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)
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
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Reaction thermochemistry data

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 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, Reaction thermochemistry 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

References

Go To: Top, 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.

Larson and McMahon, 1982
Larson, J.W.; McMahon, T.B., Formation, Thermochemistry, and Relative Stabilities of Proton - Bound dimers of Oxygen n - Donor Bases from Ion Cyclotron Resonance Solvent - Exchange Equilibria Measurements, J. Am. Chem. Soc., 1982, 104, 23, 6255, https://doi.org/10.1021/ja00387a016 . [all data]

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Grimsrud, E.P.; Kebarle, P., Gas Phase Ion Equilibria Studies of the Solvation of the Hydrogen Ion by Methanol, Dimethyl Ether and Water. Effect of Hydrogen Bonding, J. Am. Chem. Soc., 1973, 95, 24, 7939, https://doi.org/10.1021/ja00805a002 . [all data]

Lias, Liebman, et al., 1984
Lias, S.G.; Liebman, J.F.; Levin, R.D., Evaluated gas phase basicities and proton affinities of molecules heats of formation of protonated molecules, J. Phys. Chem. Ref. Data, 1984, 13, 695. [all data]

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Keesee, R.G.; Castleman, A.W., Jr., Thermochemical data on Ggs-phase ion-molecule association and clustering reactions, J. Phys. Chem. Ref. Data, 1986, 15, 1011. [all data]

Chyall, Brickhouse, et al., 1994
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Zimmerman, A.H.; Reed, K.J.; Brauman, J.I., Photodetachment of electrons from enolate anions. Gas phase electron affinities of enolate radicals, J. Am. Chem. Soc., 1977, 99, 7203. [all data]

Stone and Splinter, 1984
Stone, J.A.; Splinter, D.E., A high-pressure mass spectrometric study of the binding of (CH₃)₃Sn⁺ to lewis bases in the gas phase, Int. J. Mass Spectrom. Ion Processes, 1984, 59, 169. [all data]

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Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

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Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria, J. Am. Chem. Soc., 1984, 106, 517. [all data]

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Buckley and Herington, 1965
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Dolliver, Gresham, et al., 1938
Dolliver, M.A.; Gresham, T.L.; Kistiakowsky, G.B.; Smith, E.A.; Vaughan, W.E., Heats of organic reactions. VI. Heats of hydrogenation of some oxygen-containing compounds, J. Am. Chem. Soc., 1938, 60, 440-450. [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]

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Graul, S.T.; Squires, R.R., On the Existence of Alkyl Carbanions in the Gas Phase, J. Am. Chem. Soc., 1988, 110, 2, 607, https://doi.org/10.1021/ja00210a054 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [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]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Cubberley and Mueller, 1946
Cubberley, A.H.; Mueller, M.B., Equilibrium studies on the dehydrogenation of primary and secondary alcohols. I. 2-Butanol, 2-octanol, cyclopentanol and benzyl alcohol, J. Am. Chem. Soc., 1946, 68, 1149-1151. [all data]

Kolb and Burwell, 1945
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Operti, Tews, et al., 1988
Operti, L.; Tews, E.C.; Freiser, B.S., Determination of Gas-Phase Ligand Binding Energies to Mg+ by FTMS Techniques, J. Am. Chem. Soc., 1988, 110, 12, 3847, https://doi.org/10.1021/ja00220a020 . [all data]

Wiberg and Squires, 1979
Wiberg, K.B.; Squires, R.R., Thermodynamics of hydrolysis aliphatic ketals. An entropy component of steric effects, J. Am. Chem. Soc., 1979, 101, 5512-5515. [all data]

Solly, Golden, et al., 1970
Solly, R.K.; Golden, D.M.; Benson, S.W., Kinetics and thermochemistry of the gas phase reaction of methyl ethyl ketone with iodine. II. The heat of formation and unimolecular decomposition of 2-iodo-3-butanone, Int. J. Chem. Kinet., 1970, 2, 393-407. [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]

Moision and Armentrout, 2002
Moision, R.M.; Armentrout, P.B., Experimental and Theoretical Dissection of Sodium Cation/Glycine Interactions, J. Phys. Chem A, 2002, 106, 43, 10350, https://doi.org/10.1021/jp0216373 . [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]

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Desfrancois, C.; Abdoul-Carime, H.; Khelifa, N.; Schermann, J.P., Fork 1/r to 1/r2 Potentials: Electron Exchange between Rydberg Atoms and Polar Molecules, Phys. Rev. Lett., 1994, 73, 18, 2436, https://doi.org/10.1103/PhysRevLett.73.2436 . [all data]

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McAdoo and Hudson, 1983
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Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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