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, 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
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 |
Gas phase ion energetics data
Go To: Top, 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: John E. Bartmess
De-protonation reactions
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 |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 317.3 ± 2.0 | kcal/mol | CIDC | Kumar, Prabhakar, et al., 2005 | gas phase |
References
Go To: Top, 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.
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, Gas phase ion energetics data, 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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