Trimethylsulfoxonium

Trimethylsulfoxonium
Names
	IUPAC name Trimethyl(oxo)-λ4-sulfanium
Identifiers
CAS Number	47987-92-8;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1183173;
ChemSpider	67080;
PubChem CID	74499;
	InChI InChI=1S/C3H9OS/c1-5(2,3)4/h1-3H3/q+1 Key: YRYSAWZMIRQUBO-UHFFFAOYSA-N;
	SMILES C[S+](=O)(C)C;
Properties
Chemical formula	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).
	Infobox references

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.^[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

name	formula	crystal Å	volume	density	comment	reference
trimethylsulfoxonium phthalimide	[C₃H₉SO][C₈H₄NO₂]	orthorhombic Pnma a=8.445 b=10.958 c=12.084 Z=4	1118.2		colourless	^[6]
Trimethylsulfoxonium nitrate						^[7]
Trimethylsulfoxonium tetraphenylborate	[(CH₃)₃SO]Ph₄B	P2₁/m a=9.482 b=12.790 c=9.713 β=106.48° Z=2	1130	1.177		^[5]
Trimethylsulfoxonium chloride	[(CH₃)₃SO]Cl				white; sublime 227°C	^[7]^[1]
Trimethylsulfoxonium chromate						^[7]
trimethylsulfoxonium tetrachloridocobaltate(II)	[(CH₃)₃SO]₂CoCl₄	monoclinic, P2₁/c a = 8.4397, b = 15.6692, c = 12.5989, β = 93.858°, Z = 4	1662.3		blue	^[8]
Trimethylsulfoxonium bromide						^[7]
Trimethylsulfoxonium iodide	[(CH₃)₃SO]I				yellow; dec 170°C	^[7]^[1]
	[(CH₃)₃SO]Cu₂I₃	Pnma				^[9]
	[(CH₃)₃SO]Ag₂I₃	Pnma				^[9]
trimethyloxosulfonium trichloro-cadmate	[(CH₃)₃SO]CdCl₃	orthorhombic Pnma a=6.688 b=10.147 c=13.446 Z=4	912.5	2.270		^[7]
trimethyloxosulfonium tribromo-cadmate	[(CH₃)₃SO]CdBr₃	orthorhombic Pnma a=6.946 b=10.543 c=13.782 Z=4	1009.3	2.928	colourless	^[7]
bis(trimethylsulfoxonium) catena-poly[µ₂-hexabromido-indium(III)sodium(I)]	[(CH₃)₃SO]₂NaInBr₆	orthorhombic, Pmn2₁, a = 10.5451, b = 7.1169, c = 13.7034, Z = 2	1028.42		colourless	^[10]
	[(CH₃)₃SO]PbBr₃	orthorhombic Pnma a=7.5697 b=10.7768 c=13.9143 Z=4	1135.09	3.160	white	^[11]
	[(CH₃)₃SO]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	^[12]
	[(CH₃)₃SO]₃Bi₂Br₉	orthorhombic Pnma a=7.0351 b=10.6613 c=13.9190	1043.98	3.004	light yellow	^[11]
	[(CH₃)₃SO]₃Bi₂I₉	orthorhombic Pnma a=7.4530 b=11.2169 c=14.4009	1203.92	3.383	red	^[11]

