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
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Other data available:
- Mass spectrum (electron ionization)
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Gas phase ion energetics data

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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

Gas Chromatography

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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	SPB-5	884.	Deport, Ratel, et al., 2006	60. m/0.32 mm/1. μm, He, 40. C @ 5. min, 3. K/min, 230. C @ 5. min
Capillary	BPX-5	911.	Ames, Guy, et al., 2001	50. m/0.32 mm/0.25 μm, He, 60. C @ 5. min, 4. K/min, 250. C @ 10. min

Van Den Dool and Kratz RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	CP-Wax 52CB	1576.	Mahadevan and Farmer, 2006	60. C @ 5. min, 4. K/min, 220. C @ 30. min; Column length: 50. m; Column diameter: 0.32 mm

Van Den Dool and Kratz RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	Supelcowax-10	1605.	Bianchi, Careri, et al., 2007	30. m/0.25 mm/0.25 μm, He; Program: 35C(8min) => 4C/min => 60C => 6C/min => 160C => 20C/min => 200C(1min)

Normal alkane RI, non-polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	HP-5 MS	880.	Kim and Chung, 2009	30. m/0.25 mm/0.25 μm, Helium, 35. C @ 5. min, 2. K/min, 195. C @ 30. min
Capillary	DB-1	846.	Tai and Ho, 1998	60. m/0.32 mm/1.0 μm, He, 2. K/min; T_start: 40. C; T_end: 280. C

Normal alkane RI, polar column, temperature ramp

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1535.	Guo, Wu, et al., 2008	30. m/0.25 mm/0.25 μm, Helium, 60. C @ 2. min, 10. K/min, 250. C @ 10. min
Capillary	Carbowax 20M	1548.	Kawakami and Kobayashi, 1991	He, 60. C @ 4. min, 2. K/min; Column length: 50. m; Column diameter: 0.25 mm; T_end: 180. C

Normal alkane RI, polar column, custom temperature program

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Column type	Active phase	I	Reference	Comment
Capillary	DB-Wax	1573.	Gonzalez-Rios, Suarez-Quiroz, et al., 2007	30. m/0.25 mm/0.25 μm, Hydrogen; Program: 44 0C 3 0C/min -> 170 0C 8 0C/min -> 250 0C

References

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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]

Deport, Ratel, et al., 2006
Deport, C.; Ratel, J.; Berdagué, J.-L.; Engel, E., Comprehensive combinatory standard correction: A calibration method for handling instrumental drifts of gas chromatography-mass spectrometry systems, J. Chromatogr. A, 2006, 1116, 1-2, 248-258, https://doi.org/10.1016/j.chroma.2006.03.092 . [all data]

Ames, Guy, et al., 2001
Ames, J.M.; Guy, R.C.E.; Kipping, G.J., Effect of pH, temperature, and moisture on the formation of volatile compounds in glycine/glucose model systems, J. Agric. Food Chem., 2001, 49, 9, 4315-4323, https://doi.org/10.1021/jf010198m . [all data]

Mahadevan and Farmer, 2006
Mahadevan, K.; Farmer, L., Key Odor Impact Compounds in Three Yeast Extract Pastes, J. Agric. Food Chem., 2006, 54, 19, 7242-7250, https://doi.org/10.1021/jf061102x . [all data]

Bianchi, Careri, et al., 2007
Bianchi, F.; Careri, M.; Mangia, A.; Musci, M., Retention indices in the analysis of food aroma volatile compounds in temperature-programmed gas chromatography: Database creation and evaluation of precision and robustness, J. Sep. Sci., 2007, 39, 4, 563-572, https://doi.org/10.1002/jssc.200600393 . [all data]

Kim and Chung, 2009
Kim, J.-S.; Chung, H.Y., GC-MS analysis of the volatile components in dried boxthorn (Lycium chimensis) Fruit, J. Korean Soc. Appl. Biol. Chem., 2009, 52, 5, 516-524, https://doi.org/10.3839/jksabc.2009.088 . [all data]

Tai and Ho, 1998
Tai, C.-Y.; Ho, C.-T., Influence of glutathione oxidation and pH on thermal formation of Maillard-type volatile compounds, J. Agric. Food Chem., 1998, 46, 6, 2260-2265, https://doi.org/10.1021/jf971111t . [all data]

Guo, Wu, et al., 2008
Guo, L.; Wu, J.-Z.; Han, T.; Cao, T.; Rahman, K.; Qin, L.-P., Chemical composition, antifungal and antitumor properties of ether extracts of Scapania verrucosa Heeg. and its endophytic fungus Chaetomium fusiforme, Molecules, 2008, 13, 9, 2114-2125, https://doi.org/10.3390/molecules13092114 . [all data]

Kawakami and Kobayashi, 1991
Kawakami, M.; Kobayashi, A., Volatitle constituents of greem mate and roasted mate, J. Agric. Food Chem., 1991, 39, 7, 1275-1279, https://doi.org/10.1021/jf00007a016 . [all data]

Gonzalez-Rios, Suarez-Quiroz, et al., 2007
Gonzalez-Rios, O.; Suarez-Quiroz, M.L.; Boulanger, R.; Barel, M.; Guyot, B.; Guiraud, J.-P.; Schorr-Galindo, S., Impact of ecological post-harvest processing of coffee aroma: II Roasted coffee., J. Food Composition Analysis, 2007, 20, 3-4, 297-307, https://doi.org/10.1016/j.jfca.2006.12.004 . [all data]

Notes

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Symbols used in this document:

AE Appearance energy

EA Electron affinity
Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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