Methyl vinyl ketone

• Formula: C₄H₆O
• Molecular weight: 70.0898
• IUPAC Standard InChI: InChI=1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3 Copy

  
• IUPAC Standard InChIKey: FUSUHKVFWTUUBE-UHFFFAOYSA-N Copy
• CAS Registry Number: 78-94-4
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: 3-Buten-2-one; Vinyl methyl ketone; 1-Buten-3-one; 2-Butenone; 3-Butene-2-one; CH2=CHCOCH3; Acetone, methylene-; Butenone; Ketone, methyl vinyl; Methyl ethenyl ketone; Methyl-vinyl-cetone; Methylvinylketon; Acetyl ethylene; Methylene acetone; γ-Oxo-α-butylene; UN 1251; 3-Oxobutene; 3-Butenen-2-one; But-3-en-2-one; 3-Oxo-1-butene; NSC 4853
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• Information on this page:
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₅O^- +  =

By formula: C₄H₅O^- + H⁺ = C₄H₆O

Mass spectrum (electron ionization)

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

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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