2-Butenedioic acid, 2-methyl-, (E)-
- Formula: C5H6O4
- Molecular weight: 130.0987
- IUPAC Standard InChI: InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2+
- IUPAC Standard InChIKey: HNEGQIOMVPPMNR-NSCUHMNNSA-N
- CAS Registry Number: 498-24-8
- 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. - Stereoisomers:
- Other names: Mesaconic acid; trans-1-Propene-1,2-dicarboxylic acid; trans-2-Methyl-2-butenedioic acid; Methylfumaric acid; 2-Methylfumaric acid; (E)-2-Methyl-2-butenedioic acid; Butenedioic acid, methyl-, (E)-; Fumaric acid, methyl-; Mesaconate; Kyselina mesakonova; 2-Butenedioic acid, 2-methyl-, (2E)-; NSC 65438
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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -824.4 ± 1.5 | kJ/mol | Ccb | Wilhoit and Lei, 1965 | |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -2000.6 ± 1.4 | kJ/mol | Ccb | Wilhoit and Lei, 1965 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2001.9 kJ/mol; Corresponding ΔfHºsolid = -824.42 kJ/mol (simple calculation by NIST; no Washburn corrections) |
Reaction thermochemistry data
Go To: Top, Condensed phase 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 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: C5H4O3 + H2O = C5H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -34.0 | kJ/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K |
+
=
+
By formula: C5H6O4 + Br2 = C5H6O4 + Br2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -5.1 ± 0.7 | kJ/mol | Eqk | Jwo, Huang, et al., 1987 | solid phase; HPLC |
References
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Wilhoit and Lei, 1965
Wilhoit, R.C.; Lei, I.,
Thermochemistry of biologically important compounds. Heats of combustion of five organic acids.,
J. Chem. Eng. Data, 1965, 10, 166-168. [all data]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Conn, Kistiakowsky, et al., 1942
Conn, J.B.; Kistiakowsky, G.B.; Roberts, R.M.; Smith, E.A.,
Heats of organic reactions. XIII. Heats of hydrolysis of some acid anhydrides,
J. Am. Chem. Soc., 1942, 64, 1747-17. [all data]
Jwo, Huang, et al., 1987
Jwo, J-J.; Huang, C-Y.; Chang, E-F.; Wu, R.R.,
Kinetic study of the bromine-catalyzed isomerization of methyl- and chloro-maleic acids in aqueous Ce(IV)-Br- -H2SO4 medium,
J. Chin. Chem. Soc. (Taipei), 1987, 34, 247-256. [all data]
Notes
Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References
- Symbols used in this document:
ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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