Fumaric Acid

• Formula: C₄H₄O₄
• Molecular weight: 116.0722
• IUPAC Standard InChI: InChI=1S/C4H4O4/c5-3(6)1-2-4(7)8/h1-2H,(H,5,6)(H,7,8)/b2-1+ Copy

  
• IUPAC Standard InChIKey: VZCYOOQTPOCHFL-OWOJBTEDSA-N Copy
• CAS Registry Number: 110-17-8
• 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.
• Species with the same structure:
  • (2E)-2-butenedioic acid
• Stereoisomers:
  • Maleic acid
• Other names: 2-Butenedioic acid (E)-; trans-Butenedioic Acid; trans-1,2-Ethylenedicarboxylic Acid; Allomaleic acid; Boletic acid; Lichenic acid; Tumaric acid; (E)-2-Butenedioic acid; (E)-HO2CCH=CHCO2H; Butenedioic acid, (E)-; Kyselina fumarova; NSC-2752; U-1149; USAF EK-P-583; 1,2-Ethenedicarboxylic acid, trans-; 1,2-Ethylenedicarboxylic acid, (E); 2-Butenedioic acid (2E)-
• Information on this page:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Phase change data
  • Mass spectrum (electron ionization)
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

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: C₄H₄O₄ + H₂ = C₄H₆O₄

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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

References

Go To: Top, 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.

Flitcroft, Skinner, et al., 1957
Flitcroft, T.; Skinner, H.A.; Whiting, M.C., Heats of hydrogenation Part 1.-Dodeca-3:9 and -5:7 Diynes, Trans. Faraday Soc., 1957, 53, 784-790. [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]

Wilhoit and Shiao, 1964
Wilhoit, R.C.; Shiao, D., Thermochemistry of biologically important compounds. Heats of combustion of solid organic acids., J. Chem. Eng. Data, 1964, 9, 595-599. [all data]

Schwabe and Wagner, 1958
Schwabe, K.; Wagner, W., Verbrennungs-und bildungswarmen von fumar- und maleinsaure, Chem. Ber., 1958, 91, 686-689. [all data]

Huffman and Fox, 1938
Huffman, H.M.; Fox, S.W., Thermal data. X. The heats of combustion and free energies, at 25°, of some organic compounds concerned in carbohydrate metabolism, J. Am. Chem. Soc., 1938, 60, 1400-1403. [all data]

Parks and Huffman, 1930
Parks, G.S.; Huffman, H.M., Thermal data on organic compounds. IX. A study of the effect of unsaturation on the heat capacities, entropies and free energies of some hydrocarbons and other compounds, J. Am. Chem. Soc., 1930, 52, 4381-4391. [all data]

Kobayashi, Yokota, et al., 1975
Kobayashi, T.; Yokota, K.; Nagakura, S., Photoelectron spectra of the cis- trans-isomers of some ethylene derivatives, Bull. Chem. Soc. Jpn., 1975, 48, 412. [all data]

Notes

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• Symbols used in this document:
  

  Cp,solid	Constant pressure heat capacity of solid
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid 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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