Benzene, pentafluoro-

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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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:
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

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), 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)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

Mass spectrum (electron ionization)

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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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Additional Data

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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

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References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Notes

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

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]


Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), References