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| verifiedrevid = 389050798 |
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|verifiedrevid = 437221912 |
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| Name = Triphenylmethyl Hexafluorophosphate |
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| ImageFile = Triphenylmethyl hexafluorophosphate.gif |
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|ImageFile = Ph3CPF6.png |
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| ImageSize = 4 KB |
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|ImageSize = 233 |
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|ImageFile2 = Triphenylmethyl-hexafluorophosphate-ion-pair-from-xtal-Mercury-3D-bs.png |
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| OtherNames = Trityl hexafluorophosphate<br/>Triphenylcarbenium hexafluorophosphate |
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|ImageSize2 = 200 |
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| Section1 = {{Chembox Identifiers |
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|ImageFile3 = Triphenylmethyl-hexafluorophosphate-xtal-packing-Mercury-3D-sf.png |
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| CASNo_Ref = {{cascite}} |
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|IUPACName = Triphenylcarbenium hexafluorophosphate |
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| CASNo = 437-17-2 |
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|SystematicName = Diphenylmethylbenzene hexafluoridophosphate |
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}} |
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|OtherNames = {{ubl|Triphenylcarbenium hexafluorophosphate(V)|Trityl hexafluorophosphate|Tritylium hexafluorophosphate}} |
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| Section2 = {{Chembox Properties |
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|Section1 = {{Chembox Identifiers |
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| Formula = C<sub>19</sub>H<sub>15</sub>F<sub>6</sub>P |
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|CASNo_Ref = {{cascite|correct|??}} |
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| MolarMass = 388.31 g/mol |
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|CASNo = 437-17-2 |
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| Appearance = brown powder |
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|ChemSpiderID = 2006130 |
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| Density = |
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|EINECS = 207-112-0 |
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| Solubility = |
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|PubChem = 2723954 |
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| MeltingPt = 145 °C |
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|SMILES = c1ccc(cc1)(c1ccccc1)c1ccccc1.F(F)(F)(F)(F)F |
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| BoilingPt = |
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|StdInChI=1S/C19H15.F6P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-7(2,3,4,5)6/h1-15H;/q+1;-1 |
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| Viscosity = |
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|StdInChIKey = IBTFOFOFRZKIJU-UHFFFAOYSA-N |
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| Section7 = {{Chembox Hazards |
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|Section2={{Chembox Properties |
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| ExternalMSDS = |
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|Formula = {{chem2|+−}} |
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| RPhrases = {{R34}}, {{R26}}, {{R36/37/39}}, {{R45}} |
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|C=19|H=15|F=6|P=1 |
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|Appearance = Brown powder |
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|MeltingPtC = 145 |
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|Section7={{Chembox Hazards |
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|ExternalSDS = |
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|GHSPictograms = {{GHS05}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|314}} |
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|PPhrases = {{P-phrases|260|264|280|301+330+331|303+361+353|304+340|305+351+338|310|321|363|405|501}} |
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'''Triphenylmethyl hexafluorophosphate''' (also '''triphenylcarbenium hexafluorophosphate''', '''trityl hexafluorophosphate''', or '''tritylium hexafluorophosphate''') is an organic ] with the formula {{chem2|+−}}, consisting of the ] ] {{chem2|+}} and the ] ] {{chem2|−}}.<ref name=PubChem>{{PubChem|2723954|Triphenylcarbenium hexafluorophosphate}}</ref> |
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'''Triphenylmethyl hexafluorophosphate''' is an ] with the formula C(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>PF<sub>6</sub>. This compound is a brown powder that is air sensitive and changes colors when exposed to light. Triphenylmethyl hexafluorophosphate is used as a ] and ] in organic syntheses.<ref name=Urch>{{cite journal |author=Urch, C. |title=Triphenylmethyl Hexafluorophosphate |journal=Encyclopedia of Reagents for Organic Synthesis |year=2001 |doi=10.1002/047084289X.rt363f}}</ref> |
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Triphenylmethyl hexafluorophosphate is a brown powder that hydrolyzes readily to ]. It is used as a ] and ] in organic syntheses.<ref name=Urch>{{cite journal |author=Urch, C. |title=Triphenylmethyl Hexafluorophosphate |journal=Encyclopedia of Reagents for Organic Synthesis |year=2001 |doi=10.1002/047084289X.rt363f|isbn=0471936235 }}</ref> |
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==Preparation== |
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Triphenylmethyl hexafluorophosphate is generated by two ways. The first method is by combining ] with ]:<ref>{{cite journal |author=Sharp, D., Shepard, N. |title=Complex Fluorides. Part VIII |journal=University Chemical Laboratory, Cambridge |year=1956 |pages=674–682}}</ref> |
