Benzene, pentafluoro-

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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Δfgas-806.0 ± 1.4kJ/molCcrCox, Gundry, et al., 1969 

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

Quantity Value Units Method Reference Comment
Δfliquid-842.2 ± 1.4kJ/molCcrCox, Gundry, et al., 1969ALS
Quantity Value Units Method Reference Comment
Δcliquid-2557.0 ± 1.4kJ/molCcrCox, Gundry, et al., 1969ALS
Quantity Value Units Method Reference Comment
liquid279.49J/mol*KN/APaukov and Lavrent'eva, 1969DH
liquid275.9J/mol*KN/ACounsell, Hales, et al., 1968DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
210.79298.15Paukov and Lavrent'eva, 1969T = 12 to 300 K.; DH
204.7298.15Counsell, Hales, et al., 1968T = 12 to 324 K.; DH

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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
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

Quantity Value Units Method Reference Comment
Tboil358. ± 1.KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple225.67KN/APaukov and Lavrent'eva, 1969, 2Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple225.83KN/ACounsell, Hales, et al., 1968, 2Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc532.KN/AMajer and Svoboda, 1985 
Tc530.8KN/ASkripov and Muratov, 1977TRC
Tc530.96KN/AHales and Townsend, 1974Uncertainty assigned by TRC = 0.05 K; TRC
Tc530.97KN/AAmbrose and Sprake, 1971Uncertainty assigned by TRC = 0.03 K; TRC
Tc531.95KN/AEvans and Tiley, 1966Uncertainty assigned by TRC = 0.05 K; TRC
Quantity Value Units Method Reference Comment
Pc34.70barN/ASkripov and Muratov, 1977Vis, pc by extrapolation of VP; TRC
Pc35.31barN/AAmbrose and Sprake, 1971Uncertainty assigned by TRC = 0.05 bar; TRC
Pc35.16barN/AEvans and Tiley, 1966Uncertainty assigned by TRC = 0.10 bar; TRC
Quantity Value Units Method Reference Comment
ρc3.080mol/lN/AHales and Townsend, 1974Uncertainty assigned by TRC = 0.0030 mol/l; Liquid density determined by magnetically balanced float up to 490 K, see J.L.Hales, 1970-128. Critical D by equation due to Riedel.; TRC
Quantity Value Units Method Reference Comment
Δvap36.36kJ/molN/AMajer and Svoboda, 1985 
Δvap36.2kJ/molN/AInvernizzi, 1982Based on data from 290. to 510. K. See also Basarová and Svoboda, 1991.; AC
Δvap36.2 ± 0.2kJ/molVCox, Gundry, et al., 1969ALS
Δvap36.39kJ/molVFindlay, 1969ALS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
32.15358.9N/AMajer and Svoboda, 1985 
33.5373.AStephenson and Malanowski, 1987Based on data from 358. to 397. K.; AC
32.6408.AStephenson and Malanowski, 1987Based on data from 393. to 479. K.; AC
32.2488.AStephenson and Malanowski, 1987Based on data from 473. to 531. K.; AC
34.8337.AStephenson and Malanowski, 1987Based on data from 322. to 368. K. See also Ambrose, 1968.; AC
34.776 ± 0.006190.CCounsell, Hales, et al., 1968, 2ALS
32.0388.EBEvans and Tiley, 1966, 2Based on data from 373. to 530. K.; AC
35.7313.N/APatrick and Prosser, 1964Based on data from 298. to 358. K. See also Boublik, Fried, et al., 1984.; AC

Enthalpy of vaporization

ΔvapH = A exp(-βTr) (1 − Tr)β
    ΔvapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    Tr = reduced temperature (T / Tc)

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Temperature (K) A (kJ/mol) β Tc (K) Reference Comment
321. to 359.54.240.2911532.Majer and Svoboda, 1985 

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
321.88 to 367.54.160861253.674-57.179Ambrose, 1968, 2Coefficents calculated by NIST from author's data.
373.36 to 529.534.63631635.174-3.684Evans and Tiley, 1966, 3Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
10.883225.67Paukov and Lavrent'eva, 1969DH
10.853225.83Counsell, Hales, et al., 1968DH
10.88225.7Acree, 1991AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
48.22225.67Paukov and Lavrent'eva, 1969DH
48.06225.83Counsell, Hales, et al., 1968DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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

