Butanedioic acid
- Formula: C4H6O4
- Molecular weight: 118.0880
- IUPAC Standard InChI: InChI=1S/C4H6O4/c5-3(6)1-2-4(7)8/h1-2H2,(H,5,6)(H,7,8)
- IUPAC Standard InChIKey: KDYFGRWQOYBRFD-UHFFFAOYSA-N
- CAS Registry Number: 110-15-6
- 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: Succinic acid; Amber acid; Asuccin; Bernsteinsaure; Dihydrofumaric acid; Katasuccin; Wormwood acid; 1,2-Ethanedicarboxylic acid; Ethanedicarboxylic acid; Wormwood; Kyselina jantarova; Acid of amber; Ethylene succinic acid; Sal succini; Salt of amber; Succinellite; 1,4-Butanedioic acid; NSC 106449
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Reaction thermochemistry data
Go To: Top, IR Spectrum, 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
B - John E. Bartmess
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Individual Reactions
+
=
By formula: C4H4O4 + H2 = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -36.3 ± 0.2 | kcal/mol | Chyd | Skinner and Snelson, 1959 | liquid phase; solvent: Ethanol; ALS |
| ΔrH° | -36.61 ± 0.40 | kcal/mol | Chyd | Flitcroft, Skinner, et al., 1957 | liquid phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -36.4 ± 0.4 kcal/mol; ALS |
C4H5O4- + =
By formula: C4H5O4- + H+ = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 322.6 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 317.3 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase; B |
+
=
By formula: C4H4O3 + H2O = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -11.20 ± 0.02 | kcal/mol | Cm | Conn, Kistiakowsky, et al., 1942 | liquid phase; Heat of hydrolysis at 303 K; ALS |
+
=
By formula: C4H4O4 + H2 = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -31.15 ± 0.03 | kcal/mol | Chyd | Flitcroft, Skinner, et al., 1957 | liquid phase; ALS |
2 +
=
By formula: 2H2 + C4H2O4 = C4H6O4
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -86.8 ± 1.1 | kcal/mol | Chyd | Flitcroft and Skinner, 1958 | solid phase; ALS |
IR Spectrum
Go To: Top, Reaction thermochemistry data, References, Notes
Data compiled by: Coblentz Society, Inc.
- SOLID (NUJOL MULL); Not specified, most likely a grating spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLID (SPLIT MULL, FLUOROLUBE FOR 3800-1330 AND NUJOL FOR 1330-400 CM -1); BECKMAN IR-9 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Reaction thermochemistry data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Skinner and Snelson, 1959
Skinner, H.A.; Snelson, A.,
Heats of hydrogenation Part 3.,
Trans. Faraday Soc., 1959, 55, 405-407. [all data]
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]
Kumar, Prabhakar, et al., 2005
Kumar, M.R.; Prabhakar, S.; Nagaveni, V.; Vairamani, M.,
Estimation of gas-phase acidities of a series of dicarboxylic acids by the kinetic method,
Rapid Commun. Mass Spectrom., 2005, 19, 8, 1053-1057, https://doi.org/10.1002/rcm.1888
. [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]
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, IR Spectrum, 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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