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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Gas phase ion energetics data
Go To: Top, Mass spectrum (electron ionization), 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:
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
Mass spectrum (electron ionization)
Go To: Top, 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 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-3049 |
NIST MS number | 231244 |
Gas Chromatography
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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | C78, Branched paraffin | 130. | 546.8 | Dallos, Sisak, et al., 2000 | He; Column length: 3.3 m |
Packed | C78, Branched paraffin | 130. | 548.7 | Reddy, Dutoit, et al., 1992 | Chromosorb G HP; Column length: 3.3 m |
Packed | Squalane | 50. | 576. | Müller, Dietrich, et al., 1983 | |
Packed | Squalane | 100. | 571. | Vernon and Edwards, 1975 | N2, DCMS-treated Celite; Column length: 1. m |
Packed | Apiezon L | 100. | 569. | Brown, Chapman, et al., 1968 | N2, DCMS-treated Chromosorb W; Column length: 2.3 m |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 600. | Peng, Ding, et al., 1988 | He, Supelcoport and Chromosorb, 40. C @ 4. min, 10. K/min, 250. C @ 60. min; Column length: 3.05 m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 592. | Zenkevich, 2008 | 25. m/0.25 mm/0.20 μm, Nitrogen, 60. C @ 0. min, 6. K/min, 240. C @ 0. min |
Capillary | OV-101 | 609. | Zenkevich, Eliseenkov, et al., 2006 | Nitrogen, 6. K/min, 240. C @ 10. min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 60. C |
References
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
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]
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]
Dallos, Sisak, et al., 2000
Dallos, A.; Sisak, A.; Kulcsár, Z.; Kováts, E.,
Pair-wise interactions by gas chromatography VII. Interaction free enthalpies of solutes with secondary alcohol groups,
J. Chromatogr. A, 2000, 904, 2, 211-242, https://doi.org/10.1016/S0021-9673(00)00908-0
. [all data]
Reddy, Dutoit, et al., 1992
Reddy, K.S.; Dutoit, J.-Cl.; Kovats, E. sz.,
Pair-wise interactions by gas chromatography. I. Interaction free enthalpies of solutes with non-associated primary alcohol groups,
J. Chromatogr., 1992, 609, 1-2, 229-259, https://doi.org/10.1016/0021-9673(92)80167-S
. [all data]
Müller, Dietrich, et al., 1983
Müller, U.; Dietrich, P.; Prescher, D.,
Gaschromatographische Untersuchungen an Perfluor-Carbonverbindungen. II. Zur Gaschromatographischen Trennung von Gemischen Längerkettiger Perfluoralkane und Perfluoralkene,
J. Chromatogr., 1983, 259, 243-254, https://doi.org/10.1016/S0021-9673(01)88005-5
. [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]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
. [all data]
Zenkevich, 2008
Zenkevich, I.G.,
Experimental data, Personal communication, 2008. [all data]
Zenkevich, Eliseenkov, et al., 2006
Zenkevich, I.G.; Eliseenkov, E.V.; Kasatochkin, A.N.,
Application of Retention Indices in GC-MS Identification of Halogenated Organic Compounds,
Mass Spectromery (Rus.), 2006, 3, 2, 131-140. [all data]
Notes
Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity IE (evaluated) Recommended ionization energy - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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