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词条 Trimethylsulfonium
释义

  1. Compounds

  2. Preparation

  3. Related

  4. Use

  5. References

  6. See also

{{Chembox
| ImageFile = Trimethylsulfonium.svg
| ImageSize = 120px
| ImageAlt =
| IUPACName =
| OtherNames = Trimesium
| Section1 = {{Chembox Identifiers
| CASNo = 676-84-6
| PubChem =
| ChemSpiderID = 1115
| SMILES = C[S+](C)C
| Section2 = {{Chembox Properties
| Formula = C3H9S+
| MolarMass = 77.17 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

Trimethylsulfonium (systematically named trimethylsulfanium and trimethylsulfur(1+)) is an organic cation with the chemical formula (CH3)3S+ (also written as {{Chem|C|3|H|9|S|+}}). It is the simplest sulfonium cation.

Compounds

Several salts of trimethylsulfonium are known:

Salt Molecular formula Chemical formula Molecular weight (g/mol) Properties[1]
Trimethylsulfonium chloride (CH3)3SCl C3H9ClS 112.5 Colorless crystals, decompose at 100 °C, very soluble in ethanol, very hygroscopic.[2]
Trimethylsulfonium bromide (CH3)3SBr C3H9BrS 157 Colorless crystals from H2O. Decomposes at 172 °C, melts in a sealed tube at 201-201 °C, reacts in neutral aqueous solution.[3]
Trimethylsulfonium iodide (CH3)3SI C3H9IS 204 Colorless crystals from ethanol, decomposes at 203-207 °C.[3][4] crystal structure monoclinic a=5.94 b=8.00 c=8.92 μm β=126°32′ 2 formulas per unit cell density=1.958[5]
Trimethylsulfonium tetrafluoroborate (CH3)3SBF4 C3H9BF4S 163.97 mp 205-210°[6]
Trimethylsulfonium methylsulfate (CH3)3SSO4CH2 C4H12O4S2 188.27 mp 92-94°[7] Crystal structure orthorhombic a=12.6157 b=8.2419 μm c=7.540 cell volume 784.0 2 formulas per unit cell

Preparation

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:

CH3–S–CH3 + CH3–I → (CH3)3SI

Related

An extra oxygen atom can bond to the sulfur atom to yield the trimethylsulfoxonium ion.

Use

Glyphosate herbicide is often supplied as a trimethylsulfonium salt.

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.[8]

References

1. ^Heilbron's Dictionary of Organic Compounds, volume 4, revised edition published in 1953. Published in Great Britain
2. ^{{cite journal|year = 1919|volume = 40|issue = 8|pages = 417–429|title = Über Trimethylsulfoniumverbindungen|journal = Monatshefte für Chemie und verwandte Teile anderer Wissenschaften|first = H.|last = Blättler|doi = 10.1007/BF01559085}}
3. ^{{cite journal|title = Über die Einwirkung von Jodmethyl auf Disulfide|first1 = W.|last1 = Steinkopf|first2 = S.|last2 = Müller|doi = 10.1002/cber.19230560834|journal = Chem. Ber.|volume = 56|issue = 8|pages =1926–1930|year = 1923}}
4. ^{{cite journal|year = 1941|volume = 29|issue = 17|pages = 256|title = Trimethylammoniumjodid und Trimethylsulfoniumjodid|last = Mussgnug|first = F.|journal = Naturwissenschaften|doi = 10.1007/BF01479158}}
5. ^{{cite journal|last1=Zuccaro|first1=D. Ε.|last2=McCullough|first2=J. D.|title=The crystal structure of trimethylsulfonium iodide|journal=Zeitschrift für Kristallographie - Crystalline Materials|date=1 January 1959|volume=112|issue=1-6|doi=10.1524/zkri.1959.112.jg.401}}
6. ^{{cite web|title=Trimethylsulfonium tetrafluoroborate|url=http://www.sigmaaldrich.com/catalog/product/aldrich/740489|publisher=Sigma-Aldrich|accessdate=23 September 2016}}
7. ^{{cite web|title=Trimethylsulfonium methyl sulfate|url=http://www.sigmaaldrich.com/catalog/product/aldrich/303593|publisher=Sigma-Aldrich|accessdate=23 September 2016}}
8. ^{{cite journal|last1=Ma|first1=M.|last2=Johnson|first2=K.E.|title=Some physicochemical characteristics of molten salts derived from trimethylsulfonium bromide|journal=Canadian Journal of Chemistry|date=April 1995|volume=73|issue=4|pages=593–598|doi=10.1139/v95-076}}

See also

  • Onium compounds

2 : Cations|Sulfur ions

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