Succinic anhydride
- Formula: C4H4O3
- Molecular weight: 100.0728
- IUPAC Standard InChI: InChI=1S/C4H4O3/c5-3-1-2-4(6)7-3/h1-2H2
- IUPAC Standard InChIKey: RINCXYDBBGOEEQ-UHFFFAOYSA-N
- CAS Registry Number: 108-30-5
- 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: 2,5-Furandione, dihydro-; Butanedioic anhydride; Dihydro-2,5-furandione; Succinic acid anhydride; Succinyl anhydride; Succinyl oxide; Tetrahydro-2,5-dioxofuran; 2,5-Diketotetrahydrofuran; Bernsteinsaure-anhydrid; NCI-C55696; 2,5(3H,4H)-Furandione; 2,5-Dioxotetrahydrofuran; Dihydro-2,5-diketotetrahydrofuran; NSC 8518; Rikacid SA; Tetrahydro-2,5-furandione
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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
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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 |
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
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.84 | PE | Kimura, Katsumata, et al., 1981 | Vertical value |
| 10.84 | PE | Worley, Gerson, et al., 1978 | Vertical value |
| 10.84 | PE | Gerson, Worley, et al., 1978 | Vertical value |
| 10.8 | PE | Almemark, Backvall, et al., 1974 | Vertical value |
Gas Chromatography
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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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | 1022. | Brandi, Bar, et al., 2011 | Program: not specified |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Worley, Gerson, et al., 1978
Worley, S.D.; Gerson, S.H.; Bodor, N.; Kaminski, J.J.; Flechtner, T.W.,
On the structure of N-chlorosuccinimide and N-bromosuccinimide. A photoelectron spectroscopic study,
J. Chem. Phys., 1978, 68, 1313. [all data]
Gerson, Worley, et al., 1978
Gerson, S.H.; Worley, S.D.; Bodor, N.; Kaminski, J.J.; Flechtner, T.W.,
The photoelectron spectra of some heterocyclic compounds which contain N, O, Cl, and Br,
J. Electron Spectrosc. Relat. Phenom., 1978, 13, 421. [all data]
Almemark, Backvall, et al., 1974
Almemark, M.; Backvall, J.E.; Moberg, C.A.; Akermark, B.; Asbrink, L.; Roos, B.,
Ab initio calculations and assignment of photoelectron spectra of maleic and succinic anhydride,
Tetrahedron, 1974, 30, 2503. [all data]
Brandi, Bar, et al., 2011
Brandi, F.; Bar, E.; Mourgues, F.; Horvath, G.; Turcsi, E.; Giuliano, G.; Liverani, A.; Tartarini, S.; Lewinsohn, E.; Rosati, C.,
Study of Redhaven peach and its white-fleshed mutant suggests a key role of CCD4 carotenoid dioxygenase in carotenoid and norisoprenoid volatile metabolism,
BMC Plant Biol., 2011, 11, 24, 1-14. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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