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Benzene, fluoro-

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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:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C6H5F+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.20 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)755.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity726.6kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.20PEFujisawa, Ohno, et al., 1986LBLHLM
9.20PEKimura, Katsumata, et al., 1981LLK
9.22PESell, Mintz, et al., 1978LLK
9.17PEBehan, Johnstone, et al., 1976LLK
9.75EIBaldwin, Loudon, et al., 1976LLK
9.11PEDebies and Rabalais, 1973LLK
9.20SSmith and Raymonda, 1971LLK
9.20SGilbert and Sandorfy, 1971LLK
9.182PIMomigny, Goffart, et al., 1968RDSH
9.21 ± 0.04PEClark and Frost, 1967RDSH
9.20 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
9.20PIBralsford, Harris, et al., 1960RDSH
9.200 ± 0.005SHammond, Price, et al., 1950RDSH
9.22PESell and Kupperman, 1978Vertical value; LLK
9.37PEKobayashi, 1978Vertical value; LLK
9.19PEStreets and Ceasar, 1973Vertical value; LLK
9.35 ± 0.03PEKlessinger, 1972Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3F+16.13 ± 0.13C4H2PIPECONishimura, Meisels, et al., 1991LL
C3H2F+15.13 ± 0.13C3H3PIPECONishimura, Meisels, et al., 1991LL
C3H2F+15.8 ± 0.1?EIMomigny, 1959RDSH
C3H3+15.13 ± 0.13C3H2FPIPECONishimura, Meisels, et al., 1991LL
C3H3+14.3 ± 0.1?EIMomigny, 1959RDSH
C4H2+15.13 ± 0.13C2H3FPIPECONishimura, Meisels, et al., 1991LL
C4H3F+13.14 ± 0.05C2H2PIPECONishimura, Meisels, et al., 1991LL
C4H3F+14.73C2H2EIHowe and Williams, 1969RDSH
C4H4+15.90 ± 0.09C2HFPIPECONishimura, Meisels, et al., 1991LL
C4H4+17.0 ± 0.1?EIMomigny, 1959RDSH
C5H2F+16.13 ± 0.13CH3PIPECONishimura, Meisels, et al., 1991LL
C5H3+15.13 ± 0.13CH2FPIPECONishimura, Meisels, et al., 1991LL
C6H4+15.4 ± 0.1HFEIMomigny, 1959RDSH
C6H4F+14.1HEIYeo and Williams, 1970RDSH
C6H5+13.10 ± 0.05FPIPECONishimura, Meisels, et al., 1991LL
C6H5+14.5 ± 0.1FEIMajer and Patrick, 1962RDSH

De-protonation reactions

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Deltar1618. ± 8.8kJ/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Deltar1620. ± 8.8kJ/molG+TSAndrade and Riveros, 1996gas phase; B
Deltar1620. ± 10.kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar1620. ± 10.kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Deltar1620. ± 23.kJ/molG+TSBriscese and Riveros, 1975gas phase; B
Quantity Value Units Method Reference Comment
Deltar1584. ± 8.4kJ/molIMREBuker, Nibbering, et al., 1997gas phase; B
Deltar1586. ± 8.4kJ/molIMREAndrade and Riveros, 1996gas phase; B
Deltar1585. ± 8.4kJ/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
Deltar1586. ± 11.kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Deltar1586. ± 22.kJ/molIMRBBriscese and Riveros, 1975gas phase; B

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Deltar1671.9 ± 3.8kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Deltar1639. ± 4.2kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
Deltar1654. ± 8.4kJ/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
Deltar1619. ± 8.8kJ/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

References

Go To: Top, 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.

