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{{refimprove|date=July 2011}} |
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| verifiedrevid = 443855839 |
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| verifiedrevid = 444964107 |
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| ImageFileL1 = hexafluorobenzene.svg |
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| ImageFileL1 = hexafluorobenzene.svg |
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| ImageSizeL1 = 120px |
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| ImageSizeL1 = 120 |
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| ImageNameL1 = Skeletal formula of hexafluorobenzene |
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| ImageAltL1 = Skeletal formula of hexafluorobenzene |
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| ImageFileR1 = Hexafluorobenzene-3D-balls.png |
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| ImageFileR1 = Hexafluorobenzene 3D spacefill.png |
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| ImageSizeR1 = 120px |
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| ImageSizeR1 = 130 |
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| ImageNameR1 = Ball-and-stick model of hexafluorobenzene |
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| ImageAltR1 = Space-filling model of hexafluorobenzene |
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| IUPACName = Hexafluorobenzene |
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| PIN = Hexafluorobenzene |
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| OtherNames = Perfluorobenzene |
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| OtherNames = Perfluorobenzene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 392-56-3 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Abbreviations = HFB |
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| Beilstein = 1683438 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13836549 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 38589 |
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| EC_number = 206-876-2 |
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| Gmelin = 101976 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = CMC18T611K |
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| SMILES = Fc1c(F)c(F)c(F)c(F)c1F |
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| SMILES = Fc1c(F)c(F)c(F)c(F)c1F |
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| InChI = 1/C6F6/c7-1-2(8)4(10)6(12)5(11)3(1)9 |
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| InChI = 1/C6F6/c7-1-2(8)4(10)6(12)5(11)3(1)9 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZQBFAOFFOQMSGJ-UHFFFAOYSA-N |
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| StdInChIKey = ZQBFAOFFOQMSGJ-UHFFFAOYSA-N |
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| CASNo = 392-56-3 |
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| CASNo_Ref = {{cascite|correct|CAS}}= |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13836549 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 38589 |
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| RTECS = |
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| EC-number = |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=6|F=6 |
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| C=6 | F=6 |
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| Appearance = Colorless liquid |
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| Appearance = Colorless liquid |
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| Density = 1.6120 g/cm<sup>3</sup> |
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| Density = 1.6120 g/cm<sup>3</sup> |
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| Solubility = |
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| Solubility = |
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| MeltingPtC = 5.2 |
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| MeltingPtC = 5.2 |
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| BoilingPtC = 80.1 |
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| BoilingPtC = 80.3 |
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| BoilingPt_ref = <ref name=Ullmann>{{Ullmann|title=Fluorine compounds, organic|first1=Günter|last1=Siegemund|first2=Werner|last2=Schwertfeger|first3=Andrew|last3=Feiring|first4=Bruce|last4=Smart|first5=Fred|last5=Behr|first6=Herward|last6=Vogel|first7=Blaine|last7=McKusick|first8=Peer|last8=Kirsch|doi=10.1002/14356007.a11_349.pub2|year=2016|p=44}}</ref> |
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| pKa = |
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| pKa = |
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| Viscosity = ] (1.200 mPa•s) (20 °C) |
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| Viscosity = ] (1.200 mPa•s) (20 °C) |
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| Dipole = 0.00 ] (gas) |
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| Dipole = 0.00 ] (gas) |
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| RefractIndex = 1.377 |
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| RefractIndex = 1.377 |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| FlashPtC = 10 |
