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2-Butanone, 3-methyl-

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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
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 C5H10O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.31 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)199.9kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity192.3kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.298 ± 0.005PEHernandez, Masclet, et al., 1977LLK
9.30 ± 0.01PEMouvier and Hernandez, 1975LLK
9.30 ± 0.04EIMouvier and Hernandez, 1975LLK
9.36PETam, Yee, et al., 1974LLK
9.30 ± 0.01PECocksey, Eland, et al., 1971LLK
9.30 ± 0.02PIMurad and Inghram, 1964RDSH
9.32 ± 0.02PIWatanabe, Nakayama, et al., 1962RDSH

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+10.68?EIMouvier and Hernandez, 1975LLK
C2H3O+10.4iso-C3H7PIMurad and Inghram, 1964RDSH
C4H7O+9.9?EIMouvier and Hernandez, 1975LLK
C4H7O+9.94CH3PIMurad and Inghram, 1964RDSH

De-protonation reactions

C5H9O- + Hydrogen cation = 2-Butanone, 3-methyl-

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar369.3 ± 2.7kcal/molG+TSChyall, Brickhouse, et al., 1994gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol; B
Quantity Value Units Method Reference Comment
Deltar362.8 ± 2.5kcal/molIMREChyall, Brickhouse, et al., 1994gas phase; By equilibration, more substituted site is less acidic than Me by 2.3 kcal/mol; B

C5H9O- + Hydrogen cation = 2-Butanone, 3-methyl-

By formula: C5H9O- + H+ = C5H10O

Quantity Value Units Method Reference Comment
Deltar367.3 ± 2.2kcal/molG+TSCumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; B
Quantity Value Units Method Reference Comment
Deltar360.5 ± 2.0kcal/molIMRECumming and Kebarle, 1978gas phase; Structure assignment revised to less-substituted site: Chyall, Brickhouse, et al., 1994; 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]

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]

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]

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]

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]

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

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