Several salts of trimethylsulfonium are known. X-ray crystallography reveals that the ion has trigonal pyramidal molecular geometry at sulfur atom, with C-S-C angles near 102° and C-S bond distance of 177 picometers. Unless the counteranion is colored, all trimethylsulfonium salts are white or colorless.
melting point = 92-94 °C[8] Crystal structure orthorhombic with these parameters: a = 12.6157 μm, b = 8.2419 μm, c = 7.540 μm cell volume 784.0 2 formulas per unit cell[clarification needed]
^Knop, Osvald; Cameron, T. Stanley; Bakshi, Pradip K.; Linden, Antony; Roe, Stephen P. (1994). "Crystal chemistry of tetraradial species. Part 5. Interaction Between Cation Lone Pairs and Phenyl Groups in Tetraphenylborates: Crystal Structures of Me3S+,Et3S+, Me3SO+, Ph2I+, and 1-Azoniapropellane Tetraphenylborates". Canadian Journal of Chemistry. 72 (8): 1870–1881. doi:10.1139/v94-238.
^Heilbron's Dictionary of Organic Compounds, volume 4, revised edition published in 1953. Published in Great Britain
^Blättler, H. (1919). "Über Trimethylsulfoniumverbindungen". Monatshefte für Chemie und verwandte Teile anderer Wissenschaften. 40 (8): 417–429. doi:10.1007/BF01559085. S2CID 197766904.
^ abSteinkopf, W.; Müller, S. (1923). "Über die Einwirkung von Jodmethyl auf Disulfide". Chem. Ber.56 (8): 1926–1930. doi:10.1002/cber.19230560834.
^Mussgnug, F. (1941). "Trimethylammoniumjodid und Trimethylsulfoniumjodid". Naturwissenschaften. 29 (17): 256. Bibcode:1941NW.....29..256M. doi:10.1007/BF01479158. S2CID 33842580.
^Zuccaro, D. Ε.; McCullough, J. D. (1 January 1959). "The crystal structure of trimethylsulfonium iodide". Zeitschrift für Kristallographie - Crystalline Materials. 112 (1–6): 401–408. doi:10.1524/zkri.1959.112.jg.401. S2CID 98338161.
^"Trimethylsulfonium tetrafluoroborate". Sigma-Aldrich. Retrieved 23 September 2016.
^"Trimethylsulfonium methyl sulfate". Sigma-Aldrich. Retrieved 23 September 2016.
^Ma, M.; Johnson, K.E. (April 1995). "Some physicochemical characteristics of molten salts derived from trimethylsulfonium bromide". Canadian Journal of Chemistry. 73 (4): 593–598. doi:10.1139/v95-076.
trimethylsulfonium, systematically, named, trimethylsulfanium, organic, cation, with, chemical, formula, also, written, c3h9s, namesiupac, name, systematic, iupac, name, trimethylsulfaniumother, names, trimesiumtrimethylsulfur, identifierscas, number, model, j. Trimethylsulfonium systematically named trimethylsulfanium is an organic cation with the chemical formula CH3 3S also written as C3H9S Trimethylsulfonium NamesIUPAC name TrimethylsulfoniumSystematic IUPAC name TrimethylsulfaniumOther names TrimesiumTrimethylsulfur 1 IdentifiersCAS Number 676 84 6 Y3D model JSmol Interactive imageChemSpider 1115PubChem CID 1147UNII 8U5M0SJV65 YInChI InChI 1S C3H9S c1 4 2 3 h1 3H3 q 1Key NRZWQKGABZFFKE UHFFFAOYSA NSMILES C S C CPropertiesChemical formula CH3 3S Molar mass 77 17 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 Compounds 2 Preparation 3 Related 4 Use 5 References 6 See alsoCompounds edit nbsp Structure of CH3 3S in its tetraphenylborate salt 1 Several salts of trimethylsulfonium are known X ray crystallography reveals that the ion has trigonal pyramidal molecular geometry at sulfur atom with C S C angles near 102 and C S bond distance of 177 picometers Unless the counteranion is colored all trimethylsulfonium salts are white or colorless Salt Formula Molecular weight g mol Properties 2 Trimethylsulfonium chloride CH3 3S Cl 112 5 Colorless crystals decompose at 100 C very soluble in ethanol very hygroscopic 3 Trimethylsulfonium bromide CH3 3S Br 157 Colorless crystals Decomposes at 172 C melts in a sealed tube at 201 201 C reacts in neutral aqueous solution clarification needed 4 Trimethylsulfonium iodide CH3 3S I 204 Colorless crystals decomposes at 203 207 C 4 5 crystal structure monoclinic with these parameters a 5 94 mm b 8 00 mm c 8 92 mm b 126 32 2 formulas per unit cell clarification needed density 1 958 g cm3 6 Trimethylsulfonium tetrafluoroborate CH3 3S BF4 163 97 melting point 205 210 C 7 Trimethylsulfonium methylsulfate CH3 3S CH3OSO 3 188 27 melting point 92 94 C 8 Crystal structure orthorhombic with these parameters a 12 6157 mm b 8 2419 mm c 7 540 mm cell volume 784 0 2 formulas per unit cell clarification needed Preparation editSulfonium 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 2S CH3I CH3 3S I Related editAn extra oxygen atom can bond to the sulfur atom to yield the trimethylsulfoxonium ion CH3 3S O where the sulfur atom is tetravalent and tetracoordinated Use editGlyphosate herbicide is often supplied as a trimethylsulfonium salt referred to as trimesium 9 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 10 References edit Knop Osvald Cameron T Stanley Bakshi Pradip K Linden Antony Roe Stephen P 1994 Crystal chemistry of tetraradial species Part 5 Interaction Between Cation Lone Pairs and Phenyl Groups in Tetraphenylborates Crystal Structures of Me3S Et3S Me3SO Ph2I and 1 Azoniapropellane Tetraphenylborates Canadian Journal of Chemistry 72 8 1870 1881 doi 10 1139 v94 238 Heilbron s Dictionary of Organic Compounds volume 4 revised edition published in 1953 Published in Great Britain Blattler H 1919 Uber Trimethylsulfoniumverbindungen Monatshefte fur Chemie und verwandte Teile anderer Wissenschaften 40 8 417 429 doi 10 1007 BF01559085 S2CID 197766904 a b Steinkopf W Muller S 1923 Uber die Einwirkung von Jodmethyl auf Disulfide Chem Ber 56 8 1926 1930 doi 10 1002 cber 19230560834 Mussgnug F 1941 Trimethylammoniumjodid und Trimethylsulfoniumjodid Naturwissenschaften 29 17 256 Bibcode 1941NW 29 256M doi 10 1007 BF01479158 S2CID 33842580 Zuccaro D E McCullough J D 1 January 1959 The crystal structure of trimethylsulfonium iodide Zeitschrift fur Kristallographie Crystalline Materials 112 1 6 401 408 doi 10 1524 zkri 1959 112 jg 401 S2CID 98338161 Trimethylsulfonium tetrafluoroborate Sigma Aldrich Retrieved 23 September 2016 Trimethylsulfonium methyl sulfate Sigma Aldrich Retrieved 23 September 2016 Glyphosate trimesium PubChem Ma M Johnson K E April 1995 Some physicochemical characteristics of molten salts derived from trimethylsulfonium bromide Canadian Journal of Chemistry 73 4 593 598 doi 10 1139 v95 076 See also editOnium compounds Retrieved from https en wikipedia org w index php title Trimethylsulfonium amp oldid 1198056352, wikipedia, wiki, book, books, library,
