Benzene, hexafluoro-

• Formula: C₆F₆
• Molecular weight: 186.0546
• IUPAC Standard InChI: InChI=1S/C6F6/c7-1-2(8)4(10)6(12)5(11)3(1)9 Copy

  
• IUPAC Standard InChIKey: ZQBFAOFFOQMSGJ-UHFFFAOYSA-N Copy
• CAS Registry Number: 392-56-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: CP 28; Hexafluorobenzene; Perfluorobenzene; 1,2,3,4,5,6-Hexafluorobenzene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Gas phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

 +  = ( • )

By formula: Cl^- + C₆F₆ = (Cl^- • C₆F₆)

C₆H₆⁺ +  = (C₆H₆⁺ • )

By formula: C₆H₆⁺ + C₆F₆ = (C₆H₆⁺ • C₆F₆)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆F₆ = (C₆H₇N⁺ • C₆F₆)

Bond type: Charge transfer bond (positive ion)

C₆F₆^- +  = (C₆F₆^- • )

By formula: C₆F₆^- + C₆F₆ = (C₆F₆^- • C₆F₆)

 +  = ( • )

By formula: F^- + C₆F₆ = (F^- • C₆F₆)

 +  = ( • )

By formula: I^- + C₆F₆ = (I^- • C₆F₆)

 +  = ( • )

By formula: Br^- + C₆F₆ = (Br^- • C₆F₆)

C₆F₆⁺ +  = (C₆F₆⁺ • )

By formula: C₆F₆⁺ + C₆F₆ = (C₆F₆⁺ • C₆F₆)

Bond type: Charge transfer bond (positive ion)

( • ) +  = ( • 2)

By formula: (Cl^- • C₆F₆) + C₆F₆ = (Cl^- • 2C₆F₆)

( • ) +  = ( • 2)

By formula: (I^- • C₆F₆) + C₆F₆ = (I^- • 2C₆F₆)

( • ) +  = ( • 2)

By formula: (Br^- • C₆F₆) + C₆F₆ = (Br^- • 2C₆F₆)

( • ) +  = ( • 2)

By formula: (F^- • C₆F₆) + C₆F₆ = (F^- • 2C₆F₆)

Au^- +  = C₆AuF₆^-

By formula: Au^- + C₆F₆ = C₆AuF₆^-

 +  = ( • )

By formula: Cr⁺ + C₆F₆ = (Cr⁺ • C₆F₆)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

UV/Visible spectrum

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Stewart, 2004
Stewart, J.J.P., Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation, J. Mol. Model, 2004, 10, 1, 6-10, https://doi.org/10.1007/s00894-003-0157-6 . [all data]

Cox, Gundry, et al., 1969
Cox, J.D.; Gundry, H.A.; Harrop, D.; Head, A.J., Thermodynamic properties of fluorine compounds. 9. Enthalpies of formation of some compounds containing the pentafluorophenyl group, J. Chem. Thermodyn., 1969, 1, 77-87. [all data]

Krech, Price, et al., 1972
Krech, M.; Price, S.J.W.; Yared, W.F., Determination of the heat of formation of hexafluorobenzene, Can. J. Chem., 1972, 50, 2935-2938. [all data]

Messerly and Finke, 1970
Messerly, J.F.; Finke, H.L., Hexafluorobenzene and 1,3-difluorobenzene. Low-temperature calorimetric studies and chemical thermodynamic properties, J. Chem. Thermodynam., 1970, 2, 867-880. [all data]

Counsell, Green, et al., 1965
Counsell, J.F.; Green, J.H.S.; Hales, J.L.; Martin, J.F., Thermodynamic properties of fluorine compounds. Part 2. Physical and thermodynamic properties of hexafluorobenzene, Trans. Faraday Soc., 1965, 61, 212-218. [all data]

Wilhelm, Lainez, et al., 1987
Wilhelm, E.; Lainez, A.; Berkane, M.; Roux-Desgranges, G.; Roux, A.H.; Grolier, J.-P.E., Hydrocarbon/fluorohydrocarbon solutions: thermodyanmic studies on an important class of materials, Calorim. Anal. Therm., 1987, 18, 95-99. [all data]

Gorbunova, Grigoriev, et al., 1982
Gorbunova, N.I.; Grigoriev, V.A.; Simonov, V.M.; Shipova, V.A., Heat capacity of liquid benzene and hexafluorobenzene at atmospheric pressure, Int. J. Thermophysics, 1982, 3, 1-15. [all data]

Gorbunova, Simonov, et al., 1982
Gorbunova, N.I.; Simonov, V.M.; Shipova, V.A., The enthalpy of benzene and hexafluorobenzene in the temperature range of 290-680 K and pressure range 0.1-20.0 MPa, Proc. Symp. Thermophys. Prop. 8th(2), 1982, 409-14. [all data]

