Trimethylsulfoxonium

Last updated
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]

References

  1. 1 2 3 4 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. 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. 63 (4): 2174–2184. doi:10.1021/acs.inorgchem.3c04119. PMID   38235735.
  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. 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. Bibcode:2021MTEne..2100803R. doi: 10.1016/j.mtener.2021.100803 .
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.