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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- 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.
Reaction thermochemistry data
Go To: Top, 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:
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° | 345.4 ± 2.3 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
| ΔrH° | 329.7 ± 4.6 | kcal/mol | EIAE | Cooper and Compton, 1973 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 338.0 ± 2.0 | kcal/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° | -62.22 ± 0.11 | kcal/mol | Cm | Howard and Skinner, 1966 | solid phase; solvent: Aqueous solution; Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -62.55 ± 0.11 kcal/mol; ALS |
+ 0.5
=
+
+ 0.5
By formula: C4H4ClNO2 + 0.5H4N2 = C4H5NO2 + HCl + 0.5N2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -67.78 ± 0.07 | kcal/mol | Cm | Howard and Skinner, 1966 | solid phase; solvent: Aqueous solution; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Notes
Go To: Top, Reaction thermochemistry 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
- 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.