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| FlashPt = 10 °C<ref>Across Organics:Catalog of fine Chimcals (1999)</ref> |
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| FlashPt_ref = <ref>Acros Organics:Catalog of fine Chemicals (1999)</ref> |
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| EUClass = Highly Flammable ('''F''') |
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| NFPA-H = |
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| NFPA-H = |
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| NFPA-F = |
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| NFPA-F = |
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| NFPA-R = |
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| NFPA-R = |
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| Autoignition = |
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| AutoignitionPt = |
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| Hazards_ref = <ref>{{cite web |title=Hexafluorobenzene 99% |url=https://www.sigmaaldrich.com/AU/en/product/aldrich/h8706?context=product |publisher=Sigma Aldrich}}</ref> |
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| RPhrases = {{R11}} |
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| GHSPictograms = {{GHS02}} |
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| SPhrases = {{S33}} {{S29}} {{S9}} {{S16}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|225}} |
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| PPhrases = {{P-phrases|210|233|240|241|242|243}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| Function = |
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| OtherFunction_label = |
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| OtherCompounds = ]<br />]<br />]<br />] |
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| OtherCpds = ], ]}} |
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'''Hexafluorobenzene''', HFB, {{chem|C|6|F|6}}, or '''perfluorobenzene''' is an ], ] ]. In this derivative of ] all ] atoms have been replaced by fluorine atoms. The technical uses of the compound are limited, although it is recommended as a ] in a number of ] reactions. In the laboratory hexafluorobenzene is used for several purposes: |
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'''Hexafluorobenzene''', HFB, {{chem|C|6|F|6}}, or '''perfluorobenzene''' is an ]. In this derivative of ], all ] atoms have been replaced by fluorine atoms. The technical uses of the compound are limited, although it has some specialized uses in the laboratory owing to distinctive spectroscopic properties. |
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* standard in ] |
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* solvent and standard in ] |
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* solvent in ] |
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* solvent when studying some parts in the ] |
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* solvent in ], as hexafluorobenzene itself hardly shows any absorbance in the UV region. |
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== Geometry of the aromatic ring == |
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== Geometry of the aromatic ring == |
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Hexafluorobenzene stands somewhat aside in the perhalogenbenzenes. If a perhalogenated benzene ring were to remain planar, then geometric constraints would force adjacent halogens closer than their associated nonbonding radius. Consequently the benzene ring buckles, reducing ] overlap and aromaticity to avoid the steric clash. Perfluorobenzene is an exception: as shown in the following table, two fluorines are small enough to avoid collision, retaining planarity and full aromaticity.<ref>{{cite journal |last1=Delorme |first1=P. |last2=Denisselle |first2=F. |last3=Lorenzelli |first3=V. |date=1967 |title=Spectre infrarouge et vibrations fondamentales des dérivés hexasubstitués halogénés du benzène |trans-title=Infrared spectrum and fundamental vibrations of the hexasubstituted halogen derivatives of benzene |journal=Journal de Chimie Physique |language=French |volume=64 |pages=591–600 |doi=10.1051/jcp/1967640591|bibcode=1967JCP....64..591D }}</ref> |
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Hexafluorobenzene in the perhalogenbenzenes stands somewhat aside. When counting for bond angles and distances it is possible to calculate the distance between two ortho fluorine atoms. Also the non bonding radius of the halogens is known. The following table presents the results:<ref>P. Delorme, F. Denesselle: J. Chem. Phys., jaargang 64, pagina 591 (1967).</ref> |
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{| class="wikitable" width="60%" |
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{| class="wikitable" |
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! style="width:20%;" | Formula |
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! Formula |
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! style="width:20%;" | Name |
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! Name |
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! style="width:20%;" | Calculated<br />inter-halogen<br />distance, aromatic ring assumed planar |
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! Inter-halogen distance (if planar) |
