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2-Butanone

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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 C4H8O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.52 ± 0.04eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)827.3kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity795.5kJ/molN/AHunter and Lias, 1998HL

Electron affinity determinations

EA (eV) Method Reference Comment
0.000999EFDDesfrancois, Abdoul-Carime, et al., 1994EA: 1.0 meV. Dipole-bound state.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.52PITraeger, 1985LBLHLM
9.7EIMcAdoo and Hudson, 1983LBLHLM
9.52PITraeger, McLouglin, et al., 1982LBLHLM
9.529 ± 0.005PEHernandez, Masclet, et al., 1977LLK
9.53 ± 0.01PEMouvier and Hernandez, 1975LLK
9.54 ± 0.03EIMouvier and Hernandez, 1975LLK
9.52PETam, Yee, et al., 1974LLK
9.54 ± 0.01PIPotapov and Sorokin, 1972LLK
9.54 ± 0.01PECocksey, Eland, et al., 1971LLK
9.51PEDewar and Worley, 1969RDSH
9.48 ± 0.02PIMurad and Inghram, 1964RDSH
9.53 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
9.54 ± 0.03PIVilesov, 1960RDSH
9.5 ± 0.1PIHurzeler, Inghram, et al., 1958RDSH
9.55 ± 0.03PIVilesov and Terenin, 1957RDSH
9.46PEOlivato, Guerrero, et al., 1984Vertical value; LBLHLM
9.49PEBenoit and Harrison, 1977Vertical value; LLK
9.56PEKimura, Katsumata, et al., 1975Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
CH3+15.49?EIPotzinger and Bunau, 1969RDSH
C2H3O+10.32C2H5PITraeger, McLouglin, et al., 1982LBLHLM
C2H3O+10.69C2H5EIMouvier and Hernandez, 1975LLK
C2H3O+10.30 ± 0.05C2H5PIPotapov and Sorokin, 1972LLK
C2H3O+10.97C2H5EIPotzinger and Bunau, 1969RDSH
C2H3O+10.3C2H5PIMurad and Inghram, 1964RDSH
C2H5+12.88?EIPotzinger and Bunau, 1969RDSH
C3H5O+9.90CH3PITraeger, 1985LBLHLM
C3H5O+10.15 ± 0.05CH3PIPotapov and Sorokin, 1972LLK
C3H5O+10.60CH3EIPotzinger and Bunau, 1969RDSH
C3H5O+10.18CH3PIMurad and Inghram, 1964, 2RDSH

De-protonation reactions

C4H7O- + Hydrogen cation = 2-Butanone

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Deltar1536. ± 12.kJ/molG+TSChyall, Brickhouse, et al., 1994gas phase; Primary and secondary sites are of equal acidity by equilibration. Acidity from Zimmerman, Reed, et al., 1977; B
Deltar1545. ± 10.kJ/molD-EAZimmerman, Reed, et al., 1977gas phase; B
Quantity Value Units Method Reference Comment
Deltar1508. ± 11.kJ/molIMREChyall, Brickhouse, et al., 1994gas phase; Primary and secondary sites are of equal acidity by equilibration. Acidity from Zimmerman, Reed, et al., 1977; B
Deltar1516. ± 11.kJ/molH-TSZimmerman, Reed, et al., 1977gas phase; B

C4H7O- + Hydrogen cation = 2-Butanone

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Deltar1678. ± 17.kJ/molCIDTGraul and Squires, 1990gas phase; B
Deltar<1711.3kJ/molCIDTGraul and Squires, 1988gas phase; B
Quantity Value Units Method Reference Comment
Deltar1646. ± 17.kJ/molH-TSGraul and Squires, 1990gas phase; B

C4H7O- + Hydrogen cation = 2-Butanone

By formula: C4H7O- + H+ = C4H8O

Quantity Value Units Method Reference Comment
Deltar1540. ± 12.kJ/molG+TSCumming and Kebarle, 1978gas phase; B
Quantity Value Units Method Reference Comment
Deltar1512. ± 8.4kJ/molIMRECumming and Kebarle, 1978gas phase; 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]

Traeger, 1985
Traeger, J.C., Heat of formation for the propanoyl cation by photoionization mass spectrometry, Org. Mass Spectrom., 1985, 20, 223. [all data]

