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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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Gas phase thermochemistry 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 compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Reaction thermochemistry 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 compiled as indicated in comments:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₄H₅O^- +  =

By formula: C₄H₅O^- + H⁺ = C₄H₆O

(CAS Reg. No. 71695-01-7 • 4294967295) +  = CAS Reg. No. 71695-01-7

By formula: (CAS Reg. No. 71695-01-7 • 4294967295C₄H₆O) + C₄H₆O = CAS Reg. No. 71695-01-7

 +  =

By formula: H₂ + C₄H₆O = C₄H₈O

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

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, 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.

Guthrie, 1978
Guthrie, J.P., Equilibrium constants for a series of simple aldol condensations, and linear free energy relations with other carbonyl addition reactions, Can. J. Chem., 1978, 56, 962-973. [all data]

Kharitonov Yu.Ya., 1987
Kharitonov Yu.Ya., Thermodynamic properties of methylvinylketone calculated by statistical mechanics. Deposited at ONIITEkhim, Cherkassy, Ukraine, 16.04.87, No. 417-xn 87 (From Ref. Zh. Khim. 1987, 15 B3025DP), 1987. [all data]

Anjaneyulu Y., 1988
Anjaneyulu Y., Thermodynamic functions of some acryl derivatives, J. Indian Chem. Soc., 1988, 65, 400-403. [all data]

Dorofeeva O.V., 1997
Dorofeeva O.V., Unpublished results. Thermocenter of Russian Academy of Science, Moscow, 1997. [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]

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]

Veselova and Sul'man, 1980
Veselova, M.E.; Sul'man, E.M., Effect of the chemical structure of α,β-unsaturated esters and ketones on the selectivity of their hydrogenation, Svoistva Veshchestv i Stroenie Molekul, Kalinin, 1980, 140-143. [all data]

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]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  S°gas	Entropy of gas at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  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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