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| Names | |
|---|---|
| IUPAC name Trimethylsulfonium | |
| Systematic IUPAC name Trimethylsulfanium | |
Other names
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| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
PubChem CID | |
| UNII | |
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| Properties | |
| (CH3)3S+ | |
| Molar mass | 77.17 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Trimethylsulfonium (systematically named trimethylsulfanium) is an organic cation with the chemical formula (C H 3)3 S + (also written as C3H9S+).
Several salts of trimethylsulfonium are known. X-ray crystallography reveals that the ion has trigonal pyramidal molecular geometry at sulfur atom, with C-S-C angles near 102° and C-S bond distance of 177 picometers. Unless the counteranion is colored, all trimethylsulfonium salts are white or colorless.
| Salt | Formula | Molecular weight (g/mol) | Properties [2] |
|---|---|---|---|
| Trimethylsulfonium chloride | [(CH3)3S]+Cl− | 112.5 | Colorless crystals, decompose at 100 °C, very soluble in ethanol, very hygroscopic. [3] |
| Trimethylsulfonium bromide | [(CH3)3S]+Br− | 157 | Colorless crystals. Decomposes at 172 °C, melts in a sealed tube at 201-201 °C, reacts in neutral aqueous solution.[ clarification needed ] [4] |
| Trimethylsulfonium iodide | [(CH3)3S]+I− | 204 | Colorless crystals, decomposes at 203-207 °C. [4] [5] crystal structure monoclinic, with these parameters: a = 5.94 μm, b = 8.00 μm, c = 8.92 μm, β = 126°32′ 2 formulas per unit cell,[ clarification needed ] density = 1.958 g/cm3 [6] |
| Trimethylsulfonium tetrafluoroborate | [(CH3)3S]+[BF4]− | 163.97 | melting point = 205-210 °C [7] |
| Trimethylsulfonium methylsulfate | [(CH3)3S]+CH3OSO−3 | 188.27 | melting point = 92-94 °C [8] Crystal structure orthorhombic with these parameters: a = 12.6157 μm, b = 8.2419 μm, c = 7.540 μm cell volume 784.0 2 formulas per unit cell[ clarification needed ] |
Sulfonium compounds can be synthesised by treating a suitable alkyl halide with a thioether. For example, the reaction of dimethyl sulfide with iodomethane yields trimethylsulfonium iodide:
An extra oxygen atom can bond to the sulfur atom to yield the trimethylsulfoxonium ion [(CH3)3S=O]+, where the sulfur atom is tetravalent and tetracoordinated.
Glyphosate herbicide is often supplied as a trimethylsulfonium salt, referred to as trimesium. [9]
When mixed with aluminium bromide, or aluminium chloride or even hydrogen bromide, trimethylsulfonium bromide forms an ionic liquid, which melts at temperatures below standard conditions. [10]
The halogens are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and the radioactive elements astatine (At) and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group 17.
The haloalkanes are alkanes containing one or more halogen substituents. They are a subset of the general class of halocarbons, although the distinction is not often made. Haloalkanes are widely used commercially. They are used as flame retardants, fire extinguishants, refrigerants, propellants, solvents, and pharmaceuticals. Subsequent to the widespread use in commerce, many halocarbons have also been shown to be serious pollutants and toxins. For example, the chlorofluorocarbons have been shown to lead to ozone depletion. Methyl bromide is a controversial fumigant. Only haloalkanes that contain chlorine, bromine, and iodine are a threat to the ozone layer, but fluorinated volatile haloalkanes in theory may have activity as greenhouse gases. Methyl iodide, a naturally occurring substance, however, does not have ozone-depleting properties and the United States Environmental Protection Agency has designated the compound a non-ozone layer depleter. For more information, see Halomethane. Haloalkane or alkyl halides are the compounds which have the general formula "RX" where R is an alkyl or substituted alkyl group and X is a halogen.
Sodium iodide (chemical formula NaI) is an ionic compound formed from the chemical reaction of sodium metal and iodine. Under standard conditions, it is a white, water-soluble solid comprising a 1:1 mix of sodium cations (Na+) and iodide anions (I−) in a crystal lattice. It is used mainly as a nutritional supplement and in organic chemistry. It is produced industrially as the salt formed when acidic iodides react with sodium hydroxide. It is a chaotropic salt.
![<span class="mw-page-title-main">Sulfonium</span> Cation of the form [SR3]+](https://upload.wikimedia.org/wikipedia/commons/thumb/6/62/%28CH3%293S%2B_in_the_BPh4-_salt_%28code_HEYZAM%29.png/320px-%28CH3%293S%2B_in_the_BPh4-_salt_%28code_HEYZAM%29.png)
In organic chemistry, a sulfonium ion, also known as sulphonium ion or sulfanium ion, is a positively-charged ion featuring three organic substituents attached to sulfur. These organosulfur compounds have the formula [SR3]+. Together with a negatively-charged counterion, they give sulfonium salts. They are typically colorless solids that are soluble in organic solvent.
