Benzene, hexafluoro-
- Formula: C6F6
- Molecular weight: 186.0546
- IUPAC Standard InChIKey: ZQBFAOFFOQMSGJ-UHFFFAOYSA-N
- 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
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Reaction thermochemistry data
Go To: Top, 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 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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 70.3 ± 4.2 | kJ/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B,M |
ΔrH° | 64.9 ± 4.2 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 94.1 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
ΔrS° | 113. | J/mol*K | PHPMS | Chowdhury and Kebarle, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 37. ± 6.7 | kJ/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B |
ΔrG° | 36. ± 6.7 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1987 | gas phase; B |
By formula: C6H6+ + C6F6 = (C6H6+ • C6F6)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50.6 | kJ/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
17. | 300. | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
By formula: C6H7N+ + C6F6 = (C6H7N+ • C6F6)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 47.3 | kJ/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | N/A | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 15. | kJ/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; Entropy change calculated or estimated; M |
By formula: C6F6- + C6F6 = (C6F6- • C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 39. ± 19. | kJ/mol | N/A | Nakajima, Taguwa, et al., 1993 | gas phase; Vertical Detachment Energy: 1.760±0.040 eV; B |
ΔrH° | 43.5 ± 4.2 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1990 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 111. | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1990 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 10. ± 8.4 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1990 | gas phase; B |
By formula: F- + C6F6 = (F- • C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 115. ± 4.2 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1987, 2 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 99.2 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 85.4 ± 6.7 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1987, 2 | gas phase; B |
By formula: I- + C6F6 = (I- • C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 46.0 ± 4.2 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 72.4 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 24. ± 6.7 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1987 | gas phase; B |
By formula: Br- + C6F6 = (Br- • C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 58.2 ± 4.2 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1987 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 81.2 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 34. ± 6.7 | kJ/mol | TDAs | Hiraoka, Mizuse, et al., 1987 | gas phase; B |
By formula: C6F6+ + C6F6 = (C6F6+ • C6F6)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 30. | kJ/mol | PHPMS | Hiraoka, Mizuse, et al., 1990 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 83.7 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1990 | gas phase; M |
By formula: (Cl- • C6F6) + C6F6 = (Cl- • 2C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 57.7 | kJ/mol | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
By formula: (I- • C6F6) + C6F6 = (I- • 2C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 43.5 | kJ/mol | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 90.4 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
By formula: (Br- • C6F6) + C6F6 = (Br- • 2C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 51.0 | kJ/mol | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 102. | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
By formula: (F- • C6F6) + C6F6 = (F- • 2C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 31. | kJ/mol | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 52.7 | J/mol*K | PHPMS | Hiraoka, Mizuse, et al., 1987 | gas phase; M |
By formula: Au- + C6F6 = C6AuF6-
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 100. ± 17. | kJ/mol | N/A | Ho and Dunbar, 1999 | gas phase; B |
By formula: Cr+ + C6F6 = (Cr+ • C6F6)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 79.1 | kJ/mol | RAK | Ryzhov, 1999 | RCD |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
B - John E. Bartmess
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.90 ± 0.04 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 648.0 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 624.4 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.530 ± 0.050 | Kine | Miller, Van Doren, et al., 2004 | B |
0.52 ± 0.11 | IMRE | Dillow and Kebarle, 1989 | ΔGea(423 K) = -14.9±1.0 kcal/mol at 423 K, assumed entropy = 3.5 eu; B |
0.70 ± 0.10 | LPES | Eustis, Wang, et al., 2007 | Vertical Detachment Energy: 1.55±0.02 eV; B |
0.477006 | Kine | Christophorou and Datkos, 1995 | B |
0.80 ± 0.10 | LPES | Nakajima, Taguwa, et al., 1993 | Vertical Detachment Energy: 1.56±0.03 eV; B |
0.83 ± 0.20 | TDAs | Chen, Wiley, et al., 1994 | Claim that Kebarle and Chowdhury, 1987 involves an excited state; B |
0.860 ± 0.030 | ECD | Wentworth, Limero, et al., 1987 | B |
1.80 ± 0.30 | Endo | Lifshitz, Tiernan, et al., 1973 | B |
1.200 ± 0.069 | SI | Page and Goode, 1969 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.8 | PE | Maier and Thommen, 1981 | LLK |
9.906 | PE | Bieri, Asbrink, et al., 1981 | LLK |
9.90 ± 0.05 | PE | Bastide, Hall, et al., 1979 | LLK |
9.91 | PE | Sell, Mintz, et al., 1978 | LLK |
10.2 ± 0.1 | EI | Praet, Hubin-Franskin, et al., 1977 | LLK |
