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:
  • Phase change data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • Ion clustering data
• Data at other public NIST sites:
  • Computational Chemistry Comparison and Benchmark Database
  • Gas Phase Kinetics Database
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Phase change data

Go To: Top, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Antoine Equation Parameters

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

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Gas phase ion energetics data

Go To: Top, Phase change data, Mass spectrum (electron ionization), 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
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
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 C₂H₂O⁺ (ion structure unspecified)

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₂HO^- +  =

By formula: C₂HO^- + H⁺ = C₂H₂O

Mass spectrum (electron ionization)

Go To: Top, Phase change 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Phase change data, 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.

Reuben, 1969
Reuben, B.G., Vapor pressure of ketene, J. Chem. Eng. Data, 1969, 14, 235. [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Reuben, 1969, 2
Reuben, Bryan G., Vapor pressure of ketene, J. Chem. Eng. Data, 1969, 14, 2, 235-236, https://doi.org/10.1021/je60041a008 . [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]

Bouchoux and Salpin, 1999
Bouchoux, J.; Salpin, J.Y., Re-evaluated gas-phase basicity and proton affinity data from the thermokinetic method, Rapid Com. Mass Spectrom., 1999, 13, 932. [all data]

Niu, Bai, et al., 1993
Niu, B.; Bai, Y.; Shirley, D.A., High resolution photoelectron spectroscopy and femtosecond intramolecular dynamics of H₂CCO⁺ and D₂CCO⁺, J. Chem. Phys., 1993, 99, 2520. [all data]

Vogt, Williamson, et al., 1978
Vogt, J.; Williamson, A.D.; Beauchamp, J.L., Properties and reactions of ketene in the gas phase by ion cyclotron resonance spectroscopy and photoionization mass spectrometry. Proton affinity, site specificity of protonation, and heat of formation of ketene, J. Am. Chem. Soc., 1978, 100, 3478. [all data]

Hall, Maier, et al., 1977
Hall, D.; Maier, J.P.; Rosmus, P., Electronic states of ketene radical cation, Chem. Phys., 1977, 24, 373. [all data]

Baker and Turner, 1969
Baker, C.; Turner, D.W., Photoelectron spectra of allene and keten; Jahn-Teller distortion in the ionisation of allene, Chem. Commun., 1969, 480. [all data]

Price, Teegan, et al., 1951
Price, W.C.; Teegan, J.P.; Walsh, A.D., The absorption spectrum of ketene in the far ultra-violet, J. Chem. Soc., 1951, 920. [all data]

Bock, Hirabayashi, et al., 1981
Bock, H.; Hirabayashi, T.; Mohmand, S., Thermische erzeugung von alkyl- und halogenketenen, Chem. Ber., 1981, 114, 2595. [all data]

Bock, Hirabayashi, et al., 1977
Bock, H.; Hirabayashi, T.; Mohmand, S.; Solouki, B., Instabile Zwischenprodukte in der Gasphase: Der thermische Zerfall von Carbonsaurechloriden RCOCl, Angew. Chem., 1977, 89, 106. [all data]

Collin and Locht, 1970
Collin, J.E.; Locht, R., Positive and negative ion formation in ketene by electron impact, Intern. J. Mass Spectrom. Ion Phys., 1970, 3, 465. [all data]

McCulloh and Dibeler, 1976
McCulloh, K.E.; Dibeler, V.H., Enthalpy of formation of methyl and methylene radicals of photoionization studies of methane and ketene, J. Chem. Phys., 1976, 64, 4445. [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]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  ΔfH(+) ion,0K	Enthalpy of formation of positive ion at 0K
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

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