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Ethylbenzene

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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
MM - Michael M. Meot-Ner (Mautner)
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

View reactions leading to C8H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.77 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)788.0kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity760.3kJ/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
789.9Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
760.2Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.77PEHowell, Goncalves, et al., 1984LBLHLM
8.61PEKlasinc, Kovac, et al., 1983LBLHLM
8.65 ± 0.10EISelim and Helal, 1982LBLHLM
8.76EIMcLoughlin, Morrison, et al., 1979LLK
8.768 ± 0.008EQLias and Ausloos, 1978LLK
8.75 ± 0.05PIAkopyan and Vilesov, 1966RDSH
8.76 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
8.77 ± 0.01SHammond, Price, et al., 1950RDSH
8.77PEHowell, Goncalves, et al., 1984Vertical value; LBLHLM
8.73PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
9.38PEDeshmukh, Dutta, et al., 1982Vertical value; LBLHLM

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C5H5+16.2 ± 0.2C2H2+CH3EITajima and Tsuchiya, 1973LLK
C6H6+11.0 ± 0.1C2H4?PIAkopyan and Vilesov, 1966RDSH
C7H7+9.9 ± 0.1CH3TRPILifshitz and Malinovich, 1984LBLHLM
C7H7+10.15 ± 0.10CH3EISelim and Helal, 1982LBLHLM
C7H7+10.06CH3EIMcLoughlin, Morrison, et al., 1979LLK
C7H7+10.9 ± 0.1CH3PIAkopyan and Vilesov, 1966RDSH
C8H9+10.60HEIMcLoughlin, Morrison, et al., 1979LLK
C8H9+12.1 ± 0.1HPIAkopyan and Vilesov, 1966RDSH
C8H9+11.4 ± 0.1HEIMeyer, Haynes, et al., 1965RDSH

De-protonation reactions

C8H9- + Hydrogen cation = Ethylbenzene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar1699. ± 19.kJ/molCIDTGraul and Squires, 1990gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B
Quantity Value Units Method Reference Comment
Deltar1664. ± 20.kJ/molH-TSGraul and Squires, 1990gas phase; From decarboxylation threshold. Stable form probably the spiro[2.5]octadienide Maas and van Keelen, 1989; B

C8H9- + Hydrogen cation = Ethylbenzene

By formula: C8H9- + H+ = C8H10

Quantity Value Units Method Reference Comment
Deltar1589. ± 8.8kJ/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1562. ± 8.4kJ/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; 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]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Howell, Goncalves, et al., 1984
Howell, J.O.; Goncalves, J.M.; Amatore, C.; Klasinc, L.; Wightman, R.M.; Kochi, J.K., Electron transfer from aromatic hydrocarbons and their «pi»-complexes with metals. Comparison of the standard oxidation potentials and vertical ionization potentials, J. Am. Chem. Soc., 1984, 106, 3968. [all data]

Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H., Photoelectron spectra of acenes. Electronic structure and substituent effects, Pure Appl. Chem., 1983, 55, 289. [all data]

Selim and Helal, 1982
Selim, E.T.M.; Helal, A.I., The study of C1-C3 monosubstituted alkyl benzenes by the inverse convolution of first differential ionization efficiency curves, Org. Mass Spectrom., 1982, 17, 539. [all data]

McLoughlin, Morrison, et al., 1979
McLoughlin, R.G.; Morrison, J.D.; Traeger, J.C., Photoionization of the C-1 - C-4 monosubstituted alkyl benzenes: Thermochemistry of [C7H7]+ and [C8H9]+ formation, Org. Mass Spectrom., 1979, 14, 104. [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]

Akopyan and Vilesov, 1966
Akopyan, M.E.; Vilesov, F.I., A mass-spectrometric study of the photo-ionisation of benzene derivatives at wavelengths up to 885 A, Zh. Fiz. Khim., 1966, 40, 125, In original 63. [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]

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]

Deshmukh, Dutta, et al., 1982
Deshmukh, P.; Dutta, T.K.; Hwang, J.L.-S.; Housecroft, C.E.; Fehlner, T.P., Photoelectron spectroscopic measurements of the relative charge on carbyne fragments bound to polynuclear cobalt carbonyl clusters, J. Am. Chem. Soc., 1982, 104, 1740. [all data]

Tajima and Tsuchiya, 1973
Tajima, S.; Tsuchiya, T., Energetics consideration of C5H5+ ions produced from various precursors by electron impact, Bull. Chem. Soc. Jpn., 1973, 46, 3291. [all data]

Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y., Time resolved photoionization mass spectrometry in the millisecond range, Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]

Meyer, Haynes, et al., 1965
Meyer, F.; Haynes, P.; McLean, S.; Harrison, A.G., An electron impact study of some C8H10 isomers, Can. J. Chem., 1965, 43, 211. [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Maas and van Keelen, 1989
Maas, W.P.M.; van Keelen, P.A., On the Generation and Characterization of the Spiro[2,5]Octadienyl Anion in the Gas Phase, Org. Mass Spectrom., 1989, 24, 8, 546, https://doi.org/10.1002/oms.1210240807 . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]


Notes

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