Fumaric Acid
- Formula: C4H4O4
- Molecular weight: 116.0722
- IUPAC Standard InChIKey: VZCYOOQTPOCHFL-OWOJBTEDSA-N
- 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:
- Stereoisomers:
- 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:
- Other data available:
- Options:
Data at NIST subscription sites:
NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.
Condensed phase thermochemistry data
Go To: Top, Phase change 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 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 | -810.2 ± 1.3 | kJ/mol | Chyd | Flitcroft, Skinner, et al., 1957 | Reanalyzed by Cox and Pilcher, 1970, Original value = -812.0 ± 0.4 kJ/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔfH°solid | -811.03 ± 0.88 | kJ/mol | Ccb | Wilhoit and Shiao, 1964 | ALS |
ΔfH°solid | -810.98 | kJ/mol | Ccb | Schwabe and Wagner, 1958 | ALS |
ΔfH°solid | -812.24 | kJ/mol | Ccb | Huffman and Fox, 1938 | Author's hf298_condensed=-194.88 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -1334.7 ± 0.8 | kJ/mol | Ccb | Wilhoit and Shiao, 1964 | Corresponding ΔfHºsolid = -810.98 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1334.7 | kJ/mol | Ccb | Schwabe and Wagner, 1958 | Corresponding ΔfHºsolid = -810.94 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
ΔcH°solid | -1333.5 | kJ/mol | Ccb | Huffman and Fox, 1938 | Author's hf298_condensed=-194.88 kcal/mol; Corresponding ΔfHºsolid = -812.20 kJ/mol (simple calculation by NIST; no Washburn corrections); ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°solid,1 bar | 166.1 | J/mol*K | N/A | Parks and Huffman, 1930 | Extrapolation below 90 K, 51.51 J/mol*K.; DH |
Constant pressure heat capacity of solid
Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
141.8 | 297.1 | Parks and Huffman, 1930 | T = 91 to 297.1 K. Value is unsmoothed experimental datum.; DH |
Phase change 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 as indicated in comments:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tfus | 560.45 | K | N/A | Wilhoit and Shiao, 1964, 2 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 562.55 | K | N/A | Wilhoit and Shiao, 1964, 2 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 375. | K | N/A | Timmermans, 1935 | Uncertainty assigned by TRC = 2. K; TRC |
Tfus | 473. | K | N/A | Kern, Shriner, et al., 1925 | Uncertainty assigned by TRC = 4. K; TRC |
Tfus | 557.15 | K | N/A | Weiss and Downs, 1923 | Uncertainty assigned by TRC = 4. K; TRC |
Enthalpy of sublimation
ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
123.6 ± 2.0 | 381. | TE,ME | De Kruif and Van Ginkel, 1977 | Based on data from 371. to 391. K.; AC |
136. ± 6.3 | 365. | QF | Wolf and Weghofer, 1938 | See also Trieschmann, 1935 and Jones, 1960.; AC |
136. ± 6.3 | 365. | V | Wolf and Weghofer, 1938, 2 | ALS |
134. ± 4.2 | 358. to 371. | N/A | Wolf and Trieschmann, 1934 | AC |
Reaction thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -130.3 ± 0.1 | kJ/mol | Chyd | Flitcroft, Skinner, et al., 1957 | liquid phase |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change data, 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 by: Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.7 | PE | Kobayashi, Yokota, et al., 1975 | |
10.9 | PE | Kobayashi, Yokota, et al., 1975 | Vertical value |
References
Go To: Top, Condensed phase thermochemistry data, Phase change 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]
Wilhoit and Shiao, 1964, 2
Wilhoit, R.C.; Shiao, D.,
Thermochemistry of Biologically Important Compounds. Heats of Combustion of Solid Organic Acids,
J. Chem. Eng. Data, 1964, 9, 595. [all data]
Timmermans, 1935
Timmermans, J.,
Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds.,
Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]
Kern, Shriner, et al., 1925
Kern, J.W.; Shriner, R.L.; Adams, R.,
Platinum and Palladium Oxides as Catalysts in the Reduction of Organic Compounds IX. The Reduction of Olefins,
J. Am. Chem. Soc., 1925, 47, 1147. [all data]
Weiss and Downs, 1923
Weiss, J.M.; Downs, C.R.,
The Physical Properties of Maleic, Fumaric and Malic Acids,
J. Am. Chem. Soc., 1923, 45, 1003. [all data]
De Kruif and Van Ginkel, 1977
De Kruif, C.G.; Van Ginkel, C.H.D.,
Torsion-weighing effusion vapour-pressure measurements on organic compounds,
The Journal of Chemical Thermodynamics, 1977, 9, 8, 725-730, https://doi.org/10.1016/0021-9614(77)90015-5
. [all data]
Wolf and Weghofer, 1938
Wolf, K.L.; Weghofer, H.Z.,
Z. Phys. Chem. Abt. B, 1938, 39, 194. [all data]
Trieschmann, 1935
Trieschmann, H.G.,
, Ph.D. Dissertation, Inst. Fur Phys. Chem. and Electrochem. der Universitat Kiel, Germany, 1935. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Wolf and Weghofer, 1938, 2
Wolf, K.L.; Weghofer, H.,
Uber sublimationswarmen,
Z. Phys. Chem., 1938, 39, 194-208. [all data]
Wolf and Trieschmann, 1934
Wolf, K.L.; Trieschmann, H.G.,
Z. Phys. Chem. Abt. B, 1934, 27, 376. [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
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, References
- 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) Tfus Fusion (melting) point 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 ΔsubH Enthalpy of sublimation - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
- The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
- Customer support for NIST Standard Reference Data products.