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]

Fujisawa, Ohno, et al., 1986
Fujisawa, S.; Ohno, K.; Masuda, S.; Harada, Y., Penning ionization electron spectroscopy of monohalogenobenzenes: C6H5F, C6H5Cl, C6H5Br, and C6H5I, J. Am. Chem. Soc., 1986, 108, 6505. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

Sell, Mintz, et al., 1978
Sell, J.A.; Mintz, D.M.; Kupperman, A., Photoelectron angular distributions of carbon-carbon «pi» electrons in ethylene, benzene, and their fluorinated derivatives, Chem. Phys. Lett., 1978, 58, 601. [all data]

Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W., An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes, Org. Mass Spectrom., 1976, 11, 207. [all data]

Baldwin, Loudon, et al., 1976
Baldwin, M.A.; Loudon, A.G.; Maccoll, A.; Webb, K.S., The nature and fragmentation pathways of the molecular ions of some arylureas, arylthioureas, acetanilides, thioacetanilides and related compounds, Org. Mass Spectrom., 1976, 11, 1181. [all data]

Debies and Rabalais, 1973
Debies, T.P.; Rabalais, J.W., Photoelectron spectra of substituted benzenes. II. Seven valence electron substituents, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 355. [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]

Gilbert and Sandorfy, 1971
Gilbert, R.; Sandorfy, C., The vacuum-ultraviolet spectrum of fluorobenzene, Chem. Phys. Lett., 1971, 9, 121. [all data]

Momigny, Goffart, et al., 1968
Momigny, J.; Goffart, C.; D'Or, L., Photoionization studies by total ionization measurements. I. Benzene and its monohalogeno derivatives, Intern. J. Mass Spectrom. Ion Phys., 1968, 1, 53. [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]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]

Hammond, Price, et al., 1950
Hammond, V.J.; Price, W.C.; Teegan, J.P.; Walsh, A.D., The absorption spectra of some substituted benzenes and naphthalenes in the vacuum ultra-violet, Faraday Discuss. Chem. Soc., 1950, 9, 53. [all data]

Sell and Kupperman, 1978
Sell, J.A.; Kupperman, A., Angular distributions in the photoelectron spectra of benzene and its monohalogenated derivatives, Chem. Phys., 1978, 33, 367. [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]

Streets and Ceasar, 1973
Streets, D.G.; Ceasar, G.P., Inductive mesomeric effects on the «pi» orbitals of halobenzenes, Mol. Phys., 1973, 26, 1037. [all data]

Klessinger, 1972
Klessinger, M., Ionization potentials of substituted benzenes, Angew. Chem. Int. Ed. Engl., 1972, 11, 525. [all data]

Nishimura, Meisels, et al., 1991
Nishimura, T.; Meisels, G.; Niwa, Y., Fragmentation of energy-selected fluorobenzene ion, Bull. Chem. Soc. Jpn., 1991, 64, 2894. [all data]

Momigny, 1959
Momigny, J., Determination et discussion des potentials d'apparition d'ions fragmentaires dans le benzene et ses derives monohalogenes, Bull. Soc. Roy. Sci. Liege, 1959, 28, 251. [all data]

Howe and Williams, 1969
Howe, I.; Williams, D.H., Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes, J. Am. Chem. Soc., 1969, 91, 7137. [all data]

Yeo and Williams, 1970
Yeo, A.N.H.; Williams, D.H., Rearrangement in the molecular ions of halogenotoluenes prior to fragmentation in the mass spectrometer, Chem. Commun., 1970, 886. [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]

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]

Andrade and Riveros, 1996
Andrade, P.B.M.; Riveros, J.M., Relative Gas-phase Acidities of Fluoro- and Chlorobenzene, J. Mass Spectrom., 1996, 31, 7, 767, https://doi.org/10.1002/(SICI)1096-9888(199607)31:7<767::AID-JMS345>3.0.CO;2-Q . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method, J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105 . [all data]

Briscese and Riveros, 1975
Briscese, S.M.J.; Riveros, J.M., Gas phase nucleophilic reactions of aromatic systems, J. Am. Chem. Soc., 1975, 97, 230. [all data]


Notes

Go To: Top, Gas phase ion energetics data, References