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! Nonbonding radius×2 |
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! style="width:20%;" | Twice nonbonding radius |
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! style="width:20%;" | Consequent symmetry of the benzene |
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! Consequent symmetry |
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| C<sub>6</sub>F<sub>6</sub> || perfluorobenzene || 279 || 270 || D<sub>6h</sub> |
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| C<sub>6</sub>F<sub>6</sub> || Hexafluorobenzene || 279 || 270 || D<sub>6h</sub> |
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| C<sub>6</sub>Cl<sub>6</sub> || ] || 312 || 360 || D<sub>3d</sub> |
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| C<sub>6</sub>Cl<sub>6</sub> || ] || 312 || 360 || D<sub>3d</sub> |
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| C<sub>6</sub>Br<sub>6</sub> || ] || 327 || 390 || D<sub>3d</sub> |
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| C<sub>6</sub>Br<sub>6</sub> || ] || 327 || 390 || D<sub>3d</sub> |
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| C<sub>6</sub>I<sub>6</sub> || ] || 354 || 430 || D<sub>3d</sub> |
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| C<sub>6</sub>I<sub>6</sub> || ] || 354 || 430 || D<sub>3d</sub> |
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The conclusion of the table is HFB is the only perhalobenzene being planar, the others all are buckled more or less. As a consequence in C<sub>6</sub>F<sub>6</sub> the overlap between the ] is optimal, while in the others it is less, also giving rise to a lower aromaticity in those compounds. |
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== Synthesis == |
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== Synthesis == |
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The direct synthesis of hexafluorobenzene from ] and ] is not possible. The synthetic route proceeds via the reaction of ]-] with ]ated benzene:<ref>N. N. Vorozhtsov, V. E. Platonov, G. G. Yakobson: "Preparation of hexafluorobenzene from hexachlorobenzene", '']'', '''1963''', ''12'' (8), p. 1389; {{DOI|10.1007/BF00847820}}.</ref> |
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The direct synthesis of hexafluorobenzene from ] and ] has not been useful. Instead it is prepared by the reaction of ] ] with ]ated benzene:<ref>{{cite journal |last1=Vorozhtsov |first1=N. N. Jr. |last2=Platonov |first2=V. E. |last3=Yakobson |first3=G. G. |date=1963 |title=Preparation of hexafluorobenzene from hexachlorobenzene |journal=Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science |volume=12 |issue=8 |page=1389 |doi=10.1007/BF00847820}}</ref> |
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: C<sub>6</sub>Cl<sub>6</sub> + 6 KF → C<sub>6</sub>F<sub>6</sub> + 6 KCl |
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: C<sub>6</sub>Cl<sub>6</sub> + 6 KF → C<sub>6</sub>F<sub>6</sub> + 6 KCl |
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] instead adds to the ring, breaking aromaticity.<ref name=KO/>{{rp|861}} |
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In principle, various ] pyrolyze to hexafluorobenzene, but commercialization was still in the initial stages in 2000.<ref name=KO2/>{{rp|21}}{{needs update|date=July 2024}} |
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== Fluorine and the aromatic ring == |
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A substantial part of the chemistry of HFB is related to the position of fluorine in the periodic table. On its position at the end of the first row, fluorine is a halogen. It also is the smallest one, so taking up an electron releases the largest amount of energy of all elements, it is the strongest oxidant, it has the highest ]. The carbon fluorine bond therefore is highly polarized: the carbon atom has (partially) positive charge, fluorine negative. This reasoning holds very much for the electrons in the ]. Electrons in ] encounter a totally different situation. The ''p''-orbital at fluorine parallel to the one on the adjacent carbon will face an optimal interaction. Thereby fluorine, unlike the higher halogens, has no extra nodal plane in its orbitals, so size and geometry fit perfectly and no anti-bonding interactions occur. The dipole resulting from the σ-electronegativity will force a partial replacement of electric charge from fluorine towards carbon and the aromatic ring: fluorine behaves as a σ-electronegative, but as a π-electropositive element. This view is supported by the reactions C<sub>6</sub>F<sub>6</sub> exhibits. |
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== Reactions == |
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== Reactions == |
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Hexafluorobenzene easily undergoes ].<ref name=KO>{{Kirk-Othmer|doi=10.1002/0471238961.0914201802011026.a01.pub2|volume=11|title=Fluorine compounds, organic|first=William X.|last=Bajzer}}</ref>{{rp|866}}<ref name=KO2>{{Kirk-Othmer|doi=10.1002/0471238961.0612211502152104.a01|title=Fluorinated aromatic compounds|first=Max M.|last=Boudakian}}</ref>{{rp|pp=19-21}} One example is its reaction with sodium hydrosulfide to afford ]:<ref>{{cite journal |last1=Robson |first1=P. |last2=Stacey |first2=M. |last3=Stephens |first3=R. |last4=Tatlow |first4=J. C. |date=1960 |title=Aromatic polyfluoro-compounds. Part VI. Penta- and 2,3,5,6-tetra-fluorothiophenol |journal=Journal of the Chemical Society |issue=4 |pages=4754–4760 |doi=10.1039/JR9600004754}}</ref> |
