1H-Pyrrole-2,5-dione
- Formula: C4H3NO2
- Molecular weight: 97.0721
- IUPAC Standard InChI: InChI=1S/C4H3NO2/c6-3-1-2-4(7)5-3/h1-2H,(H,5,6,7)
- IUPAC Standard InChIKey: PEEHTFAAVSWFBL-UHFFFAOYSA-N
- CAS Registry Number: 541-59-3
- Chemical structure:
This structure is also available as a 2d Mol file - Other names: Maleimide; Pyrrole-2,5-dione; 3-Pyrroline-2,5-dione; Maleinimide; Maleic imide
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Reaction thermochemistry data
Go To: Top, Gas phase ion energetics data, 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 by: John E. Bartmess
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
C4H2NO2- + =
By formula: C4H2NO2- + H+ = C4H3NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1360. ± 19. | kJ/mol | EIAE | Cooper and Compton, 1973 | gas phase; From maleimide. G3MP2B3 calculations indicate a dHacid = 342 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1328. ± 21. | kJ/mol | H-TS | Cooper and Compton, 1973 | gas phase; From maleimide. G3MP2B3 calculations indicate a dHacid = 342 kcal/mol |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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 by: John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.153 ± 0.087 | TDEq | Paul and Kebarle, 1989 | ΔGea(423 K) = -26.2±1 kcal/mol, ΔS = -1±3 eu |
De-protonation reactions
C4H2NO2- + =
By formula: C4H2NO2- + H+ = C4H3NO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1360. ± 19. | kJ/mol | EIAE | Cooper and Compton, 1973 | gas phase; From maleimide. G3MP2B3 calculations indicate a dHacid = 342 kcal/mol |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1328. ± 21. | kJ/mol | H-TS | Cooper and Compton, 1973 | gas phase; From maleimide. G3MP2B3 calculations indicate a dHacid = 342 kcal/mol |
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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| 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-4974 |
| NIST MS number | 230099 |
UV/Visible spectrum
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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.
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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Download spectrum in JCAMP-DX format.
| Source | Laismann, 1973 |
|---|---|
| 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. 15978 |
| Instrument | Cary 14 |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics 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.
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]
Paul and Kebarle, 1989
Paul, G.; Kebarle, P.,
Electron Affinities of Cyclic Unsaturated Dicarbonyls: Maleic Anhydrides, Maleimides, and Cyclopentendione,
J. Am. Chem. Soc., 1989, 111, 2, 464, https://doi.org/10.1021/ja00184a009
. [all data]
Laismann, 1973
Laismann, Scharf ahd H.,
Z. Naturforsch., 1973, 28 b, 662. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
EA Electron affinity 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
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