2,4-Pentanedione, 1,1,1-trifluoro-
- Formula: C5H5F3O2
- Molecular weight: 154.0872
- 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 thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -239.79 ± 0.79 | kcal/mol | Ccr | Erastov, Kolesov, et al., 1984 | Hf-gas-(enol) |
ΔfH°gas | -237.4 ± 0.81 | kcal/mol | Ccr | Erastov, Kolesov, et al., 1984 | Hf-gas-(keto) |
Condensed phase thermochemistry 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -248.61 ± 0.79 | kcal/mol | Ccr | Erastov, Kolesov, et al., 1984 | Hf-gas-(enol) |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -521.01 ± 0.62 | kcal/mol | Ccr | Erastov, Kolesov, et al., 1984 | Hf-gas-(enol) |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 379.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 380. | K | N/A | Farchan Laboratories, 1990 | BS |
Tboil | 380. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 380.2 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.908 | kcal/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 8.89 ± 0.05 | kcal/mol | N/A | Ribeiro da Silva, Gonçalves, et al., 1997 | See also Irving and da Silva, 1975 and Ribeiro da Silva and Irving, 1978.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Reference |
---|---|---|
7.459 | 380.2 | Majer and Svoboda, 1985 |
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
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° | 328.3 ± 2.9 | kcal/mol | G+TS | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrH° | 328.5 ± 4.1 | kcal/mol | G+TS | Cumming and Kebarle, 1978 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 322.0 ± 2.0 | kcal/mol | IMRE | Fujio, McIver, et al., 1981 | gas phase; value altered from reference due to change in acidity scale; B |
ΔrG° | 322.1 ± 2.0 | kcal/mol | IMRE | Cumming and Kebarle, 1978 | gas phase; B |
IR Spectrum
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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: Coblentz Society, Inc.
Condensed Phase Spectrum
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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.
Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
Additional Data
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Owner | COBLENTZ SOCIETY Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | STANDARD OIL OF OHIO |
Source reference | COBLENTZ NO. 857 |
Date | 1960 |
Name(s) | 1,1,1-trifluoro-2,4-pentanedione |
State | LIQUID |
Instrument | Not specified, most likely a grating spectrometer. |
Path length | 0.00204 CM |
Resolution | 4 |
Sampling procedure | TRANSMISSION |
Data processing | DIGITIZED BY NIST FROM HARD COPY |
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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Due to licensing restrictions, this spectrum cannot be downloaded.
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-IW-5622 |
NIST MS number | 230278 |
UV/Visible spectrum
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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
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Source | Larsen and Leddy, 1953 |
---|---|
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. 12104 |
Instrument | Cary Model 11 |
Melting point | 128 |
Boiling point | 107 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, 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.
Erastov, Kolesov, et al., 1984
Erastov, P.A.; Kolesov, V.P.; Igumenov, I.K.,
Standard enthalpies of formation of some fluorinated β-diketones,
Russ. J. Phys. Chem. (Engl. Transl.), 1984, 58, 1311-1313. [all data]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]
Farchan Laboratories, 1990
Farchan Laboratories,
Research Chemicals Catalog, Farchan Laboratories, Gainesville, FL, 1990, 91. [all data]
PCR Inc., 1990
PCR Inc.,
Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Ribeiro da Silva, Gonçalves, et al., 1997
Ribeiro da Silva, Manuel A.V.; Gonçalves, J.M.; Pilcher, G.,
Standard molar enthalpies of formation of nine fluorinated β-diketones by rotating bomb calorimetry,
The Journal of Chemical Thermodynamics, 1997, 29, 3, 253-260, https://doi.org/10.1006/jcht.1996.0143
. [all data]
Irving and da Silva, 1975
Irving, Roger J.; da Silva, Manuel A.V. Ribeiro,
Enthalpies of vaporization of some ?-diketones,
J. Chem. Soc., Dalton Trans., 1975, 9, 798, https://doi.org/10.1039/dt9750000798
. [all data]
Ribeiro da Silva and Irving, 1978
Ribeiro da Silva, M.A.V.; Irving, R.G.,
Rev. Port. Quim., 1978, 20, 36. [all data]
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]
Larsen and Leddy, 1953
Larsen, E.M.; Leddy, J.,
J. Am. Chem. Soc., 1953, 75, 5107. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy Tboil Boiling point ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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