McAdoo and Hudson, 1983
McAdoo, D.J.; Hudson, C.E., The decompositions of metastable [C4H8O]+ ions and the [C4H8O]+ potential surface, Org. Mass Spectrom., 1983, 18, 466. [all data]

Traeger, McLouglin, et al., 1982
Traeger, J.C.; McLouglin, R.G.; Nicholson, A.J.C., Heat of formation for acetyl cation in the gas phase, J. Am. Chem. Soc., 1982, 104, 5318. [all data]

Hernandez, Masclet, et al., 1977
Hernandez, R.; Masclet, P.; Mouvier, G., Spectroscopie de photoelectrons d'aldehydes et de cetones aliphatiques, J. Electron Spectrosc. Relat. Phenom., 1977, 10, 333. [all data]

Mouvier and Hernandez, 1975
Mouvier, G.; Hernandez, R., Ionisation and appearance potentials of alkylketones, Org. Mass Spectrom., 1975, 10, 958. [all data]

Tam, Yee, et al., 1974
Tam, W.-C.; Yee, D.; Brion, C.E., Photoelectron spectra of some aldehydes and ketones, J. Electron Spectrosc. Relat. Phenom., 1974, 4, 77. [all data]

Potapov and Sorokin, 1972
Potapov, V.K.; Sorokin, V.V., Kinetic energies of products of dissociative photoionization of molecules. I. Aliphatic ketones and alcohols, Khim. Vys. Energ., 1972, 6, 387. [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]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Murad and Inghram, 1964
Murad, E.; Inghram, M.G., Photoionization of aliphatic ketones, J. Chem. Phys., 1964, 40, 3263. [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]

Hurzeler, Inghram, et al., 1958
Hurzeler, H.; Inghram, M.G.; Morrison, J.D., Photon impact studies of molecules using a mass spectrometer, J. Chem. Phys., 1958, 28, 76. [all data]

Vilesov and Terenin, 1957
Vilesov, F.I.; Terenin, A.N., The photoionization of the vapors of certain organic compounds, Dokl. Akad. Nauk SSSR, 1957, 115, 744, In original 539. [all data]

Olivato, Guerrero, et al., 1984
Olivato, P.R.; Guerrero, S.A.; Modelli, A.; Granozzi, G.; Jones, D.; Distefano, G., Electronic interaction in heterosubstituted acetones studied by means of ultraviolet photoelectron and electron transmission spectroscopy, J. Chem. Soc. Perkin Trans. 2, 1984, 1505. [all data]

Benoit and Harrison, 1977
Benoit, F.M.; Harrison, A.G., Predictive value of proton affinity. Ionization energy correlations involving oxygenated molecules, J. Am. Chem. Soc., 1977, 99, 3980. [all data]

Kimura, Katsumata, et al., 1975
Kimura, K.; Katsumata, S.; Yamazaki, T.; Wakabayashi, H., UV photoelectron spectra and sum rule consideration; out-of-plane orbitals of unsaturated compounds with planar-skeleton structure, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 41. [all data]

Potzinger and Bunau, 1969
Potzinger, P.; Bunau, G.v., Empirische Beruksichtigung von Uberschussenergien bei der Auftrittspotentialbestimmung, Ber. Bunsen-Ges. Phys. Chem., 1969, 73, 466. [all data]

Murad and Inghram, 1964, 2
Murad, E.; Inghram, M.G., Thermodynamic properties of the acetyl radical and bond dissociation energies in aliphatic carbonyl compounds, J. Chem. Phys., 1964, 41, 404. [all data]

Chyall, Brickhouse, et al., 1994
Chyall, L.J.; Brickhouse, M.D.; Schnute, M.E.; Squires, R.R., Kinetic versus thermodynamic control in the deprotonation of unsymmetrical ketones in the gas phase, J. Am. Chem. Soc., 1994, 116, 19, 8681, https://doi.org/10.1021/ja00098a031 . [all data]

Zimmerman, Reed, et al., 1977
Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [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]

Graul and Squires, 1988
Graul, S.T.; Squires, R.R., On the Existence of Alkyl Carbanions in the Gas Phase, J. Am. Chem. Soc., 1988, 110, 2, 607, https://doi.org/10.1021/ja00210a054 . [all data]

Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P., Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A), Can. J. Chem., 1978, 56, 1. [all data]


Notes

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