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1,3-Cyclopentanedione

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Gas phase ion energetics 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:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

Ionization energy determinations

IE (eV) Method Reference Comment
9.46 ± 0.05PEHouk, Davis, et al., 1973LLK
9.53PEGleiter, Hofmann, et al., 1980Vertical value; LLK

De-protonation reactions

C5H5O2- + Hydrogen cation = 1,3-Cyclopentanedione

By formula: C5H5O2- + H+ = C5H6O2

Quantity Value Units Method Reference Comment
Deltar1395. ± 8.8kJ/molG+TSMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B
Quantity Value Units Method Reference Comment
Deltar1366. ± 8.4kJ/molIMREMishima, Matsuoka, et al., 2004gas phase; Calc: keto form of acid more stable.; B

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.

Houk, Davis, et al., 1973
Houk, K.N.; Davis, L.P.; Newkome, G.R.; Duke, R.E., Jr.; Nauman, R.V., Photoelectron spectroscopy of cyclic «beta»-diketones their enolone tautomers, J. Am. Chem. Soc., 1973, 95, 8364. [all data]

Gleiter, Hofmann, et al., 1980
Gleiter, R.; Hofmann, P.; Schang, P.; Sieber, A., The orbital sequence in cyclic 1,3-diketones, Tetrahedron, 1980, 36, 655. [all data]

Mishima, Matsuoka, et al., 2004
Mishima, M.; Matsuoka, M.; Lei, Y.X.; Rappoport, Z., Gas-phase acidities of disubstituted methanes and of enols of carboxamides substituted by electron-withdrawing groups, J. Org. Chem., 2004, 69, 18, 5947-5965, https://doi.org/10.1021/jo040196b . [all data]


Notes

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