Benzene, hexafluoro-

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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:
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 ± 0.04eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)154.9kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity149.2kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.530 ± 0.050KineMiller, Van Doren, et al., 2004B
0.52 ± 0.11IMREDillow and Kebarle, 1989ΔGea(423 K) = -14.9±1.0 kcal/mol at 423 K, assumed entropy = 3.5 eu; B
0.70 ± 0.10LPESEustis, Wang, et al., 2007Vertical Detachment Energy: 1.55±0.02 eV; B
0.477006KineChristophorou and Datkos, 1995B
0.80 ± 0.10LPESNakajima, Taguwa, et al., 1993Vertical Detachment Energy: 1.56±0.03 eV; B
0.83 ± 0.20TDAsChen, Wiley, et al., 1994Claim that Kebarle and Chowdhury, 1987 involves an excited state; B
0.860 ± 0.030ECDWentworth, Limero, et al., 1987B
1.80 ± 0.30EndoLifshitz, Tiernan, et al., 1973B
1.200 ± 0.069SIPage and Goode, 1969The Magnetron method, lacking mass analysis, is not considered reliable.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.8PEMaier and Thommen, 1981LLK
9.906PEBieri, Asbrink, et al., 1981LLK
9.90 ± 0.05PEBastide, Hall, et al., 1979LLK
9.91PESell, Mintz, et al., 1978LLK
10.2 ± 0.1EIPraet, Hubin-Franskin, et al., 1977LLK
9.93PEBrundle, Robin, et al., 1972LLK
9.90 ± 0.01SSmith and Raymonda, 1971LLK
9.88 ± 0.05PEClark and Frost, 1967RDSH
9.97PIBralsford, Harris, et al., 1960RDSH
10.2PEBieri, Asbrink, et al., 1981Vertical value; LLK
10.14PETrudell and Price, 1979Vertical value; LLK
10.09PEKobayashi, 1978Vertical value; LLK
10.09PEKobayashi and Nagakura, 1975Vertical value; LLK
9.90PEStreets and Ceasar, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CF+18.3 ± 0.1?EIPraet, Hubin-Franskin, et al., 1977LLK
CF+17.3 ± 0.3?EIDibeler, Reese, et al., 1957RDSH
CF3+25.2 ± 0.4CF+C3+CF2EIPraet, Hubin-Franskin, et al., 1977LLK
CF3+15.3 ± 0.5?EIPraet, Hubin-Franskin, et al., 1977LLK
CF3+21.3 ± 0.4CF+C4F2EIPraet, Hubin-Franskin, et al., 1977LLK
CF3+17.1?EIDibeler, Reese, et al., 1957RDSH
C3F+22. ± 1.?EIDibeler, Reese, et al., 1957RDSH
C3F2+15.8 ± 0.1?EIPraet, Hubin-Franskin, et al., 1977LLK
C3F2+18.9 ± 0.5?EIDibeler, Reese, et al., 1957RDSH
C3F3+16.5 ± 0.4C3F3EIPraet, Hubin-Franskin, et al., 1977LLK
C3F3+21. ± 0.4CF+C2F2EIPraet, Hubin-Franskin, et al., 1977LLK
C3F3+17.1 ± 0.2C3F3EIPraet, Hubin-Franskin, et al., 1977LLK
C3F3+16.8 ± 0.3?EIDibeler, Reese, et al., 1957RDSH
C4F2+19.8 ± 0.5?EIPraet, Hubin-Franskin, et al., 1977LLK
C4F2+18. ± 1.?EIDibeler, Reese, et al., 1957RDSH
C5F+29.0 ± 0.5?EIDibeler, Reese, et al., 1957RDSH
C5F2+20.7 ± 0.1?EIPraet, Hubin-Franskin, et al., 1977LLK
C5F2+24.8 ± 0.4F2+CF2EIPraet, Hubin-Franskin, et al., 1977LLK
C5F2+24.8 ± 0.4F+CF3EIPraet, Hubin-Franskin, et al., 1977LLK
C5F2+22. ± 1.?EIDibeler, Reese, et al., 1957RDSH
C5F3+15.85 ± 0.01CF3ENDAdams, Smith, et al., 1985LBLHLM
C5F3+16.1 ± 0.4CF3EIPraet, Hubin-Franskin, et al., 1977LLK
C5F3+15.8 ± 0.1?EIPraet, Hubin-Franskin, et al., 1977LLK
C5F3+18.8 ± 0.4F+CF2EIPraet, Hubin-Franskin, et al., 1977LLK
C5F3+15.8 ± 0.2?EIDibeler, Reese, et al., 1957RDSH
C5F4+16.4 ± 0.2CF2EIPraet, Hubin-Franskin, et al., 1977LLK
C5F4+16.3 ± 0.4CF2EIPraet, Hubin-Franskin, et al., 1977LLK
C5F4+16.1 ± 0.3?EIDibeler, Reese, et al., 1957RDSH
C5F5+16.4 ± 0.2?EIPraet, Hubin-Franskin, et al., 1977LLK
C5F5+17.2 ± 0.2CFEIDibeler, Reese, et al., 1957RDSH
C6F5+17.2 ± 0.2FEIPraet, Hubin-Franskin, et al., 1977LLK
C6F5+16.86 ± 0.05FEIPrice and Sapiano, 1974LLK
C6F5+16.9 ± 0.1FEIMajer and Patrick, 1962RDSH
F+29.2 ± 0.5?EIDibeler, Reese, et al., 1957RDSH

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

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Column type Active phase Temperature (C) I Reference Comment
PackedC78, Branched paraffin130.546.8Dallos, Sisak, et al., 2000He; Column length: 3.3 m
PackedC78, Branched paraffin130.548.7Reddy, Dutoit, et al., 1992Chromosorb G HP; Column length: 3.3 m
PackedSqualane50.576.Müller, Dietrich, et al., 1983 
PackedSqualane100.571.Vernon and Edwards, 1975N2, DCMS-treated Celite; Column length: 1. m
PackedApiezon L100.569.Brown, Chapman, et al., 1968N2, DCMS-treated Chromosorb W; Column length: 2.3 m

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type Active phase I Reference Comment
PackedSE-30600.Peng, Ding, et al., 1988He, 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

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Column type Active phase I Reference Comment
CapillaryOV-101592.Zenkevich, 200825. m/0.25 mm/0.20 μm, Nitrogen, 60. C @ 0. min, 6. K/min, 240. C @ 0. min
CapillaryOV-101609.Zenkevich, Eliseenkov, et al., 2006Nitrogen, 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, 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

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