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
  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:
  • Reaction thermochemistry data
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • IR Spectrum
  • Gas Chromatography
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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, Mass spectrum (electron ionization), UV/Visible spectrum, 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

 + 0.5 =  +  + 0.5

By formula: C₄H₄BrNO₂ + 0.5H₄N₂ = HBr + C₄H₅NO₂ + 0.5N₂

 + 0.5 =  +  + 0.5

By formula: C₄H₄ClNO₂ + 0.5H₄N₂ = C₄H₅NO₂ + HCl + 0.5N₂

Mass spectrum (electron ionization)

Go To: Top, Reaction thermochemistry data, UV/Visible spectrum, 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

UV/Visible spectrum

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

Notice: This spectrum may be better viewed with a Javascript and HTML 5 enabled browser.

For Zoom

1.) Enter the desired X axis range (e.g., 100, 200)

2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

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]

Notes

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, 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.