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 |
Condensed 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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°solid | -460.25 ± 0.30 | kJ/mol | Ccb | Steele, Chirico, et al., 1989 | Hfusion=12.32 kJ/mol; ALS |
| ΔfH°solid | -459.1 ± 0.3 | kJ/mol | Ccb | Coleman and Skinner, 1966 | ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔcH°solid | -1828.36 ± 0.24 | kJ/mol | Ccb | Steele, Chirico, et al., 1989 | Hfusion=12.32 kJ/mol; ALS |
| ΔcH°solid | -1829.6 ± 0.2 | kJ/mol | Ccb | Coleman and Skinner, 1966 | ALS |
Constant pressure heat capacity of solid
| Cp,solid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 123.88 | 298.15 | Steele, Chirico, et al., 1989 | T = 305 to 495 K. Csat/R(c) = 0.0438T + 1.87 (305 to 355 K); Csat/R(liq) = 0.0265T + 13.38 (405 to 495 K).; DH |
| 131.4 | 323. | Satoh and Sogabe, 1941 | T = 0 to 100°C. Mean value.; DH |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tboil | 560.7 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
| Quantity | Value | Units | Method | Reference | Comment |
| Tfus | 400. | K | N/A | Sorum and Durand, 1952 | Uncertainty assigned by TRC = 1.5 K; TRC |
| Tfus | 398.15 | K | N/A | Cowley and Partington, 1936 | Uncertainty assigned by TRC = 0.6 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔsubH° | 83.6 ± 1.5 | kJ/mol | N/A | Meng-Yan and Pilcher, 1990 | AC |
| ΔsubH° | 83.6 ± 1.5 | kJ/mol | C | Yan and Pilcher, 1990 | Author was aware that data differs from previously reported values; Heat of combustion NR; ALS |
| ΔsubH° | 98.1 ± 4.5 | kJ/mol | V | Steele, Chirico, et al., 1989 | Hfusion=12.32 kJ/mol; ALS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 66.9 | 431. | A | Stephenson and Malanowski, 1987 | Based on data from 416. to 561. K.; AC |
| 73.5 | 403. | N/A | Stull, 1947 | Based on data from 388. to 560. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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| Temperature (K) | A | B | C | Reference | Comment |
|---|---|---|---|---|---|
| 388. to 560.7 | 4.98382 | 2365.906 | -86.489 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
| ΔsubH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 83.1 ± 1.5 | 329. | ME | Meng-Yan and Pilcher, 1990 | Based on data from 317. to 340. K.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 17.000 | 400. | Steele, Chirico, et al., 1989 | DH |
| 17.0 | 400. | Domalski and Hearing, 1996 | AC |
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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Notes
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]
Coleman and Skinner, 1966
Coleman, D.J.; Skinner, H.A.,
Heats of combustion of organic compounds of nitrogen. Part 4.- Succinimide, N,N'-bisuccinimide and 2,5,2',5'-tetramethyl-dipyrryl-(1,1'),
Trans. Faraday Soc., 1966, 62, 2057-2062. [all data]
Satoh and Sogabe, 1941
Satoh, S.; Sogabe, T.,
The heat capacities of some organic compounds containing nitrogen and the atomic heat of nitrogen. (4), Sci.,
Pap. Inst. Phys. Chem. Res. (Tokyo), 1941, 38, 246-251. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Sorum and Durand, 1952
Sorum, C.H.; Durand, E.A.,
The Melting of Binary Eutectics,
J. Am. Chem. Soc., 1952, 74, 1071. [all data]
Cowley and Partington, 1936
Cowley, E.G.; Partington, J.R.,
Studies in dielectric polarisation. Part XV. The dipole moments of fivemembered nitrogen ring compounds: indole,skatole,carbazole,isatin, phthalimide, and succinimide.,
J. Chem. Soc., 1936, 1936, 47. [all data]
Meng-Yan and Pilcher, 1990
Meng-Yan, Yang; Pilcher, G.,
Enthalpies of combustion of succinic anhydride, glutaric anhydride, and glutarimide,
The Journal of Chemical Thermodynamics, 1990, 22, 9, 893-898, https://doi.org/10.1016/0021-9614(90)90177-R
. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Stull, 1947
Stull, Daniel R.,
Vapor Pressure of Pure Substances. Organic and Inorganic Compounds,
Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References
- Symbols used in this document:
Cp,solid Constant pressure heat capacity of solid Tboil Boiling point Tfus Fusion (melting) point ΔcH°solid Enthalpy of combustion of solid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°solid Enthalpy of formation of solid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔsubH Enthalpy of sublimation ΔsubH° Enthalpy of sublimation at standard conditions ΔvapH Enthalpy of vaporization - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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