Succinimide
- Formula: C4H5NO2
- Molecular weight: 99.0880
- IUPAC Standard InChI: InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
- IUPAC Standard InChIKey: KZNICNPSHKQLFF-UHFFFAOYSA-N
- CAS Registry Number: 123-56-8
- 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. - Other names: 2,5-Pyrrolidinedione; Butanimide; Succinic acid imide; Succinic imide; 2,5-Diketopyrrolidine; 2,5-Dioxopyrrolidine; Succinimide-Sauba; 3,4-Dihydropyrrole-2,5-dione; Dihydro-3-pyrroline-2,5-dione; Lubrizol 6406; NSC 11204
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Gas 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -375.5 ± 1.5 | kJ/mol | Ccb | Yan and Pilcher, 1990 | Author was aware that data differs from previously reported values; Heat of combustion NR |
| ΔfH°gas | -362.2 ± 9.3 | kJ/mol | Ccb | Steele, Chirico, et al., 1989 | Hfusion=12.32 kJ/mol |
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 as indicated in comments:
B - John E. Bartmess
ALS - 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
C4H4NO2- + =
By formula: C4H4NO2- + H+ = C4H5NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1445. ± 9.6 | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
| ΔrH° | 1379. ± 19. | kJ/mol | EIAE | Cooper and Compton, 1973 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1414. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
+ 0.5
=
+
+ 0.5
By formula: C4H4BrNO2 + 0.5H4N2 = HBr + C4H5NO2 + 0.5N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -260.3 ± 0.46 | kJ/mol | Cm | Howard and Skinner, 1966 | solid phase; solvent: Aqueous solution; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -261.7 ± 0.46 kJ/mol; ALS |
+ 0.5
=
+
+ 0.5
By formula: C4H4ClNO2 + 0.5H4N2 = C4H5NO2 + HCl + 0.5N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -283.6 ± 0.3 | kJ/mol | Cm | Howard and Skinner, 1966 | solid phase; solvent: Aqueous solution; ALS |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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, polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | RTX-Wax | 2458. | Prososki, Etzel, et al., 2007 | 30. m/0.25 mm/0.5 μm, He, 40. C @ 5. min, 10. K/min, 220. C @ 10. min |
References
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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Yan and Pilcher, 1990
Yan, Y.M.; Pilcher, G.,
Enthalpies of combustion of succinic anhydride, glutaric anhydride, and glutarimide,
J. Chem. Thermodyn., 1990, 22, 893-898. [all data]
Steele, Chirico, et al., 1989
Steele, W.V.; Chirico, R.D.; Nguyen, A.; Hossenlopp, I.A.; Smith, N.K.,
Determination of some pure compound ideal-gas enthalpies of formation,
AIChE Symp. Ser., 1989, 85, 140-162. [all data]
Cumming and Kebarle, 1978
Cumming, J.B.; Kebarle, P.,
Summary of gas phase measurements involving acids AH. Entropy changes in proton transfer reactions involving negative ions. Bond dissociation energies D(A-H) and electron affinities EA(A),
Can. J. Chem., 1978, 56, 1. [all data]
Cooper and Compton, 1973
Cooper, C.D.; Compton, R.N.,
Electron attachment and cesium collisional ionization studies of tetrafluorosuccinic and hexafluoroglutaric anhydrides: Molecular electron affinities,
J. Chem. Phys., 1973, 59, 3550. [all data]
Howard and Skinner, 1966
Howard, P.B.; Skinner, H.A.,
Thermochemistry of some reactions of aqueous hydrazine with halogens, hydrogen halides and N-halogenosuccinimides,
J. Chem. Soc. A, 1966, 1536-1540. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Prososki, Etzel, et al., 2007
Prososki, R.A.; Etzel, M.R.; Rankin, S.A.,
Solvent type affects the number, distribution, and relative quantities of volatile compounds found in sweet whey powder,
J. Dairy Sci., 2007, 90, 2, 523-531, https://doi.org/10.3168/jds.S0022-0302(07)71535-7
. [all data]
Notes
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- Symbols used in this document:
ΔfH°gas Enthalpy of formation of gas at standard conditions 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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