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
  • Phase change data
  • Reaction thermochemistry data
  • Ion clustering data
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
• 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

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Reduced pressure boiling point

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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)

Ion clustering 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

Au^- +  = C₆AuF₆^-

By formula: Au^- + C₆F₆ = C₆AuF₆^-

 +  = ( • )

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

( • ) +  = ( • 2)

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

C₆F₆⁺ +  = (C₆F₆⁺ • )

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

Bond type: Charge transfer bond (positive ion)

C₆F₆^- +  = (C₆F₆^- • )

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

By formula: Cr⁺ + C₆F₆ = (Cr⁺ • C₆F₆)

 +  = ( • )

By formula: F^- + C₆F₆ = (F^- • C₆F₆)

( • ) +  = ( • 2)

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

 +  = ( • )

By formula: I^- + C₆F₆ = (I^- • C₆F₆)

( • ) +  = ( • 2)

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

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]

Messerly and Finke, 1970, 2
Messerly, J.F.; Finke, H.L., hexafluorobenzene and 1,3-difluorobenzene low temperature calorimetric studies and chemical thermodynamic properties, J. Chem. Thermodyn., 1970, 2, 867-80. [all data]

Paukov and Glukhikh, 1967
Paukov, I.E.; Glukhikh, L.K., Low temperature specific heats and absolute entropies of hexafluorobenzene and pentafluorochlorobenzene, Zh. Vses. Khim. O-va. im. D. I. Mendeleeva, 1967, 12, 236-7. [all data]

Counsell, Green, et al., 1965, 2
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. [all data]

Douslin, Harrison, et al., 1969
Douslin, D.R.; Harrison, R.H.; Moore, R.T., Pressure-Volume-Temperature Relations of Hexafluorobenzene, J. Chem. Thermodyn., 1969, 1, 305-19. [all data]

Hales and Townsend, 1974
Hales, J.L.; Townsend, R., Liquid Densities from 293 to 490 K of Eight Fluorinated Aromatic Comp., J. Chem. Thermodyn., 1974, 6, 111-6. [all data]

Mousa, Kay, et al., 1972
Mousa, A.H.N.; Kay, W.B.; Kreglewski, A., The critical constants of binary mixtures of certain perfluoro-compounds with alkanes, J. Chem. Thermodyn., 1972, 4, 301-11. [all data]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

PCR Inc., 1990
PCR Inc., Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Douslin and Osborn, 2002
Douslin, D.R.; Osborn, A., Pressure measurements in the 0.01-30 torr range with an inclined-piston gauge, J. Sci. Instrum., 2002, 42, 6, 369-373, https://doi.org/10.1088/0950-7671/42/6/301 . [all data]

Ambrose, Ewing, et al., 1990
Ambrose, D.; Ewing, M.B.; Ghiassee, N.B.; Sanchez Ochoa, J.C., The ebulliometric method of vapour-pressure measurement: vapour pressures of benzene, hexafluorobenzene, and naphthalene, The Journal of Chemical Thermodynamics, 1990, 22, 6, 589-605, https://doi.org/10.1016/0021-9614(90)90151-F . [all data]

Davies, Ewing, et al., 1988
Davies, D.R.; Ewing, M.B.; Hugill, J.A.; McGlashan, M.L., The critical temperature, the critical pressure, and the dependence of vapour pressure on temperature for dodecafluorocyclohexane and hexafluorobenzene, Can. J. Chem., 1988, 66, 4, 760-762, https://doi.org/10.1139/v88-131 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Patrick and Tomes, 1980
Patrick, C.R.; Tomes, F., The vapour pressures and excess free energies of mixing of the systems hexafluorobenzene-carbon tetrachloride and hexafluorobenzene-perfluoromethylcyclohexane, Journal of Fluorine Chemistry, 1980, 15, 4, 267-278, https://doi.org/10.1016/S0022-1139(00)81462-1 . [all data]

Findlay, 1969
Findlay, T.J.V., Vapor pressures of fluorobenzenes from 5 to 50.deg.C, J. Chem. Eng. Data, 1969, 14, 2, 229-231, https://doi.org/10.1021/je60041a012 . [all data]

Evans and Tiley, 1966
Evans, F.D.; Tiley, P.F., Vapour pressures and critical constants of hexafluoro-, pentafluoro-, chloropentafluoro-, and bromopentafluoro-benzene, J. Chem. Soc., B:, 1966, 134, https://doi.org/10.1039/j29660000134 . [all data]

Patrick and Prosser, 1964
Patrick, C.R.; Prosser, G.S., Vapour pressures and related properties of hexafluorobenzene and of pentafluorobenzene, Trans. Faraday Soc., 1964, 60, 700, https://doi.org/10.1039/tf9646000700 . [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Douslin, Harrison, et al., 1969, 2
Douslin, D.R.; Harrison, R.H.; Moore, R.T., Pressure-Volume-Temperature Relations of Hexafluorobenzene, J. Chem. Thermodyn., 1969, 1, 3, 305-319, https://doi.org/10.1016/0021-9614(69)90050-0 . [all data]

Douslin and Osborn, 1965
Douslin, D.R.; Osborn, A., Pressure Measurements in the 0·01-30 Torr with an Inclined-Piston Gauge, J. Sci. Instrum., 1965, 42, 6, 369-373, https://doi.org/10.1088/0950-7671/42/6/301 . [all data]

Scott and Osborn, 1979
Scott, D.W.; Osborn, A.G., Representation of vapor-pressure data, J. Phys. Chem., 1979, 83, 21, 2714-2723, https://doi.org/10.1021/j100484a007 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

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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]

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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]

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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]

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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]

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

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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

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• Symbols used in this document:
  

  Cp,liquid	Constant pressure heat capacity of liquid
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  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
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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