9.93 | PE | Brundle, Robin, et al., 1972 | LLK |
9.90 ± 0.01 | S | Smith and Raymonda, 1971 | LLK |
9.88 ± 0.05 | PE | Clark and Frost, 1967 | RDSH |
9.97 | PI | Bralsford, Harris, et al., 1960 | RDSH |
10.2 | PE | Bieri, Asbrink, et al., 1981 | Vertical value; LLK |
10.14 | PE | Trudell and Price, 1979 | Vertical value; LLK |
10.09 | PE | Kobayashi, 1978 | Vertical value; LLK |
10.09 | PE | Kobayashi and Nagakura, 1975 | Vertical value; LLK |
9.90 | PE | Streets and Ceasar, 1973 | Vertical value; LLK |
Appearance energy determinations
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Chowdhury and Kebarle, 1986
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]
Hiraoka, Mizuse, et al., 1987
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]
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]
Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S.,
Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems,
J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026
. [all data]
Nakajima, Taguwa, et al., 1993
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]
Hiraoka, Mizuse, et al., 1990
Hiraoka, K.; Mizuse, S.; Yamabe, S.,
Stabilities and Structures of C6F6-(C6F6) and C6F6+(C6F6),
J. Phys. Chem., 1990, 94, 9, 3689, https://doi.org/10.1021/j100372a061
. [all data]
Hiraoka, Mizuse, et al., 1987, 2
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]
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]
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]
Miller, Van Doren, et al., 2004
Miller, T.M.; Van Doren, J.M.; Viggiano, A.A.,
Electron attachment and detachment: C6F6,
Int. J. Mass Spectrom., 2004, 233, 1-3, 67-73, https://doi.org/10.1016/j.ijms.2003.11.014
. [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]
Eustis, Wang, et al., 2007
Eustis, S.N.; Wang, D.; Bowen, K.H.; Patwari, G.N.,
Photoelectron spectroscopy of hydrated hexafluorobenzene anions,
J. Chem. Phys., 2007, 127, 11, 114312, https://doi.org/10.1063/1.2768349
. [all data]
Christophorou and Datkos, 1995
Christophorou, L.G.; Datkos, P.G.,
Effect of Temperature on the Formation and Autodestruction of Parent Anions,
Int. J. Mass Spectrom. Ion Proc., 1995, 149/150, 59, https://doi.org/10.1016/0168-1176(95)04229-E
. [all data]
Chen, Wiley, et al., 1994
Chen, E.C.M.; Wiley, J.R.; Batten, C.F.; Wentworth, W.E.,
Determination of the Electron Affinities of Molecules Using Negative Ion Mass Spectrometry,
J. Phys. Chem., 1994, 98, 1, 88, https://doi.org/10.1021/j100052a016
. [all data]
Kebarle and Chowdhury, 1987
Kebarle, P.; Chowdhury, S.,
Electron affinities and electron transfer reactions,
Chem. Rev., 1987, 87, 513. [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]
Lifshitz, Tiernan, et al., 1973
Lifshitz, C.; Tiernan, T.O.; Hughes, B.M.,
Electron affinities from endothermic negative-ion charge transfer reactions. IV. SF6, selected fluorocarbons, and other polyatomic molecules,
J. Chem. Phys., 1973, 59, 3182. [all data]
Page and Goode, 1969
Page, F.M.; Goode, G.C.,
Negative Ions and the Magnetron., Wiley, NY, 1969. [all data]
Maier and Thommen, 1981
Maier, J.P.; Thommen, F.,
Fluorescence quantum yields and lifetimes of fluorobenzene cations in selected levels of their B and C states determined by photoelectron-photoion coincidence spectroscopy,
Chem. Phys., 1981, 57, 319. [all data]
Bieri, Asbrink, et al., 1981
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4 nm He(II) photoelectron spectra of organic molecules. Part IV. Fluoro-compounds (C,H,F),
J. Electron Spectrosc. Relat. Phenom., 1981, 23, 281. [all data]
Bastide, Hall, et al., 1979
Bastide, J.; Hall, D.; Heilbronner, E.; Maier, J.P.,
He(Iα) photoelectron spectra of some higher aromatic perfluoro compounds,
J. Electron Spectrosc. Relat. Phenom., 1979, 16, 205. [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]
Praet, Hubin-Franskin, et al., 1977
Praet, M-Th.; Hubin-Franskin, M.J.; Delwiche, J.P.; Schoos, R.,
Ionization and dissociation of C6F6 isomers under electron impact,
Org. Mass Spectrom., 1977, 12, 297. [all data]
Brundle, Robin, et al., 1972
Brundle, C.R.; Robin, M.B.; Kuebler, N.A.,
Perfluoro effect in photoelectron spectroscopy. II. Aromatic molecules,
J. Am. Chem. Soc., 1972, 94, 1466. [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]
Clark and Frost, 1967
Clark, I.D.; Frost, D.C.,
A study of the energy levels in benzene and some fluorobenzenes by photoelectron spectroscopy,
J. Am. Chem. Soc., 1967, 89, 244. [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]
Kobayashi, 1978
Kobayashi, T.,
A simple general tendency in photoelectron angular distributions of some monosubstituted benzenes,
Phys. Lett., 1978, 69, 105. [all data]
Kobayashi and Nagakura, 1975
Kobayashi, T.; Nagakura, S.,
Angular distribution for the photoelectron spectra of benzene and hexafluorobenzene,
J. Electron Spectrosc. Relat. Phenom., 1975, 7, 187. [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]
Dibeler, Reese, et al., 1957
Dibeler, V.H.; Reese, R.M.; Mohler, F.L.,
Ionization and dissociation of hexafluorobenzene by electron impact,
J. Chem. Phys., 1957, 26, 304. [all data]
Adams, Smith, et al., 1985
Adams, N.G.; Smith, D.; Alge, E.,
Anomalous temperature dependence of the coefficient of electron attachment to hexafluorobenzene,
Chem. Phys. Lett., 1985, 116, 460. [all data]
Price and Sapiano, 1974
Price, S.J.W.; Sapiano, H.J.,
C6F5X bond dissociation energies: determination from appearance potential measurements and correlation with thermochemical data,
Can. J. Chem., 1974, 52, 4109. [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, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy T Temperature ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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