References

↑ ^1.0 ^1.1 ^1.2 ^1.3 Ng, John S.; Liu, Chin; McGarrigle, Eoghan M.; Aggarwal, Varinder K. (2007-03-15), John Wiley & Sons, Ltd., ed. (in en), Trimethylsulfoxonium Iodide, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/9780470842898.rt351.pub2, ISBN 978-0-471-93623-7, https://onlinelibrary.wiley.com/doi/10.1002/9780470842898.rt351.pub2, retrieved 2024-01-22
↑ "Polyethylene from Trimethylsulfoxonium Halide in Water". Synfacts 8 (08): 0845. August 2012. doi:10.1055/s-0032-1316727.
↑ 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.
↑ 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.
↑ ^5.0 ^5.1 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" (in en). Canadian Journal of Chemistry 72 (8): 1870–1881. doi:10.1139/v94-238. ISSN 0008-4042. http://www.nrcresearchpress.com/doi/10.1139/v94-238.
↑ 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. https://www.degruyter.com/document/doi/10.1524/ncrs.2011.0155/html.
↑ ^7.0 ^7.1 ^7.2 ^7.3 ^7.4 ^7.5 ^7.6 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. doi:10.1107/S0108270190013701. Bibcode: 1991AcCrC..47.1803P. https://scripts.iucr.org/cgi-bin/paper?S0108270190013701.
↑ Zhong, Xin; Zhou, Junyan; Hao, Munan (2020-06-25). "Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH 3 ) 3 SO 2 CoCl 4"] (in en). Zeitschrift für Kristallographie - New Crystal Structures 235 (4): 1001–1002. doi:10.1515/ncrs-2020-0159. ISSN 2197-4578. https://www.degruyter.com/document/doi/10.1515/ncrs-2020-0159/html.
↑ ^9.0 ^9.1 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.
↑ 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"] (in en). Zeitschrift für Kristallographie - New Crystal Structures 238 (6): 1171–1173. doi:10.1515/ncrs-2023-0377. ISSN 1433-7266. https://www.degruyter.com/document/doi/10.1515/ncrs-2023-0377/html.
↑ ^11.0 ^11.1 ^11.2 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)" (in en). The Journal of Physical Chemistry C 125 (21): 11728–11742. doi:10.1021/acs.jpcc.1c02571. ISSN 1932-7447. https://pubs.acs.org/doi/10.1021/acs.jpcc.1c02571.
↑ 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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Original source: https://en.wikipedia.org/wiki/Trimethylsulfoxonium. Read more

[:2-1] 1.0 ^1.1 ^1.2 ^1.3 Ng, John S.; Liu, Chin; McGarrigle, Eoghan M.; Aggarwal, Varinder K. (2007-03-15), John Wiley & Sons, Ltd., ed. (in en), Trimethylsulfoxonium Iodide, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/9780470842898.rt351.pub2, ISBN 978-0-471-93623-7, https://onlinelibrary.wiley.com/doi/10.1002/9780470842898.rt351.pub2, retrieved 2024-01-22

[2] "Polyethylene from Trimethylsulfoxonium Halide in Water". Synfacts 8 (08): 0845. August 2012. doi:10.1055/s-0032-1316727.

[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.

[:3-5] 5.0 ^5.1 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" (in en). Canadian Journal of Chemistry 72 (8): 1870–1881. doi:10.1139/v94-238. ISSN 0008-4042. http://www.nrcresearchpress.com/doi/10.1139/v94-238.

[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. https://www.degruyter.com/document/doi/10.1524/ncrs.2011.0155/html.

[:0-7] 7.0 ^7.1 ^7.2 ^7.3 ^7.4 ^7.5 ^7.6 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. doi:10.1107/S0108270190013701. Bibcode: 1991AcCrC..47.1803P. https://scripts.iucr.org/cgi-bin/paper?S0108270190013701.

[8] Zhong, Xin; Zhou, Junyan; Hao, Munan (2020-06-25). "Crystal structure of trimethylsulfoxonium tetrachloridocobaltate(II) [(CH 3 ) 3 SO 2 CoCl 4"] (in en). Zeitschrift für Kristallographie - New Crystal Structures 235 (4): 1001–1002. doi:10.1515/ncrs-2020-0159. ISSN 2197-4578. https://www.degruyter.com/document/doi/10.1515/ncrs-2020-0159/html.

[pinky-9] 9.0 ^9.1 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"] (in en). Zeitschrift für Kristallographie - New Crystal Structures 238 (6): 1171–1173. doi:10.1515/ncrs-2023-0377. ISSN 1433-7266. https://www.degruyter.com/document/doi/10.1515/ncrs-2023-0377/html.

[:1-11] 11.0 ^11.1 ^11.2 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)" (in en). The Journal of Physical Chemistry C 125 (21): 11728–11742. doi:10.1021/acs.jpcc.1c02571. ISSN 1932-7447. https://pubs.acs.org/doi/10.1021/acs.jpcc.1c02571.

[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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