4-Cyclopentene-1,3-dione
- Formula: C5H4O2
- Molecular weight: 96.0841
- IUPAC Standard InChI: InChI=1S/C5H4O2/c6-4-1-2-5(7)3-4/h1-2H,3H2
- IUPAC Standard InChIKey: MCFZBCCYOPSZLG-UHFFFAOYSA-N
- CAS Registry Number: 930-60-9
- 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-Cyclopentene-1,4-dione; 2-Cyclopenten-1,4-dione; 4-Cyclopenten-1,3-dione; Cyclopent-2-en-1,4-dione; Cyclopent-2-ene-1,4-dione; cyclopenten-1,4-dione; cyclopent-4-ene-1,3-dione
- Permanent link for this species. Use this link for bookmarking this species for future reference.
- Information on this page:
- Other data available:
- Options:
Gas phase ion energetics data
Go To: Top, 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:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 1.14 ± 0.13 | IMRE | Paul and Kebarle, 1989 | ΔGea(423 K) = -25.8±1 kcal/mol, ΔS(est) = -1±3 eu; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.6 | PE | Gleiter, Dobler, et al., 1982 | LBLHLM |
| 9.8 | PE | Gleiter, Dobler, et al., 1982 | Vertical value; LBLHLM |
| 10.25 | PE | Bain and Frost, 1973 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C4H4O+ | 10.88 | CO | EI | Burgers, Holmes, et al., 1982 | LBLHLM |
References
Go To: Top, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Gleiter, Dobler, et al., 1982
Gleiter, R.; Dobler, W.; Eckert-Maksic, M.,
The electronic structure of o-tropoquinone, p-tropoquinone, and cyclopentene-1,2,3-trione - PE spectroscopic investigations,
Nouv. J. Chim., 1982, 6, 123. [all data]
Bain and Frost, 1973
Bain, A.D.; Frost, D.C.,
Studies of the carbonyl group in some five-membered ring compounds by photoelectron spectroscopy,
Can. J. Chem., 1973, 51, 1245. [all data]
Burgers, Holmes, et al., 1982
Burgers, P.C.; Holmes, J.L.; Lossing, F.P.; Mommers, A.A.; Povel, F.R.; Terlouw, J.K.,
Isomeric and tautomeric [C4H4O]+ ions. Their thermochemistry and collisionally induced fragmentation characteristics,
Can. J. Chem., 1982, 60, 2246. [all data]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy EA Electron affinity - 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.