2,4-Pentanedione, 1,1,1-trifluoro-
- Formula: C5H5F3O2
- Molecular weight: 154.0872
- IUPAC Standard InChI: InChI=1S/C5H5F3O2/c1-3(9)2-4(10)5(6,7)8/h2H2,1H3
- IUPAC Standard InChIKey: SHXHPUAKLCCLDV-UHFFFAOYSA-N
- CAS Registry Number: 367-57-7
- 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: (Trifluoroacetyl)acetone; 1,1,1-Trifluoro-2,4-pentanedione; 1,1,1-Trifluoroacetylacetone; CF3COH=CHCOCH3; 1,1,1-Trifluoro-2,4-pentadione; Acetyl trifluoroacetone; 1,1,1-trifluoropentane-2,4-dione
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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:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 9.47 | EI | Orlov, Rashkes, et al., 1988 | LL |
| 9.5 | PE | Evans, Hamnett, et al., 1972 | LLK |
| 9.8 ± 0.1 | EI | Reichert, Bancroft, et al., 1970 | RDSH |
| 9.92 ± 0.07 | PE | Evans, Hamnett, et al., 1972 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C2H3O+ | 10.20 | C3H2F3O | EI | Orlov, Rashkes, et al., 1988 | LL |
| C4H2O2F3+ | 11.7 ± 0.1 | CH3 | EI | Reichert, Bancroft, et al., 1970 | RDSH |
| C4H5O2+ | 10.6 ± 0.2 | CF3 | EI | Reichert, Bancroft, et al., 1970 | RDSH |
De-protonation reactions
C5H4F3O2- + =
By formula: C5H4F3O2- + H+ = C5H5F3O2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1374. ± 12. | kJ/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrH° | 1374. ± 17. | kJ/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1347. ± 8.4 | kJ/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
| ΔrG° | 1348. ± 8.4 | kJ/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
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.
Orlov, Rashkes, et al., 1988
Orlov, V.M.; Rashkes, Y.V.; Siretskaya, T.V.; Takhistov, V.V.,
Thermochemical description of tutomeric transformations in ionized 1,3-diketones,
J. Gen. Chem. USSR, 1988, 58, 374. [all data]
Evans, Hamnett, et al., 1972
Evans, S.; Hamnett, A.; Orchard, A.F.; Lloyd, D.R.,
Study of the metal-oxygen bond in simple tris-chelate complexes by He(I) photoelectron spectroscopy,
Faraday Discuss. Chem. Soc., 1972, 54, 227. [all data]
Reichert, Bancroft, et al., 1970
Reichert, C.; Bancroft, G.M.; Westmore, J.B.,
Mass spectral studies of metal chelates. V. Mass spectra and appearance potentials of some fluorine-substituted acetylacetonates,
Can. J. Chem., 1970, 48, 1362. [all data]
Fujio, McIver, et al., 1981
Fujio, M.; McIver, R.T., Jr.; Taft, R.W.,
Effects on the acidities of phenols from specific substituent-solvent interactions. Inherent substituent parameters from gas phase acidities,
J. Am. Chem. Soc., 1981, 103, 4017. [all data]
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]
Notes
Go To: Top, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy 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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