Trimethylsulfoxonium

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Trimethylsulfoxonium
Trimethylsulfoxonium.png
Names
IUPAC name
Trimethyl(oxo)-λ4-sulfanium
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C3H9OS/c1-5(2,3)4/h1-3H3/q+1
    Key: YRYSAWZMIRQUBO-UHFFFAOYSA-N
  • C[S+](=O)(C)C
Properties
C3H9OS+
Molar mass 93.16 g·mol−1
Related compounds
Related compounds
trimethylsulfonium; trimethylselenoxonium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Contents

Production

Refluxing dimethyl sulfoxide with methyl iodide can yield trimethylsulfoxonium iodide. [1]

Reactions

Treated with sodium hydride, trimethylsulfoxonium forms dimethylsulfoxonium methylide. [1]

Trimethylsulfoxonium can polymerise to yield polyethylene. [2] [3]

Copper, zinc and palladium ions in water react with trimethylsulfoxonium and sodium hydroxide to form sulfur ylide complexes. [4]

Properties

In the chloride, the sulfur-oxygen bond length is 1.436 Å, sulfur-carbon bond is 1.742. OSC angles are 112.6°, and CSC angles are 106.2°. [5]

List of compounds

nameformulacrystal Åvolumedensitycommentreference
trimethylsulfoxonium phthalimide[C3H9SO][C8H4NO2]orthorhombic Pnma a=8.445 b=10.958 c=12.084 Z=41118.2colourless [6]
Trimethylsulfoxonium nitrate [7]
Trimethylsulfoxonium tetraphenylborate[(CH3)3SO]Ph4BP21/m a=9.482 b=12.790 c=9.713 β=106.48° Z=211301.177 [5]
Trimethylsulfoxonium chloride[(CH3)3SO]Clwhite; sublime 227°C [7] [1]
Trimethylsulfoxonium chromate [7]
trimethylsulfoxonium tetrachloridocobaltate(II)[(CH3)3SO]2CoCl4monoclinic, P21/ca = 8.4397, b = 15.6692, c = 12.5989, β = 93.858°, Z = 41662.3blue [8]
Trimethylsulfoxonium bromide [7]
Trimethylsulfoxonium iodide [(CH3)3SO]Iyellow; dec 170°C [7] [1]
[(CH3)3SO]Cu2I3Pnma [9]
[(CH3)3SO]Ag2I3Pnma [9]
trimethyloxosulfonium trichloro-cadmate[(CH3)3SO]CdCl3orthorhombic Pnma a=6.688 b=10.147 c=13.446 Z=4912.52.270 [7]
trimethyloxosulfonium tribromo-cadmate[(CH3)3SO]CdBr3orthorhombic Pnma a=6.946 b=10.543 c=13.782 Z=41009.32.928colourless [7]
bis(trimethylsulfoxonium) catena-poly[µ2-hexabromido-indium(III)sodium(I)][(CH3)3SO]2NaInBr6orthorhombic, Pmn21, a = 10.5451, b = 7.1169, c = 13.7034, Z = 21028.42colourless [10]
[(CH3)3SO]PbBr3orthorhombic Pnma a=7.5697 b=10.7768 c=13.9143 Z=41135.093.160white [11]
[(CH3)3SO]PbI3orthorhombic Pnma a=7.8157 b=11.1996 c=14.3780 Z=41260.293.590light yellow; band gap 2.30 eV [12]
[(CH3)3SO]3Bi2Br9orthorhombic Pnma a=7.0351 b=10.6613 c=13.91901043.983.004light yellow [11]
[(CH3)3SO]3Bi2I9orthorhombic Pnma a=7.4530 b=11.2169 c=14.40091203.923.383red [11]

Related Research Articles

<span class="mw-page-title-main">Sulfonium</span> Cation of the form [SR3]+

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.

<span class="mw-page-title-main">Copper(I) iodide</span> Chemical compound

Copper(I) iodide is the inorganic compound with the formula CuI. It is also known as cuprous iodide. It is useful in a variety of applications ranging from organic synthesis to cloud seeding.

The polyiodides are a class of polyhalogen anions composed entirely of iodine atoms. The most common member is the triiodide ion, I
3
. Other known larger polyiodides include [I4]2−, [I5], [I6]2−, [I7], [I8]2−, [I9], [I10]2−, [I10]4−, [I11]3−, [I12]2−, [I13]3−, [I14]4-, [I16]2−, [I22]4−, [I26]3−, [I26]4−, [I28]4− and [I29]3−. All these can be considered as formed from the interaction of the I, I2, and I
3
building blocks.

