2-Propynoic acid, methyl ester

• Formula: C₄H₄O₂
• Molecular weight: 84.0734
• IUPAC Standard InChI: InChI=1S/C4H4O2/c1-3-4(5)6-2/h1H,2H3 Copy

  
• IUPAC Standard InChIKey: IMAKHNTVDGLIRY-UHFFFAOYSA-N Copy
• CAS Registry Number: 922-67-8
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
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• Other names: Propiolic acid, methyl ester; Methyl acetylenecarboxylate; Methyl ethynecarboxylate; Methyl propiolate; Methyl propynoate; Acetylenecarboxylic acid methyl ester; Propynoic acid, methyl ester; NSC 154164
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• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
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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:
B - John E. Bartmess
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

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Individual Reactions

C₄H₃O₂^- +  =

By formula: C₄H₃O₂^- + H⁺ = C₄H₄O₂

 +  = C₂₄H₁₈O₃

By formula: C₂₀H₁₄O + C₄H₄O₂ = C₂₄H₁₈O₃

2 +  =

By formula: 2H₂ + C₄H₄O₂ = C₄H₈O₂

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

Ionization energy determinations

De-protonation reactions

C₄H₃O₂^- +  =

By formula: C₄H₃O₂^- + H⁺ = C₄H₄O₂

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.

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]

Samuilov, Nurullina, et al., 1983
Samuilov, Ya.D.; Nurullina, R.L.; Konovalov, A.I., Thermochemical and kinetic study of the Diels-Alder reaction with ethylene and acetylene dienophiles, Zh. Org. Khim., 1983, 19, 1431-1435. [all data]

Flitcroft and Skinner, 1958
Flitcroft, T.L.; Skinner, H.A., Heats of hydrogenation Part 2.-Acetylene derivatives, Trans. Faraday Soc., 1958, 54, 47-53. [all data]

Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W., 30.4-nm He(II) photoelectron spectra of organic molecules, J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]

Notes

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

• Symbols used in this document:
  

  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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