2-Propynoic acid, methyl ester
- Formula: C4H4O2
- Molecular weight: 84.0734
- IUPAC Standard InChIKey: IMAKHNTVDGLIRY-UHFFFAOYSA-N
- 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
The 3d structure may be viewed using Java or Javascript. - 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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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:
B - John E. Bartmess
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
C4H3O2- + =
By formula: C4H3O2- + H+ = C4H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 358.7 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 351.0 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
+
= C24H18O3
By formula: C20H14O + C4H4O2 = C24H18O3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -29.4 | kcal/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Dichloroethane; ALS |
By formula: 2H2 + C4H4O2 = C4H8O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -79.1 ± 1.1 | kcal/mol | Chyd | Flitcroft and Skinner, 1958 | liquid phase; solvent: Ethanol; ALS |
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 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
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.3 | PE | Bieri, Asbrink, et al., 1982 | LBLHLM |
10.75 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
De-protonation reactions
C4H3O2- + =
By formula: C4H3O2- + H+ = C4H4O2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 358.7 ± 2.1 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 351.0 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale; B |
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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