<span class="mw-page-title-main">Trimethylsulfonium</span> Ion

Trimethylsulfonium is an organic cation with the chemical formula (CH3)3S+.

<span class="mw-page-title-main">Methylammonium lead halide</span>

Methylammonium lead halides (MALHs) are solid compounds with perovskite structure and a chemical formula of [CH3NH3]+Pb2+(X)3, where X = Cl, Br or I. They have potential applications in solar cells, lasers, light-emitting diodes, photodetectors, radiation detectors, scintillator, magneto-optical data storage and hydrogen production.

The borate fluorides or fluoroborates are compounds containing borate or complex borate ions along with fluoride ions that form salts with cations such as metals. They are in the broader category of mixed anion compounds. They are not to be confused with tetrafluoroborates (BF4) or the fluorooxoborates which have fluorine bonded to boron.

The selenide iodides are chemical compounds that contain both selenide ions (Se2−) and iodide ions (I) and one or metal atoms. They are in the class of mixed anion compounds or chalcogenide halides.

The telluride iodides are chemical compounds that contain both telluride ions (Te2−) and iodide ions (I). They are in the class of mixed anion compounds or chalcogenide halides.

The borophosphates are mixed anion compounds containing borate and phosphate anions, which may be joined together by a common oxygen atom. Compounds that contain water or hydroxy groups can also be included in the class of compounds.

A chloride nitride is a mixed anion compound containing both chloride (Cl) and nitride ions (N3−). Another name is metallochloronitrides. They are a subclass of halide nitrides or pnictide halides.

<span class="mw-page-title-main">Germanium tetrabromide</span> Chemical compound

Germanium tetrabromide is the inorganic compound with the formula GeBr4. It is a colorless solid that melts near room temperature. It can be formed by treating solid germanium with bromine, or by treating a germanium-copper mixture with bromine:

Phosphide iodides or iodide phosphides are compounds containing anions composed of iodide (I) and phosphide (P3−). They can be considered as mixed anion compounds. They are in the category of pnictidehalides. Related compounds include the phosphide chlorides, arsenide iodides antimonide iodides and phosphide bromides.

Phosphide bromides or bromide phosphides are compounds containing anions composed of bromide (Br) and phosphide (P3−) anions. Usually phosphorus is covalently connected into more complex structures. They can be considered as mixed anion compounds. They are in the category of pnictidehalides. Related compounds include the phosphide chlorides, phosphide iodides, nitride bromides, arsenide bromides, and antimonide bromides.

Arsenide bromides or bromide arsenides are compounds containing anions composed of bromide (Br) and arsenide (As3−). They can be considered as mixed anion compounds. They are in the category of pnictidehalides. Related compounds include the arsenide chlorides, arsenide iodides, phosphide bromides, and antimonide bromides.

Arsenide iodides or iodide arsenides are compounds containing anions composed of iodide (I) and arsenide (As3−). They can be considered as mixed anion compounds. They are in the category of pnictidehalides. Related compounds include the arsenide chlorides, arsenide bromides, phosphide iodides, and antimonide iodides.

An iodide nitride is a mixed anion compound containing both iodide (I) and nitride ions (N3−). Another name is metalloiodonitrides. They are a subclass of halide nitrides or pnictide halides. Some different kinds include ionic alkali or alkaline earth salts, small clusters where metal atoms surround a nitrogen atom, layered group 4 element 2-dimensional structures, and transition metal nitrido complexes counter-balanced with iodide ions. There is also a family with rare earth elements and nitrogen and sulfur in a cluster.

Carbide iodides are mixed anion compounds containing iodide and carbide anions. Many carbide iodides are cluster compounds, containing one, two or more carbon atoms in a core, surrounded by a layer of metal atoms, and encased in a shell of iodide ions. These ions may be shared between clusters to form chains, double chains or layers.

<span class="mw-page-title-main">Praseodymium orthoscandate</span> Chemical compound

Praseodymium orthoscandate is a chemical compound, a rare-earth oxide with a perovskite structure. It has the chemical formula of PrScO3.

<span class="mw-page-title-main">Europium(III) arsenate</span> Chemical compound

Europium(III) arsenate is an arsenate salt of europium, with the chemical formula of EuAsO4. It has good thermal stability, with its pKsp,c of 22.53±0.03. It is a colorless crystal with a xenotime structure.

Barium selenate is an inorganic compound with the chemical formula BaSeO4. It is isomorphous with barium sulfate, but its solubility is 18 times that of barium sulfate, and its thermal stability is worse than that of barium sulfate.

