2-Butanone

• Formula: C₄H₈O
• Molecular weight: 72.1057
• IUPAC Standard InChI: InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3 Copy

  
• IUPAC Standard InChIKey: ZWEHNKRNPOVVGH-UHFFFAOYSA-N Copy
• CAS Registry Number: 78-93-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Butan-2-one; Butanone; Ethyl methyl ketone; Ketone, methyl ethyl; Methyl ethyl ketone; MEK; C2H5COCH3; Acetone, methyl-; Aethylmethylketon; 3-Butanone; Butanone 2; Ethyl methyl cetone; Ethylmethylketon; Ketone, ethyl methyl; Meetco; Methyl acetone; Metiletilchetone; Metyloetyloketon; Rcra waste number U159; UN 1193; 2-Oxobutane; 2-Butanal; 2-butanone (MEK; methyl ethyl ketone); 2-butanone (MEK)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Ion clustering data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
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Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, "lite" edition (thermophysical and thermochemical data)
• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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Condensed phase thermochemistry data

Go To: Top, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar

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

C₄H₉O⁺ +  = (C₄H₉O⁺ • )

By formula: C₄H₉O⁺ + C₄H₈O = (C₄H₉O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₅H₁₁O⁺ +  = (C₅H₁₁O⁺ • )

By formula: C₅H₁₁O⁺ + C₄H₈O = (C₅H₁₁O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₄H₈O = (C₃H₉Sn⁺ • C₄H₈O)

Free energy of reaction

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₈O = (CH₆N⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Free energy of reaction

 +  = ( • )

By formula: Cl^- + C₄H₈O = (Cl^- • C₄H₈O)

 +  =

By formula: H₂ + C₄H₈O = C₄H₁₀O

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

 +  = ( • )

By formula: NO^- + C₄H₈O = (NO^- • C₄H₈O)

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

(CAS Reg. No. 35730-33-7 • 4294967295) +  = CAS Reg. No. 35730-33-7

By formula: (CAS Reg. No. 35730-33-7 • 4294967295C₄H₈O) + C₄H₈O = CAS Reg. No. 35730-33-7

=  + 

By formula: C₄H₁₀O = H₂ + C₄H₈O

 +  = ( • )

By formula: Mg⁺ + C₄H₈O = (Mg⁺ • C₄H₈O)

 +  = 2 + 

By formula: C₆H₁₄O₂ + H₂O = 2CH₄O + C₄H₈O

 +  =  + 

By formula: HI + C₄H₇IO = I₂ + C₄H₈O

 +  =

By formula: H₂ + C₄H₆O = C₄H₈O

 +  = ( • )

By formula: Na⁺ + C₄H₈O = (Na⁺ • C₄H₈O)

Gas phase ion energetics data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Ion clustering data, References, Notes

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)

Electron affinity determinations

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

C₄H₇O^- +  =

By formula: C₄H₇O^- + H⁺ = C₄H₈O

Ion clustering data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, 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 as indicated in comments:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
B - John E. Bartmess
RCD - Robert C. Dunbar

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + C₄H₈O = (CH₆N⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type NH+-O between organics

Free energy of reaction

C₃H₉Sn⁺ +  = (C₃H₉Sn⁺ • )

By formula: C₃H₉Sn⁺ + C₄H₈O = (C₃H₉Sn⁺ • C₄H₈O)

Free energy of reaction

C₄H₉O⁺ +  = (C₄H₉O⁺ • )

By formula: C₄H₉O⁺ + C₄H₈O = (C₄H₉O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

C₅H₁₁O⁺ +  = (C₅H₁₁O⁺ • )

By formula: C₅H₁₁O⁺ + C₄H₈O = (C₅H₁₁O⁺ • C₄H₈O)

Bond type: Hydrogen bonds of the type OH-O between organics

 +  = ( • )

By formula: Cl^- + C₄H₈O = (Cl^- • C₄H₈O)

 +  = ( • )

By formula: Mg⁺ + C₄H₈O = (Mg⁺ • C₄H₈O)

 +  = ( • )

By formula: NO^- + C₄H₈O = (NO^- • C₄H₈O)

 +  = ( • )

By formula: Na⁺ + C₄H₈O = (Na⁺ • C₄H₈O)

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Notes

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

Sinke and Oetting, 1964
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Malhotra, R.; Woolf, L.A., Thermodynamic properties of butan-2-one at temperatures from 278 to 338 K and pressures from 0.1 MPa to 280 MPa; predictions for higher ketones, J. Chem. Thermodynam., 1992, 24, 1207-1217. [all data]

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Sinke and Oetting, 1964, 2
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Parks, Kennedy, et al., 1956, 2
Parks, G.S.; Kennedy, W.D.; Gates, R.R.; Mosley, J.R.; Moore, G.E.; Renquist, M.L., Thermal Data on Organic Compounds XXVI. Some Heat Capacity, Entropy and Free Energy Data for Seven Compounds Containing Oxygen, J. Am. Chem. Soc., 1956, 78, 56-9. [all data]

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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]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ρc	Critical density

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