Fluorine anion + Benzene, pentafluoro- = (Fluorine anion • Benzene, pentafluoro-)

By formula: F- + C6HF5 = (F- • C6HF5)

Quantity Value Units Method Reference Comment
Δr122. ± 8.4kJ/molIMREDillow and Kebarle, 1988gas phase; Anchored to C6F6..F- in Hiraoka, Mizuse, et al., 1987; B,M
Quantity Value Units Method Reference Comment
Δr84.1J/mol*KN/ADillow and Kebarle, 1988gas phase; switching reaction,Thermochemical ladder(F-)C6F6, Entropy change calculated or estimated; Hiraoka, Mizuse, et al., 1987; M
Quantity Value Units Method Reference Comment
Δr86.6 ± 8.4kJ/molIMREDillow and Kebarle, 1988gas phase; Anchored to C6F6..F- in Hiraoka, Mizuse, et al., 1987; B

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
86.6423.PHPMSDillow and Kebarle, 1988gas phase; switching reaction,Thermochemical ladder(F-)C6F6, Entropy change calculated or estimated; Hiraoka, Mizuse, et al., 1987; M

C6F5- + Hydrogen cation = Benzene, pentafluoro-

By formula: C6F5- + H+ = C6HF5

Quantity Value Units Method Reference Comment
Δr1492. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Δr<1559.6 ± 1.3kJ/molG+TSHerd, Adams, et al., 1989gas phase; More acidic than HF, less than HCl; B
Δr1539. ± 21.kJ/molD-EACompton and Reinhardt, 1982gas phase; From perfluorobenzene; B
Quantity Value Units Method Reference Comment
Δr1460. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Δr<1527.2kJ/molIMRBHerd, Adams, et al., 1989gas phase; More acidic than HF, less than HCl; B
Δr1507. ± 21.kJ/molH-TSCompton and Reinhardt, 1982gas phase; From perfluorobenzene; B

C6H6+ + Benzene, pentafluoro- = (C6H6+ • Benzene, pentafluoro-)

By formula: C6H6+ + C6HF5 = (C6H6+ • C6HF5)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Δr46.9kJ/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr110.J/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kJ/mol) T (K) Method Reference Comment
13.300.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Chromium ion (1+) + Benzene, pentafluoro- = (Chromium ion (1+) • Benzene, pentafluoro-)

By formula: Cr+ + C6HF5 = (Cr+ • C6HF5)

Quantity Value Units Method Reference Comment
Δr99.2kJ/molRAKRyzhov, 1999RCD

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, References, Notes

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

Gas Phase Spectrum

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IR spectrum
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Additional Data

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Owner NIST Standard Reference Data Program
Collection (C) 2018 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin NIST Mass Spectrometry Data Center
State gas
Instrument HP-GC/MS/IRD

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, UV/Visible spectrum, References, Notes

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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Mass spectrum
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Additional Data

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Due to licensing restrictions, this spectrum cannot be downloaded.

Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW-5591
NIST MS number 235500

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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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UVVis spectrum
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Additional Data

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Source Vorozhtsov, Barhash, et al., 1964
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 62
Instrument Spectrophotometer SF-16
Melting point -48
Boiling point 85

References

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

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

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]

Paukov and Lavrent'eva, 1969
Paukov, I.E.; Lavrent'eva, M.N., Thermodynamic properties of pentafluorobenzene over the range 12-300K, Zhur. Fiz. Khim., 1969, 43, 2938-2941. [all data]

Counsell, Hales, et al., 1968
Counsell, J.F.; Hales, J.L.; Martin, J.F., Thermodynamic properties of fluorine compounds. Part VI. The heat capacity and entropy of pentafluorobenzene, J. Chem. Soc. A, 1968, 2042-2044. [all data]

Paukov and Lavrent'eva, 1969, 2
Paukov, I.E.; Lavrent'eva, M.N., Thermodynamic properties of pentafluorobenzene over the range 12-300 K, Zh. Fiz. Khim., 1969, 43, 2938. [all data]

Counsell, Hales, et al., 1968, 2
Counsell, J.F.; Hales, J.L.; Martin, J.F., Thermodynamic properties of flourine compounds. Part VI. The heat capacity and entropy of pentafluorobenzene, J. Chem. Soc. A, 1968, 2042. [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]