Gorbunova, Simonov, et al., 1982, 2
Gorbunova, N.I.; Simonov, V.M.; Shipova, V.A., Thermodynamic properties of hexafluorobenzene, Dokl. Akad. Nauk, 1982, SSSR 266, 850-853. [all data]

Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P., Role of Binding Energies in A^-.B and A.B^- Complexes in the Kinetics of Gas Phase Electron Transfer Reactions:A^- + B = A + B^- Involving Perfluoro Compounds: SF₆, C₆F₁₁CF₃, J. Chem. Phys., 1986, 85, 9, 4989, https://doi.org/10.1063/1.451687 . [all data]

Hiraoka, Mizuse, et al., 1987
Hiraoka, K.; Mizuse, S.; Yamabe, S., High Symmetric Structure of the Gas Phase Ion Cluster X^-..C₆F6 (X = Cl, Br, I), J. Phys. Chem., 1987, 91, 20, 5294, https://doi.org/10.1021/j100304a032 . [all data]

Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H., Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies, J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034 . [all data]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Nakajima, Taguwa, et al., 1993
Nakajima, A.; Taguwa, T.; Hoshino, K.; Sugioka, T.; Naganuma, T.; Ono, F.; Watanabe, K.; Nakao, K., Photoelectron Spectroscopy of (C6F6)n- and (Au-C6F6)- Clusters, Chem. Phys. Lett., 1993, 214, 1, 22, https://doi.org/10.1016/0009-2614(93)85449-X . [all data]

Hiraoka, Mizuse, et al., 1990
Hiraoka, K.; Mizuse, S.; Yamabe, S., Stabilities and Structures of C6F6-(C6F6) and C6F6+(C6F6), J. Phys. Chem., 1990, 94, 9, 3689, https://doi.org/10.1021/j100372a061 . [all data]

Hiraoka, Mizuse, et al., 1987, 2
Hiraoka, K.; Mizuse, S.; Yamabe, S., A Determination of the Stability and Structure of F^-(C₆H₆) and F^-(C₆F₆) Clusters, J. Chem. Phys., 1987, 86, 7, 4102, https://doi.org/10.1063/1.451920 . [all data]

Ho and Dunbar, 1999
Ho, Y.P.; Dunbar, R.C., Reactions of Au+ and Au- with benzene and fluorine-substituted benzenes, Int. J. Mass Spectrom., 1999, 183, 175-184, https://doi.org/10.1016/S1387-3806(98)14245-8 . [all data]

Ryzhov, 1999
Ryzhov, V., Binding Energies of Chromium Cations with Fluorobenzenes from Radiative Association Kinetics, Int. J. Mass Spectrom., 1999, 185/186/187, 913. [all data]

Hitchcock, Fischer, et al., 1987
Hitchcock, H.P.; Fischer, P.; Gedanken, A.; Robin, M.B., Antibonding α valence MOs in the inner-shell and outer-shell spectra of the fluorobenzenes, J. Phys. Chem., 1987, 91, 531-540. [all data]

Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E., Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups, J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0 . [all data]

Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz., Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups, J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S . [all data]

Müller, Dietrich, et al., 1983
Müller, U.; Dietrich, P.; Prescher, D., Gaschromatographische Untersuchungen an Perfluor-Carbonverbindungen. II. Zur Gaschromatographischen Trennung von Gemischen Längerkettiger Perfluoralkane und Perfluoralkene, J. Chromatogr., 1983, 259, 243-254, https://doi.org/10.1016/S0021-9673(01)88005-5 . [all data]

Vernon and Edwards, 1975
Vernon, F.; Edwards, G.T., Gas-liquid chromatography on fluorinated stationary phases. I. Hydrocarbons and fluorocarbons, J. Chromatogr., 1975, 110, 1, 73-80, https://doi.org/10.1016/S0021-9673(00)91212-3 . [all data]

Brown, Chapman, et al., 1968
Brown, I.; Chapman, I.L.; Nicholson, G.J., Gas chromatography of polar solutes in electron acceptor stationary phases, Aust. J. Chem., 1968, 21, 5, 1125-1141, https://doi.org/10.1071/CH9681125 . [all data]

Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C., Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns, J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8 . [all data]

Zenkevich, 2008
Zenkevich, I.G., Experimental data, Personal communication, 2008. [all data]

Zenkevich, Eliseenkov, et al., 2006
Zenkevich, I.G.; Eliseenkov, E.V.; Kasatochkin, A.N., Application of Retention Indices in GC-MS Identification of Halogenated Organic Compounds, Mass Spectromery (Rus.), 2006, 3, 2, 131-140. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, References

• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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