Palladium(II) acetate is a chemical compound of palladium described by the formula [Pd(O2CCH3)2]n, abbreviated [Pd(OAc)2]n. It is more reactive than the analogous platinum compound. Depending on the value of n, the compound is soluble in many organic solvents and is commonly used as a catalyst for organic reactions.
The tropylium ion or cycloheptatrienyl cation is an aromatic species with a formula of [C7H7]+. Its name derives from the molecule tropine from which cycloheptatriene (tropylidene) was first synthesized in 1881. Salts of the tropylium cation can be stable, even with nucleophiles of moderate strength e.g., tropylium tetrafluoroborate and tropylium bromide (see below). Its bromide and chloride salts can be made from cycloheptatriene and bromine or phosphorus pentachloride, respectively.
A halonium ion is any onium ion containing a halogen atom carrying a positive charge. This cation has the general structure R−−R′ where X is any halogen and no restrictions on R, this structure can be cyclic or an open chain molecular structure. Halonium ions formed from fluorine, chlorine, bromine, and iodine are called fluoronium, chloronium, bromonium, and iodonium, respectively. The 3-membered cyclic variety commonly proposed as intermediates in electrophilic halogenation may be called haliranium ions, using the Hantzsch-Widman nomenclature system.
Copper(I) bromide is the chemical compound with the formula CuBr. This diamagnetic solid adopts a polymeric structure akin to that for zinc sulfide. The compound is widely used in the synthesis of organic compounds and as a lasing medium in copper bromide lasers.
In organic chemistry, a dithiocarbamate is a functional group with the general formula R2N−C(=S)−S−R and structure >N−C(=S)−S−. It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms.
The thallium halides include monohalides, where thallium has oxidation state +1, trihalides in which thallium generally has oxidation state +3, and some intermediate halides containing thallium with mixed +1 and +3 oxidation states. These salts find use in specialized optical settings, such as focusing elements in research spectrophotometers. Compared to the more common zinc selenide-based optics, materials such as thallium bromoiodide enable transmission at longer wavelengths. In the infrared, this allows for measurements as low as 350 cm−1 (28 μm), whereas zinc selenide is opaque by 21.5 μm, and ZnSe optics are generally only usable to 650 cm−1 (15 μm).
There are three sets of Indium halides, the trihalides, the monohalides, and several intermediate halides. In the monohalides the oxidation state of indium is +1 and their proper names are indium(I) fluoride, indium(I) chloride, indium(I) bromide and indium(I) iodide.
Sodium tetraphenylborate is the organic compound with the formula NaB(C6H5)4. It is a salt, wherein the anion consists of four phenyl rings bonded to boron. This white crystalline solid is used to prepare other tetraphenylborate salts, which are often highly soluble in organic solvents. The compound is used in inorganic and organometallic chemistry as a precipitating agent for potassium, ammonium, rubidium, and cesium ions, and some organic nitrogen compounds.
Tin(IV) bromide is the chemical compound SnBr4. It is a colourless low melting solid.
An aryl radical in organic chemistry is a reactive intermediate and an arene compound incorporating one free radical carbon atom as part of the ring structure. As such it is the radical counterpart of the arenium ion. The parent compound is the phenyl radical C
6H•
5. Aryl radicals are intermediates in certain organic reactions.
Zinc compounds are chemical compounds containing the element zinc which is a member of the group 12 of the periodic table. The oxidation state of zinc in most compounds is the group oxidation state of +2. Zinc may be classified as a post-transition main group element with zinc(II). Zinc compounds are noteworthy for their nondescript appearance and behavior: they are generally colorless, do not readily engage in redox reactions, and generally adopt symmetrical structures.
Difluorophosphate or difluorodioxophosphate or phosphorodifluoridate is an anion with formula PO2F−2. It has a single negative charge and resembles perchlorate and monofluorosulfonate in shape and compounds. These ions are isoelectronic, along with tetrafluoroaluminate, phosphate, orthosilicate, and sulfate. It forms a series of compounds. The ion is toxic to mammals as it causes blockage to iodine uptake in the thyroid. However it is degraded in the body over several hours.
Nickel compounds are chemical compounds containing the element nickel which is a member of the group 10 of the periodic table. Most compounds in the group have an oxidation state of +2. Nickel is classified as a transition metal with nickel(II) having much chemical behaviour in common with iron(II) and cobalt(II). Many salts of nickel(II) are isomorphous with salts of magnesium due to the ionic radii of the cations being almost the same. Nickel forms many coordination complexes. Nickel tetracarbonyl was the first pure metal carbonyl produced, and is unusual in its volatility. Metalloproteins containing nickel are found in biological systems.
Zirconium(III) iodide is an inorganic compound with the formula ZrI3.
Protactinium compounds are compounds containing the element protactinium. These compounds usually have protactinium in the +5 oxidation state, although these compounds can also exist in the +2, +3 and +4 oxidation states.
Trimethylsulfoxonium (abbreviated TMSO) is a cation with a formula (CH3)3SO+ consisting of a sulfur atom attached to three methyl groups and one oxygen atom. It has a net charge of +1.
