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 

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, 1969Uncertainty assigned by TRC = 0.02 K; TRC
Ttriple225.83KN/ACounsell, Hales, et al., 1968Uncertainty 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., 1968ALS
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, 1969, 2DH
10.853225.83Counsell, Hales, et al., 1968, 2DH
10.88225.7Acree, 1991AC

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
48.22225.67Paukov and Lavrent'eva, 1969, 2DH
48.06225.83Counsell, Hales, et al., 1968, 2DH

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:


Gas phase ion energetics 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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Quantity Value Units Method Reference Comment
IE (evaluated)9.63eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)690.4kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity662.7kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
<0.434 ± 0.087IMRBDillow and Kebarle, 1989Observed only at 303K and below; B
0.730 ± 0.080ECDWentworth, Limero, et al., 1987B

Ionization energy determinations

IE (eV) Method Reference Comment
9.73PESell, Mintz, et al., 1978LLK
9.631 ± 0.004EQLias and Ausloos, 1978LLK
9.82SSmith and Raymonda, 1971LLK
9.84PIBralsford, Harris, et al., 1960RDSH
9.90PETrudell and Price, 1979Vertical value; LLK
9.64PEStreets and Ceasar, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6HF4+16.5 ± 0.1FEIMajer and Patrick, 1962RDSH

De-protonation reactions

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

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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
B - John E. Bartmess

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

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

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

IR 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: 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 .


Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR 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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedSqualane100.589.Vernon and Edwards, 1975N2, DCMS-treated Celite; Column length: 1. m
PackedApiezon L100.594.Brown, Chapman, et al., 1968N2, DCMS-treated Chromosorb W; Column length: 2.3 m

References

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, 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 12-300 K, Zh. Fiz. Khim., 1969, 43, 2938. [all data]

Counsell, Hales, et al., 1968
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]

Paukov and Lavrent'eva, 1969, 2
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, 2
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]

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Dillow and Kebarle, 1989
Dillow, G.W.; Kebarle, P., Substituent Effects on the Electron Affinities of Perfluorobenzenes C6F5X, J. Am. Chem. Soc., 1989, 111, 15, 5592, https://doi.org/10.1021/ja00197a014 . [all data]

Wentworth, Limero, et al., 1987
Wentworth, W.E.; Limero, T.; Chen, E.C.M., Electron Affinities of Hexafluorobenzene and Pentafluorobenzene, J. Phys. Chem., 1987, 91, 1, 241, https://doi.org/10.1021/j100285a051 . [all data]

Sell, Mintz, et al., 1978
Sell, J.A.; Mintz, D.M.; Kupperman, A., Photoelectron angular distributions of carbon-carbon π electrons in ethylene, benzene, and their fluorinated derivatives, Chem. Phys. Lett., 1978, 58, 601. [all data]

Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J., eIonization energies of organic compounds by equilibrium measurements, J. Am. Chem. Soc., 1978, 100, 6027. [all data]

Smith and Raymonda, 1971
Smith, D.R.; Raymonda, J.W., Rydberg states in fluorinated benzenes; hexa-, penta-, and mono- fluorobenzene, Chem. Phys. Lett., 1971, 12, 269. [all data]

Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C., The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proc. Roy. Soc. (London), 1960, A258, 459. [all data]

Trudell and Price, 1979
Trudell, B.C.; Price, S.J.W., The ultraviolet photoelectron spectra of C6F5X compounds, X=(F, Cl, Br, I, H, CH3), Can. J. Chem., 1979, 57, 2256. [all data]

Streets and Ceasar, 1973
Streets, D.G.; Ceasar, G.P., Inductive mesomeric effects on the π orbitals of halobenzenes, Mol. Phys., 1973, 26, 1037. [all data]

Majer and Patrick, 1962
Majer, J.R.; Patrick, C.R., Electron impact on some halogenated aromatic compounds, J. Chem. Soc. Faraday Trans., 1962, 58, 17. [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]

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]

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]


Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Gas Chromatography, References