Succinimide
- Formula: C4H5NO2
- Molecular weight: 99.0880
- 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
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, 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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -89.75 ± 0.36 | kcal/mol | Ccb | Yan and Pilcher, 1990 | Author was aware that data differs from previously reported values; Heat of combustion NR |
ΔfH°gas | -86.6 ± 2.2 | kcal/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 | -110.00 ± 0.072 | kcal/mol | Ccb | Steele, Chirico, et al., 1989 | Hfusion=12.32 kJ/mol; ALS |
ΔfH°solid | -109.72 ± 0.07 | kcal/mol | Ccb | Coleman and Skinner, 1966 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°solid | -436.989 ± 0.057 | kcal/mol | Ccb | Steele, Chirico, et al., 1989 | Hfusion=12.32 kJ/mol; ALS |
ΔcH°solid | -437.28 ± 0.05 | kcal/mol | Ccb | Coleman and Skinner, 1966 | ALS |
Constant pressure heat capacity of solid
Cp,solid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
29.608 | 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 |
31.41 | 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° | 20.0 ± 0.36 | kcal/mol | N/A | Meng-Yan and Pilcher, 1990 | AC |
ΔsubH° | 20.0 ± 0.36 | kcal/mol | C | Yan and Pilcher, 1990 | Author was aware that data differs from previously reported values; Heat of combustion NR; ALS |
ΔsubH° | 23.4 ± 1.1 | kcal/mol | V | Steele, Chirico, et al., 1989 | Hfusion=12.32 kJ/mol; ALS |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
16.0 | 431. | A | Stephenson and Malanowski, 1987 | Based on data from 416. to 561. K.; AC |
17.6 | 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 (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
388. to 560.7 | 4.97811 | 2365.906 | -86.489 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of sublimation
ΔsubH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
19.9 ± 0.36 | 329. | ME | Meng-Yan and Pilcher, 1990 | Based on data from 317. to 340. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
4.0631 | 400. | Steele, Chirico, et al., 1989 | DH |
4.06 | 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° | 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 |
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 |
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 |
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 as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.01 | PE | Worley, Gerson, et al., 1978 | Vertical value; LLK |
10.01 | PE | Gerson, Worley, et al., 1978 | Vertical value; LLK |
De-protonation 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 |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
Mass spectrum (electron ionization)
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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
Spectrum
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Additional Data
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Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Japan AIST/NIMC Database- Spectrum MS-NW- 421 |
NIST MS number | 228398 |
UV/Visible spectrum
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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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
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Source | Saidel, 1953 |
---|---|
Owner | INEP CP RAS, NIST OSRD Collection (C) 2007 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
Origin | INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS |
Source reference | RAS UV No. 786 |
Instrument | n.i.g. |
Melting point | 126.5 |
Boiling point | 287 dec |
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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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]
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]
Saidel, 1953
Saidel, L.J.,
Contribution of the ultra-violet absorption spectrum of asparagine to the problem of its structure,
Nature (London), 1953, 172, 955-956. [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
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, 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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