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-192.6 ± 0.33kcal/molCcrCox, Gundry, et al., 1969 

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
Δr29.2 ± 2.0kcal/molIMREDillow and Kebarle, 1988gas phase; Anchored to C6F6..F- in Hiraoka, Mizuse, et al., 1987; B,M
Quantity Value Units Method Reference Comment
Δr20.1cal/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
Δr20.7 ± 2.0kcal/molIMREDillow and Kebarle, 1988gas phase; Anchored to C6F6..F- in Hiraoka, Mizuse, et al., 1987; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
20.7423.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
Δr356.7 ± 2.1kcal/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Δr<372.75 ± 0.30kcal/molG+TSHerd, Adams, et al., 1989gas phase; More acidic than HF, less than HCl; B
Δr367.8 ± 5.0kcal/molD-EACompton and Reinhardt, 1982gas phase; From perfluorobenzene; B
Quantity Value Units Method Reference Comment
Δr349.0 ± 2.0kcal/molIMREBuker, Nibbering, et al., 1997gas phase; B
Δr<365.00kcal/molIMRBHerd, Adams, et al., 1989gas phase; More acidic than HF, less than HCl; B
Δr360.1 ± 5.1kcal/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
Δr11.2kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr27.cal/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
3.1300.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
Δr23.7kcal/molRAKRyzhov, 1999RCD

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Ion clustering data, Gas Chromatography, References, Notes

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)165.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity158.4kcal/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
Δr356.7 ± 2.1kcal/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Δr<372.75 ± 0.30kcal/molG+TSHerd, Adams, et al., 1989gas phase; More acidic than HF, less than HCl; B
Δr367.8 ± 5.0kcal/molD-EACompton and Reinhardt, 1982gas phase; From perfluorobenzene; B
Quantity Value Units Method Reference Comment
Δr349.0 ± 2.0kcal/molIMREBuker, Nibbering, et al., 1997gas phase; B
Δr<365.00kcal/molIMRBHerd, Adams, et al., 1989gas phase; More acidic than HF, less than HCl; B
Δr360.1 ± 5.1kcal/molH-TSCompton and Reinhardt, 1982gas phase; From perfluorobenzene; B

Ion clustering data

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References, Notes

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
Δr11.2kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Δr27.cal/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
3.1300.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
Δr23.7kcal/molRAKRyzhov, 1999RCD

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

By formula: F- + C6HF5 = (F- • C6HF5)

Quantity Value Units Method Reference Comment
Δr29.2 ± 2.0kcal/molIMREDillow and Kebarle, 1988gas phase; Anchored to C6F6..F- in Hiraoka, Mizuse, et al., 1987; B,M
Quantity Value Units Method Reference Comment
Δr20.1cal/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
Δr20.7 ± 2.0kcal/molIMREDillow and Kebarle, 1988gas phase; Anchored to C6F6..F- in Hiraoka, Mizuse, et al., 1987; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
20.7423.PHPMSDillow and Kebarle, 1988gas phase; switching reaction,Thermochemical ladder(F-)C6F6, Entropy change calculated or estimated; Hiraoka, Mizuse, et al., 1987; M

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

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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, 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]

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]

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]

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, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References