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Trimethylsulfoxonium

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Trimethylsulfoxonium
Names
IUPAC name Trimethyl(oxo)-λ-sulfanium
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H9OS/c1-5(2,3)4/h1-3H3/q+1Key: YRYSAWZMIRQUBO-UHFFFAOYSA-N
SMILES
  • C(=O)(C)C
Properties
Chemical formula C3H9OS
Molar mass 93.16 g·mol
Related compounds
Related compounds trimethylsulfonium; trimethylselenoxonium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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.

Production

Refluxing dimethyl sulfoxide with methyl iodide can yield trimethylsulfoxonium iodide.

Reactions

Treated with sodium hydride, trimethylsulfoxonium forms dimethylsulfoxonium methylide.

Trimethylsulfoxonium can polymerise to yield polyethylene.

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

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°.

List of compounds

name formula crystal Å volume density comment reference
trimethylsulfoxonium phthalimide orthorhombic Pnma a=8.445 b=10.958 c=12.084 Z=4 1118.2 colourless
Trimethylsulfoxonium nitrate
Trimethylsulfoxonium tetraphenylborate Ph4B P21/m a=9.482 b=12.790 c=9.713 β=106.48° Z=2 1130 1.177
Trimethylsulfoxonium chloride Cl white; sublime 227°C
Trimethylsulfoxonium chromate
trimethylsulfoxonium tetrachloridocobaltate(II) 2CoCl4 monoclinic, P21/c a = 8.4397, b = 15.6692, c = 12.5989, β = 93.858°, Z = 4 1662.3 blue
Trimethylsulfoxonium bromide
Trimethylsulfoxonium iodide I yellow; dec 170°C
Cu2I3 Pnma
Ag2I3 Pnma
trimethyloxosulfonium trichloro-cadmate CdCl3 orthorhombic Pnma a=6.688 b=10.147 c=13.446 Z=4 912.5 2.270
trimethyloxosulfonium tribromo-cadmate CdBr3 orthorhombic Pnma a=6.946 b=10.543 c=13.782 Z=4 1009.3 2.928 colourless
bis(trimethylsulfoxonium) catena-poly 2NaInBr6 orthorhombic, Pmn21, a = 10.5451, b = 7.1169, c = 13.7034, Z = 2 1028.42 colourless
PbBr3 orthorhombic Pnma a=7.5697 b=10.7768 c=13.9143 Z=4 1135.09 3.160 white
PbI3 orthorhombic Pnma a=7.8157 b=11.1996 c=14.3780 Z=4 1260.29 3.590 light yellow; band gap 2.30 eV
3Bi2Br9 orthorhombic Pnma a=7.0351 b=10.6613 c=13.9190 1043.98 3.004 light yellow
3Bi2I9 orthorhombic Pnma a=7.4530 b=11.2169 c=14.4009 1203.92 3.383 red

References

  1. ^ Ng, John S.; Liu, Chin; McGarrigle, Eoghan M.; Aggarwal, Varinder K. (2007-03-15), "Trimethylsulfoxonium Iodide", in John Wiley & Sons, Ltd. (ed.), Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/9780470842898.rt351.pub2, ISBN 978-0-471-93623-7, retrieved 2024-01-22
  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. ^ 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. ^ 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. ^ 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 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. ^ 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. hdl:10447/519176. 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.
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