Skripov and Muratov, 1977
Skripov, V.P.; Muratov, G.N., The surface tensions of liquids and their interpretation by the method of thermodynamic similarity., Russ. J. Phys. Chem. (Engl. Transl.), 1977, 51, 806-8. [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]

Ambrose and Sprake, 1971
Ambrose, D.; Sprake, C.H.S., Thermodynamic properties of fluorine compounds: x critical properties and vapour pressures of pentafluorobenzene, chloropentafluorobenzene, 2,3,4,5,6 -pentafluorotoluene, and pentafluorophenol, J. Chem. Soc. A, 1971, 1971, 1263. [all data]

Evans and Tiley, 1966
Evans, F.D.; Tiley, P.F., Vapour Pressures and Critical Constants of Hexafluoro, Pentafluoro-, Chloropentafrluoro-, and Bromopentafluoro-benzene, J. Chem. Soc. B, 1966, 1966, 134-6. [all data]

Invernizzi, 1982
Invernizzi, C., Termotecnica, 1982, 4, 78. [all data]

Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav, Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data, Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I . [all data]

Findlay, 1969
Findlay, T.J.V., Vapor pressures of fluorobenzenes from 5° to 50°C, J. Chem. Eng. Data, 1969, 14, 229. [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]

Ambrose, 1968
Ambrose, D., Thermodynamic properties of fluorine compounds. Part V. Vapour pressures of pentafluorobenzene, chloropentafluorobenzene, 2,3,4,5,6-pentafluorotoluene, and pentafluorophenol, J. Chem. Soc., A, 1968, 1381, https://doi.org/10.1039/j19680001381 . [all data]

Evans and Tiley, 1966, 2
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]

Ambrose, 1968, 2
Ambrose, D., Thermodynamic Properties of Fluorine Compounds. Part V. Vapour Pressures of Pentafluorobenzene, Chloropentafluorobenzene, 2,3,4,5,6-Pentafluorotoluene, and Pentafluorophenol, J. Chem. Soc. A:, 1968, 1381-1383, https://doi.org/10.1039/j19680001381 . [all data]

Evans and Tiley, 1966, 3
Evans, F.D.; Tiley, Vapour Pressures and Critical Constants of Hexafluoro-, Pentafluoro-, Chloropentafluoro-, and Bromopentafluoro-benzene, J. Chem. Soc. B:, 1966, 134-136, https://doi.org/10.1039/j29660000134 . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Dillow and Kebarle, 1988
Dillow, G.W.; Kebarle, P., Fluoride Affinities of Perfluorobenzenes C6F5X. Meisenheimer Complexes in the Gas Phase and Solution, J. Am. Chem. Soc., 1988, 110, 15, 4877, https://doi.org/10.1021/ja00223a001 . [all data]

Hiraoka, Mizuse, et al., 1987
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]

Buker, Nibbering, et al., 1997
Buker, H.H.; Nibbering, N.M.M.; Espinosa, D.; Mongin, F.; Schlosser, M., Additivity of substituent effects in the fluoroarene series: Equilibrium acidity in the gas phase and deprotonation rates in ethereal solution, Tetrahed. Lett., 1997, 38, 49, 8519-8522, https://doi.org/10.1016/S0040-4039(97)10303-3 . [all data]

Herd, Adams, et al., 1989
Herd, C.R.; Adams, N.G.; Smith, D., FALP Studies of Electron Attachment Reactions of C6F5Cl, C6F5Br, and C6F5I, Int. J. Mass Spectrom. Ion Proc., 1989, 87, 3, 331, https://doi.org/10.1016/0168-1176(89)80032-1 . [all data]

Compton and Reinhardt, 1982
Compton, R.N.; Reinhardt, P.W., Collisonal ionization between fast alkali atoms and hexafluorobenzene, Chem. Phys. Lett., 1982, 91, 268. [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]

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]

Vorozhtsov, Barhash, et al., 1964
Vorozhtsov, N.N.; Barhash, V.a.; Ivanova, N.G.; Anichkina, S.A.; Andrievskaya, O.I., Synthesis and reactions of pentaflluorophenyl- and heptafluoronaphthyl magnesiumchlorides, Dokl. Akad. Nauk SSSR, 1964, 159, 1, 125-128. [all data]


Notes

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