3-Butyn-2-one

• Formula: C₄H₄O
• Molecular weight: 68.0740
• IUPAC Standard InChI: InChI=1S/C4H4O/c1-3-4(2)5/h1H,2H3 Copy

  
• IUPAC Standard InChIKey: XRGPFNGLRSIPSA-UHFFFAOYSA-N Copy
• CAS Registry Number: 1423-60-5
• 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: Methyl ethynyl ketone; 1-Butyn-3-one; Ketone, ethynyl methyl; Ethynyl methyl ketone; Acetylacetylene; Acetylethyne; But-3-yn-2-one; 3-Butyne-2-one
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• Information on this page:
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • IR Spectrum
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Phase change 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 by: Robert L. Brown and Stephen E. Stein

Reduced pressure boiling point

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 by: John E. Bartmess

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

C₄H₃O^- +  =

By formula: C₄H₃O^- + H⁺ = C₄H₄O

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 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 C₄H₄O⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₄H₃O^- +  =

By formula: C₄H₃O^- + H⁺ = C₄H₄O

Mass spectrum (electron ionization)

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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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Phase change data, Reaction thermochemistry 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.

Farchan Laboratories, 1990
Farchan Laboratories, Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D., The Nature and Analysis of Substituent Effects, Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Burgers, Holmes, et al., 1982
Burgers, P.C.; Holmes, J.L.; Lossing, F.P.; Mommers, A.A.; Povel, F.R.; Terlouw, J.K., Isomeric and tautomeric [C₄H₄O]⁺ ions. Their thermochemistry and collisionally induced fragmentation characteristics, Can. J. Chem., 1982, 60, 2246. [all data]

Willett and Baer, 1980
Willett, G.D.; Baer, T., Thermochemistry and dissociation dynamics of state-selected C₄H₄X ions. 2. Furan 3-butyn-2-one, J. Am. Chem. Soc., 1980, 102, 6769. [all data]

Terlouw, Burgers, et al., 1979
Terlouw, J.K.; Burgers, P.C.; Holmes, J.L., Thermochemistry and generation of vinylketene, J. Am. Chem. Soc., 1979, 101, 225. [all data]

Holmes and Terlouw, 1979
Holmes, J.L.; Terlouw, J.K., Structures of [C₄H₄O]⁺ ions produced from 2- and 4-pyrone, J. Am. Chem. Soc., 1979, 101, 4973. [all data]

Carlier and Mouvier, 1979
Carlier, P.; Mouvier, G., Etude par spectrometrie de photoelectrons de la structure electronique des ynals et des ynones conjugues, J. Electron Spectrosc. Relat. Phenom., 1979, 17, 169. [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]

Mommers, Burgers, et al., 1984
Mommers, A.A.; Burgers, P.C.; Holmes, J.L.; Terlouw, J.K., Isomeric [C₃H₄]⁺ ions: Their identification and generation in dissociative ionizations, Org. Mass Spectrom., 1984, 19, 7. [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  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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