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==Preparation== |
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:AgPF<sub>6</sub>+C(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>Cl→C(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>PF<sub>6</sub>+AgCl |
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Triphenylmethyl hexafluorophosphate can be prepared by combining ] with ]:<ref>{{cite journal |last1=Sharp |first1=D. W. A. |last2=Sheppard |first2=N. |title=Complex Fluorides. Part VIII. |journal=Journal of the Chemical Society (Resumed) |date=1957 |pages=674–682 |doi=10.1039/JR9570000674}}</ref> |
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The second method of generating triphenylmethyl hexafluorophosphate is through the reaction of ] with an ether complex of ]:<ref name=Olah>{{cite journal |title=Preparative Carbocation Chemistry; IV. Improved Preparation of Triphenylcarbenium (Trityl) Salts |journal=Synthesis |pages=544 |year=1972 |author=Olah, G., Svoboda, J., Olah, J.}}</ref> |
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:Ph<sub>3</sub>CCl+HPF<sub>6</sub>·O(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>→Ph<sub>3</sub>C<sup>+</sup>PF<sup>-</sup><sub>6</sub>+HCl+(C<sub>2</sub>H<sub>5</sub>)<sub>2</sub>O |
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:{{chem2|Ag+− + (C6H5)3CCl → +− + AgCl}} |
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Triphenylmethyl chloride is afforded by combining ] and ] in a ].<ref name=Olah/> |
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A second method involves protonolysis of triphenylmethanol:<ref>{{cite journal |title=Preparative Carbocation Chemistry; IV. Improved Preparation of Triphenylcarbenium (Trityl) Salts |journal=Synthesis |volume=1972 |issue=10 |pages=544 |year=1972 |author1=Olah, G. |author2=Svoboda, J. |author3=Olah, J. |doi= 10.1055/s-1972-21914}}</ref> |
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==Structure and Properties== |
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The ] group can exist in three oxidation states: trityl cation, trityl, and trityl anion. The trityl cation is the form present in triphenylmethyl hexafluorophosphate. The triphenylmethyl cation effectively has D3h ]. |
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:{{chem2|H + (C6H5)3COH → +− + H2O}} |
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The hexafluorophosphate of triphenylmethyl hexafluorophosphate readily undergoes ].<ref>{{cite journal |author=Fernandez-Galan, R.; Manzano, B; Otero, A; Lanfranchi, M; Pellinghelli, M. |title=<sup>19</sup>F and <sup>31</sup>P NMR Evidence for Silver Hexafluorophosphate Hydrolysis in Solution |journal=Inorg. Chem |volume=33 |pages=2309–2312 |year=1994 |doi=0020-+16691941+1333-2309�.50/0}}</ref> |
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==Structure and reactions== |
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CPh<sub>3</sub>PF<sub>6</sub>+H<sub>2</sub>O→HOCPh<sub>3</sub>+HPF<sub>6</sub> |
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Triphenylmethyl hexafluorophosphate readily ], in a reaction that is the reverse of one of its syntheses:<ref>{{cite journal |author1=Fernandez-Galan, R. |author2=Manzano, B |author3=Otero, A |author4=Lanfranchi, M |author5=Pellinghelli, M. |title=<sup>19</sup>F and <sup>31</sup>P NMR Evidence for Silver Hexafluorophosphate Hydrolysis in Solution |journal=Inorg. Chem. |volume=33 |issue=10 |pages=2309–2312 |year=1994 |doi=10.1021/ic00088a039}}</ref> |
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:{{chem2|+− + H2O → (C6H5)3COH + H}} |
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Triphenylmethyl hexafluorophosphate combined with water in basic conditions undergo hydrolysis to form ] and the conjugate acid hexafluorophosphoric acid. When acidic conditions are present, the reaction will proceed in the opposite direction and triphenyl methanol will form triphenylmethyl hexafluorophosphate and water. |
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Triphenylmethyl hexafluorophosphate has been used for abstracting ] ({{chem|H|-}}) from organic compounds. Treatment of ] and diene complexes one can generate ] and ]es, respectively.<ref name=Urch/> |
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==Main Reactions== |
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Triphenylmethyl hexafluorophosphate is used in hydride and alkoxy abstractions. For example, it has been used for abstracting hydride from transition metal alkene and diene complexes. For example, triphenylmethyl hexafluorophosphate can also ionize an alkoxy substituted and cyclopentadienyliron dicarbonyl complexes.<ref name=Urch/> Some examples are: |
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] is a common substitute for triphenylmethyl hexafluorophosphate. However, the perchlorate is not used as widely, because, like other organic perchlorates, it is potentially explosive.<ref name=Urch/> |
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Hydride Abstraction: |
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] |
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==See also== |
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Alkoxy Abstraction: |
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* ] |
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] |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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Triphenylmethyl perchlorate is a common substitute for triphenylmethyl hexafluorophosphate. However, perchlorate is not used as widely because it is an oxidizer with Cl having and ] of +7. Perchlorate readily combusts releasing Cl<sub>2</sub> and O<sub>2</sub> gas which is potentially explosive. Both triphenylmethyl hexafluorophosphate and triphenylmethyl perchlorate have shown similar results and yields in most reactions.<ref name=Urch/> |
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{{reflist}} |
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{{Hexafluorophosphates}} |
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==Footnotes== |
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<references/> |
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