Methyl vinyl ketone

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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 C4H6O+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.65 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)199.5kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity191.9kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.66PEMorizur, Mercier, et al., 1982LBLHLM
9.64EITerlouw, Heerma, et al., 1980LLK
9.66PEMasclet and Mouvier, 1978LLK
10.11PEKobayashi, 1978Vertical value; LLK
9.61PETam, Yee, et al., 1974Vertical value; LLK
9.67PEHentrich, Gunkel, et al., 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C2H3O+12.40C2H3EIMajer, Patrick, et al., 1961RDSH
C3H3O+10.44 ± 0.05CH3EIHolmes, Terlouw, et al., 1980LLK
C3H3O+10.85CH3EIMajer, Patrick, et al., 1961RDSH

De-protonation reactions

C4H5O- + Hydrogen cation = Methyl vinyl ketone

By formula: C4H5O- + H+ = C4H6O

Quantity Value Units Method Reference Comment
Δr363.3 ± 2.1kcal/molG+TSBartmess and Kiplinger, 1986gas phase; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Δr356.5 ± 2.0kcal/molIMREBartmess and Kiplinger, 1986gas 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]

Morizur, Mercier, et al., 1982
Morizur, J.-P.; Mercier, J.; Sarraf, M., 2-Substituted-2,3-dihydro-4H-pyrans: Competition between 'Retro Diels-Alder' fragmentation and substituent loss, Org. Mass Spectrom., 1982, 17, 327. [all data]

Terlouw, Heerma, et al., 1980
Terlouw, J.K.; Heerma, W.; Holmes, J.L.; Burgers, P.C., Structure and formation of gaseous [C4H6O]+ ions. 1-The enolic ions [CH2=C(OH)-CH=CH2]+ and [CH2=CH-CH=CH(OH)]+ and their relationship with their keto counterparts, Org. Mass Spectrom., 1980, 15, 582. [all data]

Masclet and Mouvier, 1978
Masclet, P.; Mouvier, G., Etude par spectrometrie photoelectronique d'aldehydes et de cetones ethyleniques conjugues, J. Electron Spectrosc. Relat. Phenom., 1978, 14, 77. [all data]

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

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]

Majer, Patrick, et al., 1961
Majer, J.R.; Patrick, C.R.; Robb, J.C., Appearance potentials of the acetyl radical-ion, J. Chem. Soc. Faraday Trans., 1961, 57, 14. [all data]

Holmes, Terlouw, et al., 1980
Holmes, J.L.; Terlouw, J.K.; Burgers, P.C., [C3H3O]+ ions; Reacting and non-reacting configurations, Org. Mass Spectrom., 1980, 15, 140. [all data]

Bartmess and Kiplinger, 1986
Bartmess, J.E.; Kiplinger, J.P., 'Kinetic' vs. thermodynamic acidities of enones in the gas phase, J. Org. Chem., 1986, 51, 2173. [all data]


Notes

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