2-Propenoic acid, methyl ester
- Formula: C4H6O2
- Molecular weight: 86.0892
- IUPAC Standard InChI: InChI=1S/C4H6O2/c1-3-4(5)6-2/h3H,1H2,2H3
- IUPAC Standard InChIKey: BAPJBEWLBFYGME-UHFFFAOYSA-N
- CAS Registry Number: 96-33-3
- 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: Acrylic acid methyl ester; Methoxycarbonylethylene; Methyl acrylate; Methyl propenoate; Methyl 2-propenoate; CH2=CHCOOCH3; Methyl propenate; Acrylate de methyle; Acrylsaeuremethylester; Methyl-acrylat; Methylacrylaat; Metilacrilato; Curithane 103; Methylester kyseliny akrylove; UN 1919; Methyl prop-2-enoate; Methyl ester of 2-propenoic acid; Methyl ester acrylic acid; NSC 24146
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -333.0 | kJ/mol | Ccr | Hall and Baldt, 1971 |
Condensed phase 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -362.2 | kJ/mol | Ccr | Hall and Baldt, 1971 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°liquid | -2069.4 ± 0.67 | kJ/mol | Ccr | Hall and Baldt, 1971 | Corresponding ΔfHºliquid = -362.2 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 172.3 | 298.15 | Karabaev, Saidov, et al., 1985 | T = 90 to 290 K. Cp(c) = 285.21 + 5.32T J/kg*K (103 to 175 K; Cp(liq) = 1568.62 + 1.45T (197.5 to 290 K). Cp data calculated from equation.; DH |
| 161.5 | 298.15 | Fuchs, 1979 | DH |
| 133.4 | 297. | Hall and Baldt, 1971 | DH |
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: 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
+
=
By formula: H2 + C4H6O2 = C4H8O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -501.2 | kJ/mol | Chyd | Veselova and Sul'man, 1980 | liquid phase |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
Data compiled as indicated in comments:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Proton affinity (review) | 825.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
| Quantity | Value | Units | Method | Reference | Comment |
| Gas basicity | 794.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.9 | PE | Van Dam and Oskam, 1978 | LLK |
| 10.74 | PE | Van Dam and Oskam, 1978 | Vertical value; LLK |
| 10.72 | PE | Sustmann and Trill, 1972 | Vertical value; LLK |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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.
Hall and Baldt, 1971
Hall, H.K., Jr.; Baldt, J.H.,
Thermochemistry of strained-ring bridgehead nitriles and esters,
J. Am. Chem. Soc., 1971, 93, 140-145. [all data]
Karabaev, Saidov, et al., 1985
Karabaev, M.; Saidov, A.A.; Abduzhaminov, T.P.; Kenisarin, M.M.,
Heat capacity and molecular kinetic processes of condensed phase acrylates and methacrylates, Izv. Akad. Nauk UzSSR,
Ser. Fiz.-Math., 1985, (6), 51-54. [all data]
Fuchs, 1979
Fuchs, R.,
Heat capacities of some liquid aliphatic, alicyclic, and aromatic esters at 298.15 K,
J. Chem. Thermodyn., 1979, 11, 959-961. [all data]
Veselova and Sul'man, 1980
Veselova, M.E.; Sul'man, E.M.,
Effect of the chemical structure of α,β-unsaturated esters and ketones on the selectivity of their hydrogenation,
Svoistva Veshchestv i Stroenie Molekul, Kalinin, 1980, 140-143. [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]
Van Dam and Oskam, 1978
Van Dam, H.; Oskam, A.,
He(I) and He(II) photoelectron spectra of some substituted ethylenes,
J. Electron Spectrosc. Relat. Phenom., 1978, 13, 273. [all data]
Sustmann and Trill, 1972
Sustmann, R.; Trill, H.,
Photoelektronenspektroskopische Bestimmung von Substituenten-Effekten. II. α,β-ungesattigte Carbonester,
Tetrahedron Lett., 1972, 42, 4271. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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