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Sulfone
In organic chemistry, a sulfone is a organosulfur compound containing a sulfonyl () functional group attached to two carbon atoms. The central hexavalent sulfur atom is double-bonded to each of two oxygen atoms and has a single bond to each of two carbon atoms, usually in two separate hydrocarbon substituents. Synthesis and reactions By oxidation of thioethers and sulfoxides Sulfones are typically prepared by organic oxidation of thioethers, often referred to as sulfides. Sulfoxides are intermediates in this route. For example, dimethyl sulfide oxidizes to dimethyl sulfoxide and then to dimethyl sulfone. From SO2 : Sulfur dioxide is a convenient and widely used source of the sulfonyl functional group. Specifically, Sulfur dioxide participates in cycloaddition reactions with dienes. The industrially useful solvent sulfolane is prepared by addition of sulfur dioxide to buta-1,3-diene followed by hydrogenation of the resulting sulfolene. From sulfonyl and sulfuryl halides Sulf ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methylsulfonylmethane
Dimethyl sulfone (DMSO2) is an organosulfur compound with the formula . It is also known by several other names including methyl sulfone and (especially in alternative medicine) methylsulfonylmethane (MSM). This colorless solid features the sulfonyl functional group and is the simplest of the sulfones. It is relatively inert chemically and is able to resist decomposition at elevated temperatures. It occurs naturally in some primitive plants, is present in small amounts in many foods and beverages, and is marketed (under the MSM name) as a dietary supplement. It is sometimes used as a cutting agent for illicitly manufactured methamphetamine. It is also commonly found in the atmosphere above marine areas, where it is used as a carbon source by the airborne bacteria '' Afipia''. Oxidation of dimethyl sulfoxide produces the sulfone, both under laboratory conditions and metabolically. Use as a solvent Because of its polarity and thermal stability, molten DMSO2 has been used industria ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organosulfur Compound
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur derivatives, e.g., saccharin. Nature is abound with organosulfur compounds—sulfur is vital for life. Of the 20 common amino acids, two ( cysteine and methionine) are organosulfur compounds, and the antibiotics penicillin and sulfa drugs both contain sulfur. While sulfur-containing antibiotics save many lives, sulfur mustard is a deadly chemical warfare agent. Fossil fuels, coal, petroleum, and natural gas, which are derived from ancient organisms, necessarily contain organosulfur compounds, the removal of which is a major focus of oil refineries. Sulfur shares the chalcogen group with oxygen, selenium, and tellurium, and it is expected that organosulfur compounds have similarities with carbon–oxygen, carbon–selenium, and car ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfinate
Sulfinic acids are oxoacids of sulfur with the structure RSO(OH). In these organosulfur compounds, sulfur is Molecular geometry, pyramidal. Structure and properties Sulfinic acids RSO2H are typically more acidic than the corresponding carboxylic acid RCO2H. Sulfur is pyramidal, consequently sulfinic acids are chiral. The free acids are typically unstable, disproportionating to the sulfonic acid RSO3H and thiosulfonate RSSO2R. The formal anhydride of a sulfinic acid has no oxygen atom bridge, but is instead a sulfinyl sulfone (R–S+(–O−)–S2+(–O−)2–), and disproportionation is believed to occur through the free-radical fission of this intermediate. Alkylation of sulfinic acids can give either sulfones or sulfinate esters, depending on the solvent and reagent. Strongly polarized reactants (e.g. trimethyloxonium tetrafluoroborate) give esters, whereas relatively unpolarized reactants (e.g. an alkyl halide or enone) give sulfones. Sulf ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfolane
Sulfolane (also tetramethylene sulfone, IUPAC nomenclature, systematic name: 1λ6-thiolane-1,1-dione) is an organosulfur compound, formally a cyclic sulfone, with the formula . It is a colorless liquid commonly used in the chemical industry as a solvent for extractive distillation and chemical reactions. Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene. Sulfolane is a polar aprotic solvent, and it is miscible with water. Properties Sulfolane is classified as a sulfone, a group of organosulfur compounds containing a sulfonyl functional group. The sulfone group is a sulfur atom doubly bonded to two oxygen atoms and singly bonded to two carbon centers. The sulfur-oxygen double bond is polar, conferring good solubility in water, while the four carbon ring provides non-polar stability. These properties allow it to be miscible in both water and hydrocarbons, resulting in its widespread use as a solvent for purifying hydrocarbon mix ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfolane Synthesis
Sulfolane (also tetramethylene sulfone, systematic name: 1λ6-thiolane-1,1-dione) is an organosulfur compound, formally a cyclic sulfone, with the formula . It is a colorless liquid commonly used in the chemical industry as a solvent for extractive distillation and chemical reactions. Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene. Sulfolane is a polar aprotic solvent, and it is miscible with water. Properties Sulfolane is classified as a sulfone, a group of organosulfur compounds containing a sulfonyl functional group. The sulfone group is a sulfur atom doubly bonded to two oxygen atoms and singly bonded to two carbon centers. The sulfur-oxygen double bond is polar, conferring good solubility in water, while the four carbon ring provides non-polar stability. These properties allow it to be miscible in both water and hydrocarbons, resulting in its widespread use as a solvent for purifying hydrocarbon mixtures. Synthesis Th ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dimethyl Sulfoxide
Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula . This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO is metabolised to compounds that leave a garlic-like taste in the mouth after DMSO is absorbed by skin. In terms of chemical structure, the molecule has idealized Cs symmetry. It has a trigonal pyramidal molecular geometry consistent with other three-coordinate S(IV) compounds, with a nonbonded electron pair on the approximately tetrahedral sulfur atom. Synthesis and production Dimethyl sulfoxide was first synthesized in 1866 by the Russian scientist Alexander Zaytsev, who reported his findings in 1867. Its modern use as an industrial solvent began through popularization by Thor Smedslund at the Stepan Chemical Company. Dimeth ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Functional Group
In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The Reactivity (chemistry), reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive Chemical property, chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their Chemical polarity, nonp ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfonyl Halides
In chemistry, a sulfonyl halide consists of a sulfonyl () functional group, group Single bond, singly bonded to a halogen atom. They have the general Chemical formula, formula , where X is a halogen. The Chemical stability, stability of sulfonyl halides decreases in the order fluorides > chlorides > bromides > iodides, all four types being well known. The sulfonyl chlorides and fluorides are of dominant importance in this series. Sulfonyl halides have tetrahedral sulfur centres attached to two oxygen atoms, an organic radical, and a halide. In a representative example, methanesulfonyl chloride, the S=O, S−C, and S−Cl bond distances are respectively 142.4, 176.3, and 204.6 pm. Sulfonyl chlorides Sulfonic acid chlorides, or sulfonyl chlorides, are a sulfonyl halide with the general formula . Production Arylsulfonyl chlorides are made industrially in a two-step, one-pot reaction from an arene (in this case, benzene) and chlorosulfuric acid: : : The intermediate benzenes ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Dimethyl Sulfide
Dimethyl sulfide (DMS) or methylthiomethane is an organosulfur compound with the formula . It is the simplest thioether and has a characteristic disagreeable odor. It is a flammable liquid that boils at . It is a component of the smell produced from cooking of certain vegetables (notably maize, cabbage, and beetroot) and seafoods. It is also an indication of bacterial contamination in malt production and brewing. It is a breakdown product of dimethylsulfoniopropionate (DMSP), and is also produced by the bacterial metabolism of methanethiol. Occurrence and production DMS originates primarily from DMSP, a major secondary metabolite in some marine algae. DMS is the most abundant biological sulfur compound emitted to the atmosphere. Emission occurs over the oceans by phytoplankton. DMS is also produced naturally by bacterial transformation of dimethyl sulfoxide (DMSO) waste that is disposed of into sewers, where it can cause environmental odor problems. DMS is oxidized in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfonyl
In organosulfur chemistry, a sulfonyl group is either a functional group found primarily in sulfones, or a substituent obtained from a sulfonic acid by the removal of the hydroxyl group, similarly to acyl groups. Group Sulfonyl groups can be written as having the general formula , where there are two double bonds between the sulfur and oxygen. Sulfonyl groups can be reduced to the sulfide with diisobutylaluminium hydride (DIBALH). Lithium aluminium hydride () reduces some but not all sulfones to sulfides. In inorganic chemistry, when the group is not connected to any carbon atoms, it is referred to as sulfuryl. Examples of sulfonyl group substituents The names of sulfonyl groups typically end in -syl, such as: : See also * Sulfonyl halide * Sulfonamide * Sulfonate * Methylsulfonylmethane Dimethyl sulfone (DMSO2) is an organosulfur compound with the formula . It is also known by several other names including methyl sulfone and (especially in alternative medicine) methyl ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Sulfoxide
In organic chemistry, a sulfoxide, also called a sulphoxide, is an organosulfur compound containing a sulfinyl () functional group attached to two carbon atoms. It is a polar functional group. Sulfoxides are oxidized derivatives of sulfides. Examples of important sulfoxides are alliin, a precursor to the compound that gives freshly crushed garlic its aroma, and dimethyl sulfoxide (DMSO), a common solvent. Structure and bonding Sulfoxides feature relatively short S–O distances. In DMSO, the S–O distance is 1.531 Å. The sulfur center is pyramidal; the sum of the angles at sulfur is about 306°.. Sulfoxides are generally represented with the structural formula R−S(=O)−R', where R and R' are organic groups. The bond between the sulfur and oxygen atoms is intermediate of a dative bond and a polarized double bond. The double-bond resonance form implies 10 electrons around sulfur (10-S-3 in N-X-L notation). The double-bond character of the S−O bond may be accou ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