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With regard to its reactions, HFB stands apart from other aromatic compounds. One of the main reactions of aromatics is ] which for C<sub>6</sub>F<sub>6</sub> is impossible. During the reaction a particle initially bonded to the aromatic nucleus leaves the molecule as a positive charge ion. In benzene, this is a H<sup>+</sup>-ion. In hexafluorobenzene a positive charged fluorine atom should have to leave, which does not occur. The vast number of reactions of HFB proceed with fluoride—negative charged—as leaving group. As a consequence the entering group also should be an anion. |
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:C<sub>6</sub>F<sub>6</sub> + NaSH → C<sub>6</sub>F<sub>5</sub>SH + NaF |
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The further reaction of pentafluorophenyl derivatives has long been puzzling, because the non-fluorine substituent has no effect. The second new substituent is always directed ], to form a 1,4-disubstituted-2,3,5,6-tetrafluorobenzene.{{cn|date=July 2024}} |
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Hexafluorobenzene is thus a ] in certain ] heat-resistant ]s' synthesis.<ref>{{Kirk-Othmer|p=18|doi=10.1002/0471238961.0805012003011919.a01|title=Heat-resistant polymers|first1=Patrick E.|last1=Cassidy|first2=Tejraj M.|last2=Aminabhavi|first3=V. Sreenivasulu|last3=Reddy}}</ref> |
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UV light causes gaseous HFB to isomerize to hexafluoro derivative of ].<ref>{{cite journal |doi=10.1021/ar960057j|title=Hexafluorobenzene Photochemistry: Wellspring of Fluorocarbon Structures |year=2001 |last1=Lemal |first1=David M. |journal=Accounts of Chemical Research |volume=34 |issue=8 |pages=662–671 |pmid=11513574 }}</ref> |
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== Laboratory applications == |
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Hexafluorobenzene has been used as a reporter molecule to investigate tissue oxygenation in vivo. It is exceedingly hydrophobic, but exhibits high gas solubility with ideal liquid gas interactions. Since molecular oxygen is paramagnetic it causes <sup>19</sup>F NMR spin lattice relaxation (R1): specifically a linear dependence R1= a + bpO<sub>2</sub> has been reported.<ref>{{cite book |last1=Zhao |first1=D. |last2=Jiang |first2=L. |last3=Mason |first3=R. P. |date=2004 |chapter=Measuring changes in tumor oxygenation |editor-last=Conn |editor-first=P. M. |title=Imaging in Biological Research, Part B |series=Methods in Enzymology |volume=386 |publisher=Elsevier |pages=378–418 |doi=10.1016/S0076-6879(04)86018-X |pmid=15120262 |isbn=978-0-12-182791-5}}</ref> HFB essentially acts as molecular amplifier, since the solubility of oxygen is greater than in water, but thermodynamics require that the pO2 in the HFB rapidly equilibrates with the surrounding medium. HFB has a single narrow <sup>19</sup>F NMR signal and the spin lattice relaxation rate is highly sensitive to changes in pO<sub>2</sub>, yet minimally responsive to temperature. HFB is typically injected directly into a tissue and <sup>19</sup>F NMR may be used to measure local oxygenation. It has been extensively applied to examine changes in tumor oxygenation in response to interventions such as breathing hyperoxic gases or as a consequence of vascular disruption.<ref>{{cite journal |last1=Zhao |first1=D. |last2=Jiang |first2=L. |last3=Hahn |first3=E. W. |last4=Mason |first4=R. P. |date=2005 |title=Tumor physiologic response to combretastatin A4 phosphate assessed by MRI |journal=International Journal of Radiation Oncology, Biology, Physics |volume=62 |issue=3 |pages=872–880 |doi=10.1016/j.ijrobp.2005.03.009|pmid=15936572 }}</ref> MRI measurements of HFB based on 19F relaxation have been shown to correlate with radiation response of tumors.<ref>{{cite journal |last1=Zhao |first1=D. |last2=Constantinescu |first2=A. |last3=Chang |first3=C.-H. |last4=Hahn |first4=E. W. |last5=Mason |first5=R. P. |date=2003 |title=Correlation of tumor oxygen dynamics with radiation response of the Dunning prostate R3327-HI tumor |journal=Radiation Research |volume=159 |issue=5 |pages=621–631 |doi=10.1667/0033-7587(2003)1592.0.CO;2|pmid=12710873 }}</ref> HFB has been used as a gold standard for investigating other potential prognostic biomarkers of tumor oxygenation such as BOLD (Blood Oxygen Level Dependent),<ref>{{cite journal |last1=Zhao |first1=D. |last2=Jiang |first2=L. |last3=Hahn |first3=E. W. |last4=Mason |first4=R. P. |date=2009 |title=Comparison of <sup>1</sup>H blood oxygen level–dependent (BOLD) and <sup>19</sup>F MRI to investigate tumor oxygenation |journal=Magnetic Resonance in Medicine |volume=62 |issue=2 |pages=357–364 |doi=10.1002/mrm.22020 |doi-access=free |pmc=4426862 |pmid=19526495}}</ref> TOLD (Tissue Oxygen Level Dependent) <ref>{{cite journal |last1=Hallac |first1=R. R. |last2=Zhou |first2=H. |last3=Pidikiti |first3=R. |last4=Song |first4=K. |last5=Stojadinovic |first5=S. |last6=Zhao |first6=D. |last7=Solberg |first7=T. |last8=Peschke |first8=P. |last9=Mason |first9=R. P. |date=2014 |title=Correlations of noninvasive BOLD and TOLD MRI with pO<sub>2</sub> and relevance to tumor radiation response |journal=Magnetic Resonance in Medicine |volume=71 |issue=5 |pages=1863–1873 |doi=10.1002/mrm.24846 |doi-access=free |pmc=3883977 |pmid=23813468}}</ref> and MOXI (MR oximetry) <ref>{{cite journal |last1=Zhang |first1=Z. |last2=Hallac |first2=R. R. |last3=Peschke |first3=P. |last4=Mason |first4=R. P. |date=2014 |title=A noninvasive tumor oxygenation imaging strategy using magnetic resonance imaging of endogenous blood and tissue water |journal=Magnetic Resonance in Medicine |volume=71 |issue=2 |pages=561–569 |doi=10.1002/mrm.24691 |doi-access=free |pmc=3718873 |pmid=23447121}}</ref> A 2013 review of applications has been published.<ref>{{cite journal |last1=Yu |first1=J.-X. |last2=Hallac |first2=R. R. |last3=Chiguru |first3=S. |last4=Mason |first4=R. P. |date=2013 |title=New frontiers and developing applications in <sup>19</sup>F NMR |journal=Progress in Nuclear Magnetic Resonance Spectroscopy |volume=70 |pages=25–49 |doi=10.1016/j.pnmrs.2012.10.001 |pmc=3613763 |pmid=23540575}}</ref> |
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HFB has been evaluated as standard in ] spectroscopy.<ref>{{cite journal |doi=10.1002/anie.201802620|title=Exposing the Origins of Irreproducibility in Fluorine NMR Spectroscopy |year=2018 |last1=Rosenau |first1=Carl Philipp |last2=Jelier |first2=Benson J. |last3=Gossert |first3=Alvar D. |last4=Togni |first4=Antonio |journal=Angewandte Chemie International Edition |volume=57 |issue=30 |pages=9528–9533 |pmid=29663671 }}</ref> |
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==Toxicity== |
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Hexafluorobenzene may cause eye and ], respiratory and digestive tract irritation and can cause ] per ].<ref>{{cite web |url=https://fscimage.fishersci.com/msds/24032.htm |title=Material safety data sheet: Hexafluorobenzene, 99% |author=<!--Not stated--> |date=n.d. |website=Fisher Scientific |publisher=Thermo Fisher Scientific |access-date=2020-02-08}}</ref> |
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The ] (NIOSH) lists it in its ] as ]. |
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==See also== |
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The reaction of pentafluorophenyl derivatives has been long puzzling for its mechanism. Independent of the substituent, they all exhibit an ]. The new introduced group too has no effect on the directing behaviour. In all cases, a 1,4-disubstituted-2,3,5,6-tetrafluorobenzene derivative shows up. Finally, the clue is found not in the nature of the non-fluorine substituent, but in the fluorines themselves. The π-electropositive effect introduces electrons into the aromatic ring. The non-fluorine substituent is not capable of doing so. As charge accumulates at the ''ortho'' and ''para'' positions relative to the donating group, the ''ortho'' and ''para''-positions relative to the non-fluorine substituent receive less charge, so are less negative or more positive. Furthermore the non-fluorine substituent in general is more bulky than fluorine, so its ''ortho''-positions are sterically shielded, leaving the ''para''-position as the sole reaction site for anionic entering groups. |
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== References == |
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== References == |
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{{reflist}} |
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{{reflist|2}} |
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== Further reading== |
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* {{cite journal |last1=Pummer |first1=W. J. |last2=Wall |first2=L. A. |date=1958 |title=Reactions of hexafluorobenzene |journal=Science |volume=127 |issue=3299 |pages=643–644 |doi=10.1126/science.127.3299.643|pmid=17808882 |bibcode=1958Sci...127..643P }} |
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* {{cite patent |country=US |number=3277192 |status=patent |title=Preparation of hexafluorobenzene and fluorochlorobenzenes |gdate=1966-10-04 |fdate=1963-12-11 |pridate=1962-12-19 |invent1=Fielding, H. C. |assign=Imperial Chemical Industries}} |
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* {{cite journal |last1=Bertolucci |first1=M. D. |last2=Marsh |first2=R. E. |date=1974 |title=Lattice parameters of hexafluorobenzene and 1,3,5-trifluorobenzene at −17 °C |journal=Journal of Applied Crystallography |volume=7 |issue=1 |pages=87–88 |doi=10.1107/S0021889874008764|bibcode=1974JApCr...7...87B }} |
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* {{cite journal |last1=Samojłowicz |first1=C. |last2=Bieniek |first2=M. |last3=Pazio |first3=A. |last4=Makal |first4=A. |last5=Woźniak |first5=K. |last6=Poater |first6=A. |last7=Cavallo |first7=L. |last8=Wójcik |first8=J. |last9=Zdanowski |first9=K. |last10=Grela |first10=K. |date=2011 |title=The doping effect of fluorinated aromatic solvents on the rate of ruthenium-catalysed olefin metathesis |journal=Chemistry: A European Journal |volume=17 |issue=46 |pages=12981–12993 |doi=10.1002/chem.201100160|pmid=21956694 }} |
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