl fluoride, SOF2. Thionyl chloride, SOCl2, is a common reagent used in organic synthesis to convert carboxylic acids to acyl chlorides. In 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 ..., the thionyl group is known as a sulfoxide group or sulfinyl group, and has the general structure RS(=O)R'. In the context of acid-base reactions, it may also be referred to as a sulfinyl group (i.e. sulfinylamines). See also * Sulfuryl References * Functional groups {{chem-compound-stub ...
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Halogenation
In chemistry, halogenation is a chemical reaction which introduces one or more halogens into a chemical 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 (). Halides are also commonly introduced using salts of the halides and halogen acids. Many specialized reagents exist for 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 more aggressive haloge ...
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Hydrogen Fluoride
Hydrogen fluoride (fluorane) is an Inorganic chemistry, inorganic compound with chemical formula . It is a very poisonous, colorless gas or liquid that dissolves in water to yield hydrofluoric acid. It is the principal industrial source of fluorine, often in the form of hydrofluoric acid, and is an important feedstock in the preparation of many important compounds including pharmaceuticals and polymers such as polytetrafluoroethylene (PTFE). HF is also widely used in the petrochemical industry as a component of superacids. Due to strong and extensive hydrogen bonding, it boils near room temperature, a much higher temperature than other hydrogen halides. Hydrogen fluoride is an extremely dangerous gas, forming corrosive and penetrating hydrofluoric acid upon contact with moisture. The gas can also cause blindness by rapid destruction of the corneas. History In 1771 Carl Wilhelm Scheele prepared the aqueous solution, hydrofluoric acid in large quantities, although hydrofluoric acid ...
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Sulfur Tetrafluoride
Sulfur tetrafluoride is a chemical compound with the formula S F4. It is a colorless corrosive gas that releases dangerous hydrogen fluoride gas upon exposure to water or moisture. Sulfur tetrafluoride is a useful reagent for the preparation of organofluorine compounds, some of which are important in the pharmaceutical and specialty chemical industries. Structure Sulfur in SF4 is in the +4 oxidation state, with one lone pair of electrons. The atoms in SF4 are arranged in a see-saw shape, with the sulfur atom at the center. One of the three equatorial positions is occupied by a nonbonding lone pair of electrons. Consequently, the molecule has two distinct types of F ligands, two axial and two equatorial. The relevant bond distances are = 164.3 pm and = 154.2 pm. It is typical for the axial ligands in hypervalent molecules to be bonded less strongly. The 19F NMR spectrum of SF4 reveals only one signal, which indicates that the axial and equatorial F ...
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Sulfur Dioxide
Sulfur dioxide (IUPAC-recommended spelling) or sulphur dioxide (traditional Commonwealth English) is the chemical compound with the formula . It is a colorless gas with a pungent smell that is responsible for the odor of burnt matches. It is released naturally by volcanic activity and is produced as a by-product of metals refining and the burning of Sour gas, sulfur-Sour crude oil, bearing fossil fuels. Sulfur dioxide is somewhat toxic to humans, although only when inhaled in relatively large quantities for a period of several minutes or more. It was known to medieval alchemy, alchemists as "volatile spirit of sulfur". Structure and bonding SO2 is a bent molecule with ''C''2v Point groups in three dimensions, symmetry point group. A valence bond theory approach considering just ''s'' and ''p'' orbitals would describe the bonding in terms of resonance (chemistry), resonance between two resonance structures. The sulfur–oxygen bond has a bond order of 1.5. There is support f ...
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SbCl3
Antimony trichloride is the chemical compound with the formula SbCl3. It is a soft colorless solid with a pungent odor and was known to alchemists as butter of antimony. Preparation Antimony trichloride is prepared by reaction of chlorine with antimony, antimony tribromide, antimony trioxide, or antimony trisulfide. It also may be made by treating antimony trioxide with concentrated hydrochloric acid. Reactions SbCl3 is readily hydrolysed and samples of SbCl3 must be protected from moisture. With a limited amount of water it forms antimony oxychloride releasing hydrogen chloride: :SbCl3 + H2O → SbOCl + 2 HCl With more water it forms which on heating to 460° under argon converts to . SbCl3 readily forms complexes with halides, but the stoichiometries are not a good guide to the composition; for example, the contains a chain anion with distorted SbIII octahedra. Similarly the salt contains a polymeric anion of composition with distorted octahedral SbIII. With nitrogen do ...
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SbF3
Antimony trifluoride is the inorganic compound with the formula SbF3. Sometimes called Swarts' reagent, it is one of two principal fluorides of antimony, the other being SbF5. It appears as a white solid. As well as some industrial applications, it is used as a reagent in inorganic and organofluorine chemistry. Preparation and structure In solid SbF3, the Sb centres have octahedral molecular geometry and are linked by bridging fluoride ligands. Three Sb–F bonds are short (192 pm) and three are long (261 pm). Because it is a polymer, SbF3 is far less volatile than related compounds AsF3 and SbCl3. SbF3 is prepared by treating antimony trioxide with hydrogen fluoride: :Sb2O3 + 6 HF → 2 SbF3 + 3 H2O The compound is a mild Lewis acid, hydrolyzing slowly in water. With fluorine, it is oxidized to give antimony pentafluoride. :SbF3 + F2 → SbF5 Applications It is used as a fluorination reagent in organic chemistry. This application was reported by the Belgian c ...
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Thionyl Chloride
Thionyl chloride is an inorganic compound with the chemical formula . It is a moderately Volatility (chemistry), volatile, colourless liquid with an unpleasant acrid odour. Thionyl chloride is primarily used as a Halogenation, chlorinating reagent, with approximately per year being produced during the early 1990s, but is occasionally also used as a solvent. It is toxic, reacts with water, and is also List of Schedule 3 substances (CWC), listed under the Chemical Weapons Convention as it may be used for the production of chemical weapons. Thionyl chloride is sometimes confused with sulfuryl chloride, , but the properties of these compounds differ significantly. Sulfuryl chloride is a source of chlorine whereas thionyl chloride is a source of chloride ions. Production The major industrial synthesis involves the reaction of sulfur trioxide and sulfur dichloride. This synthesis can be adapted to the laboratory by heating oleum to slowly distill the sulfur trioxide into a cooled fla ...
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Thionyl Bromide
Thionyl bromide is the chemical compound SOBr2. It is less stable and less widely used than its chloride analogue, thionyl chloride, but engages in similar reactions. Chemistry It is prepared by the action of hydrogen bromide on thionyl chloride, although the corresponding reaction at higher pH (i.e. alkali bromides) proceeds only with difficulty: :SOCl2 + 2 HBr → SOBr2 + 2 HCl Phosphorus trichlorodibromide (but not phosphorus pentabromide!) converts sulfur dioxide to thionyl bromide. Thionyl chlorobromide appears to be a key intermediate in these syntheses, but has not been isolated. Thionyl bromide will convert alcohols to alkyl bromides and carboxylic acids to acyl bromides. Unlike with thionyl chloride, stoichiometric bases are problematic activating agents, because free bromide anions decompose thionyl bromide to tribromide, sulfur dioxide, and sulfur. It can be used for brominations of certain α,β-unsaturated carbonyl compounds. It may occasionally be ...
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