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) Copy

  
• IUPAC Standard InChIKey: KZNICNPSHKQLFF-UHFFFAOYSA-N Copy
• 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
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• 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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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
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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

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

Constant pressure heat capacity of solid

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

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas; HP-GC/MS/IRD

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

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

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

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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]

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]

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

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• 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
  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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