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
- 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
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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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1501. ± 8.8 | kJ/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° | 1469. ± 8.4 | kJ/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° | -123. | kJ/mol | Kin | Samuilov, Nurullina, et al., 1983 | liquid phase; solvent: Dichloroethane; ALS |
2 +
=
By formula: 2H2 + C4H4O2 = C4H8O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -331. ± 4.6 | kJ/mol | Chyd | Flitcroft and Skinner, 1958 | liquid phase; solvent: Ethanol; ALS |
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.
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]
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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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