Triflidic acid (IUPAC name: tris[(trifluoromethyl)sulfonyl]methane, abbreviated formula: Tf3CH) is an organic superacid. It is one of the strongest known carbon acids and is among the strongest Brønsted acids in general, with an acidity exceeded only by the carborane acids. Notably, triflidic acid is estimated to have an acidity 104 times that of triflic acid (pKaaq ~ –14), as measured by its acid dissociation constant. It was first prepared in 1987 by Seppelt and Turowsky by the following route:[2]
In its anionic form, the lanthanide salts of triflidic acid ("triflides") have been shown to be more efficient Lewis acids than the corresponding triflates.[3][4] The triflide anion has also been employed as the anionic component of ionic liquids.[5]
^Barrett, A. G. M.; Braddock, D. C.; Raju, G. S. (2004). "Tris[(trifluoromethyl)sulfonyl]methane and Related Salts". In Charette, André; Bode, Jeffrey; Rovis, Tomislav; Shenvi, Ryan (eds.). Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn00441. ISBN9780470842898.
^Waller, Francis J.; Barrett, Anthony G. M.; Braddock, D. Christopher; Ramprasad, Dorai; McKinnell, R. Murray; White, Andrew J. P.; Williams, David J.; Ducray, Richard (1999-04-01). "Tris(trifluoromethanesulfonyl)methide ("Triflide") Anion: Convenient Preparation, X-ray Crystal Structures, and Exceptional Catalytic Activity as a Counterion with Ytterbium(III) and Scandium(III)". The Journal of Organic Chemistry. 64 (8): 2910–2913. doi:10.1021/jo9800917. ISSN 0022-3263. PMID 11674365.
^Ishihara, Kazuaki; Hiraiwa, Yukihiro; Yamamoto, Hisashi (2000-01-01). "Homogeneous Debenzylation Using Extremely Active Catalysts: Tris(triflyl)methane, Scandium(III) Tris(triflyl)methide, and Copper(II) Tris(triflyl)methide". Synlett. 2000 (1): 80–82. doi:10.1055/s-2000-6436. ISSN 0936-5214. S2CID 196771067.
^Johansson, Katarina M.; Adebahr, Josefina; Howlett, Patrick C.; Forsyth, Maria; MacFarlane, Douglas R. (2007-01-01). "N-Methyl-N-Alkylpyrrolidinium Bis(perfluoroethylsulfonyl)amide ([NPf2]) and Tris(trifluoromethanesulfonyl)methide ([CTf3]) Salts: Synthesis and Characterization". Australian Journal of Chemistry. 60 (1): 57–63. doi:10.1071/ch06299.
April 11, 2024
triflidic, acid, iupac, name, tris, trifluoromethyl, sulfonyl, methane, abbreviated, formula, tf3ch, organic, superacid, strongest, known, carbon, acids, among, strongest, brønsted, acids, general, with, acidity, exceeded, only, carborane, acids, notably, trif. Triflidic acid IUPAC name tris trifluoromethyl sulfonyl methane abbreviated formula Tf3CH is an organic superacid It is one of the strongest known carbon acids and is among the strongest Bronsted acids in general with an acidity exceeded only by the carborane acids Notably triflidic acid is estimated to have an acidity 104 times that of triflic acid pKaaq 14 as measured by its acid dissociation constant It was first prepared in 1987 by Seppelt and Turowsky by the following route 2 Triflidic acid NamesPreferred IUPAC name Bis trifluoromethanesulfonyl methanesulfonyl tri fluoro methaneOther names Triflidic acid tris triflyl methane tris trifluoromethyl sulfonyl methaneIdentifiersCAS Number 60805 12 1 Y3D model JSmol Interactive imageChemSpider 3512136 YECHA InfoCard 100 258 613PubChem CID 4306514CompTox Dashboard EPA DTXSID40401774InChI InChI 1S C4HF9O6S3 c5 2 6 7 20 14 15 1 21 16 17 3 8 9 10 22 18 19 4 11 12 13 h1HKey MYIAPBDBTMDUDP UHFFFAOYSA NSMILES H C S O C F F F O S O C F F F O S O C F F F OPropertiesChemical formula C4F9S3O6HMolar mass 412 23 g molAppearance Colorless solidMelting point 69 2 C 156 6 F 342 3 K Solubility in water MiscibleAcidity pKa 18 6 aqueous est 1 HazardsOccupational safety and health OHS OSH Main hazards Corrosive eye irritantGHS labelling PictogramsSignal word DangerHazard statements H314 H335Precautionary statements P260 P261 P264 P271 P280 P301 P330 P331 P303 P361 P353 P304 P340 P305 P351 P338 P310 P312 P321 P363 P403 P233 P405 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references 1 Tf2CH2 2CH3MgBr Tf2C MgBr 2 2CH4 2 Tf2C MgBr 2 TfF Tf3C MgBr MgBrF 3 Tf3C MgBr H2SO4 Tf3CH MgBrHSO4In its anionic form the lanthanide salts of triflidic acid triflides have been shown to be more efficient Lewis acids than the corresponding triflates 3 4 The triflide anion has also been employed as the anionic component of ionic liquids 5 See also editBistriflimide Non coordinating anionReferences edit Barrett A G M Braddock D C Raju G S 2004 Tris trifluoromethyl sulfonyl methane and Related Salts In Charette Andre Bode Jeffrey Rovis Tomislav Shenvi Ryan eds Encyclopedia of Reagents for Organic Synthesis doi 10 1002 047084289X rn00441 ISBN 9780470842898 Turowsky Lutz Seppelt Konrad 1988 06 01 Tris trifluoromethyl sulfonyl methane HC SO2CF3 3 Inorganic Chemistry 27 12 2135 2137 doi 10 1021 ic00285a025 ISSN 0020 1669 Waller Francis J Barrett Anthony G M Braddock D Christopher Ramprasad Dorai McKinnell R Murray White Andrew J P Williams David J Ducray Richard 1999 04 01 Tris trifluoromethanesulfonyl methide Triflide Anion Convenient Preparation X ray Crystal Structures and Exceptional Catalytic Activity as a Counterion with Ytterbium III and Scandium III The Journal of Organic Chemistry 64 8 2910 2913 doi 10 1021 jo9800917 ISSN 0022 3263 PMID 11674365 Ishihara Kazuaki Hiraiwa Yukihiro Yamamoto Hisashi 2000 01 01 Homogeneous Debenzylation Using Extremely Active Catalysts Tris triflyl methane Scandium III Tris triflyl methide and Copper II Tris triflyl methide Synlett 2000 1 80 82 doi 10 1055 s 2000 6436 ISSN 0936 5214 S2CID 196771067 Johansson Katarina M Adebahr Josefina Howlett Patrick C Forsyth Maria MacFarlane Douglas R 2007 01 01 N Methyl N Alkylpyrrolidinium Bis perfluoroethylsulfonyl amide NPf2 and Tris trifluoromethanesulfonyl methide CTf3 Salts Synthesis and Characterization Australian Journal of Chemistry 60 1 57 63 doi 10 1071 ch06299 Retrieved from https en wikipedia org w index php title Triflidic acid amp oldid 1176025702, wikipedia, wiki, book, books, library,
