Ketene

• Formula: C₂H₂O
• Molecular weight: 42.0367
• IUPAC Standard InChI: InChI=1S/C2H2O/c1-2-3/h1H2 Copy

  
• IUPAC Standard InChIKey: CCGKOQOJPYTBIH-UHFFFAOYSA-N Copy
• CAS Registry Number: 463-51-4
• 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: Ethenone; Carbomethene; CH2CO; Keto-ethylene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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Reaction thermochemistry data

Go To: Top, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

(CAS Reg. No. 77213-00-4 • 4294967295) +  = CAS Reg. No. 77213-00-4

By formula: (CAS Reg. No. 77213-00-4 • 4294967295C₂H₂O) + C₂H₂O = CAS Reg. No. 77213-00-4

 +  = ( • )

By formula: F^- + C₂H₂O = (F^- • C₂H₂O)

C₂HO^- +  =

By formula: C₂HO^- + H⁺ = C₂H₂O

(C₂H₃O^- • 4294967295) +  = C₂H₃O^-

By formula: (C₂H₃O^- • 4294967295C₂H₂O) + C₂H₂O = C₂H₃O^-

(CAS Reg. No. 78944-68-0 • 4294967295) +  = CAS Reg. No. 78944-68-0

By formula: (CAS Reg. No. 78944-68-0 • 4294967295C₂H₂O) + C₂H₂O = CAS Reg. No. 78944-68-0

 +  =

By formula: HNaO + C₂H₂O = C₂H₃NaO₂

(CAS Reg. No. 64723-96-2 • 4294967295) +  = CAS Reg. No. 64723-96-2

By formula: (CAS Reg. No. 64723-96-2 • 4294967295C₂H₂O) + C₂H₂O = CAS Reg. No. 64723-96-2

(CAS Reg. No. 211040-82-3 • 4294967295) +  = CAS Reg. No. 211040-82-3

By formula: (CAS Reg. No. 211040-82-3 • 4294967295C₂H₂O) + C₂H₂O = CAS Reg. No. 211040-82-3

=  + 

By formula: C₄H₆O₂S = C₂H₂O + C₂H₄OS

(CAS Reg. No. 84148-57-2 • 4294967295) +  = CAS Reg. No. 84148-57-2

By formula: (CAS Reg. No. 84148-57-2 • 4294967295C₂H₂O) + C₂H₂O = CAS Reg. No. 84148-57-2

 +  =

By formula: C₂H₂O + C₂H₄O₂ = C₄H₆O₃

 +  =

By formula: C₂H₂O + C₄H₁₀O = C₆H₁₂O₂

 +  =

By formula: C₂H₂O + C₄H₁₀O = C₆H₁₂O₂

 +  =

By formula: C₂H₂O + C₄H₁₀O = C₆H₁₂O₂

 +  =

By formula: C₂H₂O + C₄H₁₀O = C₆H₁₂O₂

 +  =

By formula: C₂H₂O + C₃H₈O = C₅H₁₀O₂

 +  =

By formula: C₂H₂O + C₂H₄OS = C₄H₆O₂S

 +  =

By formula: C₂H₂O + C₂H₆O = C₄H₈O₂

 +  =

By formula: C₂H₂O + C₃H₈O = C₅H₁₀O₂

 +  =

By formula: C₂H₂O + CH₄O = C₃H₆O₂

References

Go To: Top, Reaction thermochemistry data, Notes

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

Marks, Brauman, et al., 1988
Marks, J.; Brauman, J.I.; Mead, R.D.; Lykke, K.R.; Lineberger, W.C., Spectroscopy and Dynamics of the Dipole Supported State of Acetyl Fluoride Enolate Anion, J. Chem. Phys., 1988, 88, 11, 6785, https://doi.org/10.1063/1.454424 . [all data]

Farid and McMahon, 1980
Farid, R.; McMahon, T.B., The gas phase acidities of fluorinated acetones. An ICR investigation of the role of fluorine substituents in the stabilization of planar carbanions, Can. J. Chem., 1980, 58, 2307. [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Bond dissociation energies of F2(-) and HF2(-). A gas-phase experimental and G2 theoretical study, J. Phys. Chem., 1995, 99, 7, 2002, https://doi.org/10.1021/j100007a034 . [all data]

Larson and McMahon, 1983
Larson, J.W.; McMahon, T.B., Strong hydrogen bonding in gas-phase anions. An ion cyclotron resonance determination of fluoride binding energetics to bronsted acids from gas-phase fluoride exchange equilibria measurements, J. Am. Chem. Soc., 1983, 105, 2944. [all data]

Arshadi, Yamdagni, et al., 1970
Arshadi, M.; Yamdagni, R.; Kebarle, P., Hydration of Halide Negative Ions in the Gas Phase. II. Comparison of Hydration Energies for the Alkali Positive and Halide Negative Ions, J. Phys. Chem., 1970, 74, 7, 1475, https://doi.org/10.1021/j100702a014 . [all data]

Oakes, Jones, et al., 1983
Oakes, J.M.; Jones, M.E.; Bierbaum, V.M.; Ellison, G.B., Photoelectron spectroscopy of CCO^- and HCCO^-, J. Phys. Chem., 1983, 87, 4810. [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Holmes and Lossing, 1982
Holmes, J.L.; Lossing, F.P., Heats of formation of the ionic and neutral enols of acetaldehyde and acetone, J. Am. Chem. Soc., 1982, 104, 2648. [all data]

Nimlos, Soderquist, et al., 1989
Nimlos, M.R.; Soderquist, J.A.; Ellison, G.B., Spectroscopy of CH3CO- and CH3CO, J. Am. Chem. Soc., 1989, 111, 20, 7675, https://doi.org/10.1021/ja00202a001 . [all data]

DePuy, Bierbaum, et al., 1985
DePuy, C.H.; Bierbaum, V.M.; Damrauer, R.; Soderquist, J.A., Gas-phase reactions of the acetyl anion, J. Am. Chem. Soc., 1985, 107, 3385. [all data]

Nuttall, Laufer, et al., 1971
Nuttall, R.L.; Laufer, A.H.; Kilday, M.V., The enthalpy of formation of ketene, J. Chem. Thermodyn., 1971, 3, 167-174. [all data]

Rice and Greenberg, 1934
Rice, F.O.; Greenberg, J., Ketene. III. Heat of formation and heat of reaction with alcohols, J. Am. Chem. Soc., 1934, 38, 2268-2270. [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]

Blake and Speis, 1974
Blake, P.G.; Speis, A., Reactions of keten. Part IV. Kinetics and thermodynamics of the gas-phase reaction: Thioacetic acid + keten = acetic Thioanhydride, J. Chem. Soc. Perkin Trans. 2, 1974, 1879-1881. [all data]

Grabowski and Cheng, 1989
Grabowski, J.J.; Cheng, X., Gas-Phase Formation of the Enolate Monoanion of Acetic Acid by Proton Abstraction, J. Am. Chem. Soc., 1989, 111, 8, 3106, https://doi.org/10.1021/ja00190a078 . [all data]

Blake, Davies, et al., 1971
Blake, P.G.; Davies, H.H.; Speis, A., Reactions of keten. Part II. The thermodynamics of the gas-phase equilibrium: acetic acid + keten = acetic anhydride, J. Chem. Soc. B, 1971, 2050-2052. [all data]

Notes

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:
  

  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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