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Cyclohexanone

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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 C6H10O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.16 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)201.0kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity193.9kcal/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.0033EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 3.3 meV. Dipole-bound state.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.18PELoudet, Grimaud, et al., 1976LLK
9.5 ± 0.2EIFortin, Forest, et al., 1973LLK
9.16 ± 0.01PECocksey, Eland, et al., 1971LLK
9.14 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
9.14 ± 0.03PIVilesov, 1960RDSH
9.29PESpanka and Rademacher, 1986Vertical value; LBLHLM
9.18PEKovac and Klasinc, 1978Vertical value; LLK
9.28PEHentrich, Gunkel, et al., 1974Vertical value; LLK
9.14 ± 0.02PEChadwick, Frost, et al., 1971Vertical value; LLK

De-protonation reactions

C6H9O- + Hydrogen cation = Cyclohexanone

By formula: C6H9O- + H+ = C6H10O

Quantity Value Units Method Reference Comment
Deltar366.4 ± 2.0kcal/molD-EABrinkman, Berger, et al., 1993gas phase; B
Deltar365.8 ± 2.3kcal/molD-EAZimmerman, Jackson, et al., 1978gas phase; B
Deltar369.0 ± 4.2kcal/molG+TSBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; B
Quantity Value Units Method Reference Comment
Deltar358.7 ± 2.3kcal/molH-TSBrinkman, Berger, et al., 1993gas phase; B
Deltar358.0 ± 2.6kcal/molH-TSZimmerman, Jackson, et al., 1978gas phase; B
Deltar361.2 ± 4.0kcal/molIMRBBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH; 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]

Desfrancois, Abdoul-Carime, et al., 1994
Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P., Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules, Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436 . [all data]

Loudet, Grimaud, et al., 1976
Loudet, M.; Grimaud, M.; Metras, F.; Pfister-Guillouzo, G., Interactions intramoleculaires en serie cyclohexanique partie II. Spectres photoelectroniques de chloro-2-cyclohexanones, J. Mol. Struct., 1976, 35, 213. [all data]

Fortin, Forest, et al., 1973
Fortin, C.J.; Forest, M.; Vaziri, C.; Gravel, D.; Rousseau, Y., Spectrometrie de masse des cyclohexanones gem-diphenylees. I. Localisation de la charge positive, Can. J. Chem., 1973, 51, 3445. [all data]

Cocksey, Eland, et al., 1971
Cocksey, B.J.; Eland, J.H.D.; Danby, C.J., The effect of alkyl substitution on ionisation potential, J. Chem. Soc., 1971, (B), 790. [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]

Vilesov, 1960
Vilesov, F.I., The photoionization of vapors of compounds whose molecules contain carbonyl groups, Dokl. Phys. Chem., 1960, 132, 521, In original 1332. [all data]

Spanka and Rademacher, 1986
Spanka, G.; Rademacher, P., Transannular interactions in difunctional medium rings. 1. n/«pi» Interactions in cyclic amino ketones and aminoalkenes studied by photoelectron spectroscopy, J. Org. Chem., 1986, 51, 592. [all data]

Kovac and Klasinc, 1978
Kovac, B.; Klasinc, L., Photoelectron spectroscopy of adamantane and some adamantanones, Croat. Chem. Acta, 1978, 51, 55. [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]

Chadwick, Frost, et al., 1971
Chadwick, D.; Frost, D.C.; Weiler, L., The photoelectron spectra of cyclic ketones, Tetrahedron Lett., 1971, 47, 4543. [all data]

Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I., Molecular Rotation and the Observation of Dipole-Bound States of Anions, J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688 . [all data]

Zimmerman, Jackson, et al., 1978
Zimmerman, A.H.; Jackson, R.L.; Janousek, B.K.; Brauman, J.J., Electron photodetachment from cyclic enolate anions in the gas phase: Electron affinities of cyclic enolate radicals, J. Am. Chem. Soc., 1978, 100, 4674. [all data]

Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R., Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions, J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002 . [all data]


Notes

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