References

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  2. "Polyethylene from Trimethylsulfoxonium Halide in Water". Synfacts. 8 (08): 0845. August 2012. doi:10.1055/s-0032-1316727. S2CID   99933705.
  3. Luo, Jun; Lu, Fangfang; Shea, Kenneth J. (15 May 2012). "Hydrocarbon Waxes from a Salt in Water: The C1 Polymerization of Trimethylsulfoxonium Halide". ACS Macro Letters. 1 (5): 560–563. doi:10.1021/mz300140x. PMID   35607061.
  4. Lin, Ivan J.B.; Hwan, Luchen; Shy, Hwai C.; Chen, M.C.; Wang, Y. (November 1986). "The synthesis of sulfur ylide complexes of palladium, zinc and copper in water". Journal of Organometallic Chemistry. 315 (1): 135–142. doi:10.1016/0022-328X(86)80418-1.
  5. 1 2 Knop, Osvald; Cameron, T. Stanley; Bakshi, Pradip K.; Linden, Antony; Roe, Stephen P. (1994-08-01). "Crystal chemistry of tetraradial species. Part 5. Interaction between cation lone pairs and phenyl groups in tetraphenylborates: crystal structures of Me 3 S + ,Et 3 S + ,Me 3 SO + ,Ph 2 I + , and 1-azoniapropellane tetraphenylborates". Canadian Journal of Chemistry. 72 (8): 1870–1881. doi:10.1139/v94-238. ISSN   0008-4042.
  6. Mallah, Eyad; Abu-Salem, Qutaiba; Dayyih, Wael Abu; Hamad, Mohammed; Steimann, Manfred; Maichle-Mössmer, Caecilia (2011-01-01). "Crystal structure of trimethylsulfoxonium phthalimide, [C3H9SO][C8H4NO2]". Zeitschrift für Kristallographie - New Crystal Structures. 226 (3). doi:10.1524/ncrs.2011.0155. ISSN   2197-4578.
  7. 1 2 3 4 5 6 7 Puget, R.; Jannin, M.; de Brauer, C.; Perret, R. (1991-09-15). "Structures oftrimethyloxosulfonium salts. V. The catena-tri-μ-chloro-cadmate and the catena-tri-μ-bromo-cadmate". Acta Crystallographica Section C Crystal Structure Communications. 47 (9): 1803–1805. Bibcode:1991AcCrC..47.1803P. doi:10.1107/S0108270190013701.
  8. Zhong, Xin; Zhou, Junyan; Hao, Munan (2020-06-25). "Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH 3 ) 3 SO] 2 CoCl 4". Zeitschrift für Kristallographie - New Crystal Structures. 235 (4): 1001–1002. doi:10.1515/ncrs-2020-0159. ISSN   2197-4578.
  9. 1 2 Pinky, Tamanna; Popy, Dilruba A.; Zhang, Zheng; Jiang, Jie; Pachter, Ruth; Saparov, Bayram (18 January 2024). "Synthesis and Characterization of New Hybrid Organic–Inorganic Metal Halides [(CH 3 ) 3 SO]M 2 I 3 (M = Cu and Ag)". Inorganic Chemistry. doi:10.1021/acs.inorgchem.3c04119.
  10. Jin, Shifeng; Lu, Jiali (2023-12-15). "The crystal structure of bis(trimethylsulfoxonium) catena -poly[µ 2 -hexabromido-indium(III)sodium(I)] C 6 H 18 O 2 S 2 NaInBr 6". Zeitschrift für Kristallographie - New Crystal Structures. 238 (6): 1171–1173. doi:10.1515/ncrs-2023-0377. ISSN   1433-7266.
  11. 1 2 3 Pipitone, Candida; Giannici, Francesco; Martorana, Antonino; García-Espejo, Gonzalo; Carlotto, Silvia; Casarin, Maurizio; Guagliardi, Antonietta; Masciocchi, Norberto (2021-06-03). "Heterovalent Bi III /Pb II Ionic Substitution in One-Dimensional Trimethylsulfoxonium Halide Pseudo-Perovskites (X = I, Br)". The Journal of Physical Chemistry C. 125 (21): 11728–11742. doi:10.1021/acs.jpcc.1c02571. ISSN   1932-7447.
  12. Rahman, Md. Mahbubur; Ge, Chuang-ye; Yoo, Kicheon; Lee, Jae-Joon (September 2021). "Aqueous phase synthesis of trimethylsulfoxonium lead triiodide for moisture-stable perovskite solar cells". Materials Today Energy. 21: 100803. doi:10.1016/j.mtener.2021.100803.