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Cyclohexene

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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

View reactions leading to C6H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)8.95 ± 0.01eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)187.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity179.7kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
8.94PEKimura, Katsumata, et al., 1981LLK
8.94 ± 0.02PEBieri, Burger, et al., 1977LLK
8.95EILossing and Traeger, 1975LLK
8.94 ± 0.01PERang, Paldoia, et al., 1974LLK
9.57 ± 0.05EIPraet, 1970RDSH
8.99EILewis and Hamill, 1970RDSH
8.92PEDemeo and Yencha, 1970RDSH
8.95 ± 0.01PIDemeo and El-Sayed, 1970RDSH
8.94PEBischof and Heilbronner, 1970RDSH
8.92 ± 0.02EIWinters and Collins, 1969RDSH
8.95 ± 0.01PIWatanabe, 1957RDSH
9.09PELambert, Xue, et al., 1986Vertical value; LBLHLM
9.12PEKobayashi, 1978Vertical value; LLK
9.12PEHentrich, Gunkel, et al., 1974Vertical value; LLK
9.12PEClary, Lewis, et al., 1974Vertical value; LLK
9.11PEAsmus and Klessinger, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.45 ± 0.18?EIWinters and Collins, 1969RDSH
C3H5+13.68 ± 0.05?EIPraet, 1970RDSH
C3H5+12.12 ± 0.12?EIWinters and Collins, 1969RDSH
C4H5+13.31 ± 0.15?EIWinters and Collins, 1969RDSH
C4H6+11.91 ± 0.05C2H4EIPraet, 1970RDSH
C4H6+10.67 ± 0.06?EIWinters and Collins, 1969RDSH
C5H5+13.57 ± 0.11?EIWinters and Collins, 1969RDSH
C5H7+8.95CH3EILossing and Traeger, 1975, 2LLK
C5H7+10.27CH3EILossing and Traeger, 1975LLK
C5H7+11.22 ± 0.05CH3EIPraet, 1970RDSH
C5H7+10.18 ± 0.12CH3EIWinters and Collins, 1969RDSH
C6H7+12.13 ± 0.10H2+HEIWinters and Collins, 1969RDSH
C6H9+11.8 ± 0.05HEIPraet, 1970RDSH
C6H9+10.62 ± 0.07HEIWinters and Collins, 1969RDSH

De-protonation reactions

C6H9- + Hydrogen cation = Cyclohexene

By formula: C6H9- + H+ = C6H10

Quantity Value Units Method Reference Comment
Deltar386.5 ± 5.1kcal/molG+TSLee and Squires, 1986gas phase; Between H2O, MeOH; B
Quantity Value Units Method Reference Comment
Deltar379.0 ± 5.0kcal/molIMRBLee and Squires, 1986gas phase; Between H2O, MeOH; 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]

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]

Bieri, Burger, et al., 1977
Bieri, G.; Burger, F.; Heilbronner, E.; Maier, J.P., Valence ionization enrgies of hydrocarbons, Helv. Chim. Acta, 1977, 60, 2213. [all data]

Lossing and Traeger, 1975
Lossing, F.P.; Traeger, J.C., Stabilization in cyclopentadienyl, cyclopentenyl, and cyclopentyl cations, J. Am. Chem. Soc., 1975, 97, 1579. [all data]

Rang, Paldoia, et al., 1974
Rang, S.; Paldoia, P.; Talvari, A., Ionization potentials of unsaturated hydrocarbons. 2. Mono-substituted cyclopentenes and cyclohexenes, Eesti. NSV Tead. Akad. Toim., 1974, 354. [all data]

Praet, 1970
Praet, M.-Th., Ionisation et dissociation du 1-methyl-cyclopentene, du methylenecyclopentane et de quelques isomeres par impact d'electrons et de photons, Org. Mass Spectrom., 1970, 4, 65. [all data]

Lewis and Hamill, 1970
Lewis, D.; Hamill, W.H., Excited states of neutral molecular fragments from appearance potentials by electron impact in a mass spectrometer, J. Chem. Phys., 1970, 52, 6348. [all data]

Demeo and Yencha, 1970
Demeo, D.A.; Yencha, A.J., Photoelectron spectra of bicyclic and exocyclic olefins, J. Chem. Phys., 1970, 53, 4536. [all data]

Demeo and El-Sayed, 1970
Demeo, D.A.; El-Sayed, M.A., Ionization potential and structure of olefins, J. Chem. Phys., 1970, 52, 2622. [all data]

Bischof and Heilbronner, 1970
Bischof, P.; Heilbronner, E., Photoelektron-Spektren von Cycloalkenen und Cycloalkadienen, Helv. Chim. Acta, 1970, 53, 1677. [all data]

Winters and Collins, 1969
Winters, R.E.; Collins, J.H., Mass spectrometric studies of structural isomers. II.Mono- and bicyclic C6H10 molecules, Org. Mass Spectrom., 1969, 2, 299. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Lambert, Xue, et al., 1986
Lambert, J.B.; Xue, L.; Bosch, R.J.; Taba, K.M.; Marko, D.E.; Urano, S.; LeBreton, P.R., Through space interactions of double bonds by photoelectron spectroscopy, J. Am. Chem. Soc., 1986, 108, 7575. [all data]

Kobayashi, 1978
Kobayashi, T., A new rule for photoelectron angular distributions of molecules, Phys. Lett. A, 1978, 69, 31. [all data]

Hentrich, Gunkel, et al., 1974
Hentrich, G.; Gunkel, E.; Klessinger, M., Photoelektronenspektren organischer verbindungen. 4. Photoelektronenspektren ungesattigter carbonylverbindungen, J. Mol. Struct., 1974, 21, 231. [all data]

Clary, Lewis, et al., 1974
Clary, D.C.; Lewis, A.A.; Morland, D.; Murrell, J.N.; Heilbronner, E., Ionization potentials of cycloalkenes, J. Chem. Soc. Faraday Trans. 2, 1974, 70, 1889. [all data]

Asmus and Klessinger, 1974
Asmus, P.; Klessinger, M., Photoelectron spectra of organic compounds. VI. Exocyclic methylene compounds, Tetrahedron, 1974, 30, 2477. [all data]

Lossing and Traeger, 1975, 2
Lossing, F.P.; Traeger, J.C., Free radicals by mass spectrometry XLVI. Heats of formation of C5H7 and C5H9 radicals and cations., J. Am. Chem. Soc., 1975, 19, 9. [all data]

Lee and Squires, 1986
Lee, R.E.; Squires, R.R., Anionic homoaromaticity: A gas phase experimental study, J. Am. Chem. Soc., 1986, 105, 5078. [all data]


Notes

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