Benzene, pentafluoro(trifluoromethyl)-
- Formula: C7F8
- Molecular weight: 236.0621
- IUPAC Standard InChI: InChI=1S/C7F8/c8-2-1(7(13,14)15)3(9)5(11)6(12)4(2)10
- IUPAC Standard InChIKey: USPWUOFNOTUBAD-UHFFFAOYSA-N
- CAS Registry Number: 434-64-0
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
View 3d structure (requires JavaScript / HTML 5) - Other names: Toluene, octafluoro-; (Trifluoromethyl)pentafluorobenzene; Octafluorotoluene; Perfluorotoluene; Pentafluoro(trifluoro-methyl)benzene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Gas phase ion energetics data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | -1493. | kJ/mol | Semi | Stewart, 2004 | |
| ΔfH°gas | -1269.4 ± 7.8 | kJ/mol | Ccb | Krech, Price, et al., 1973 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -1269. ± 7.5 kJ/mol; ALS |
Condensed phase thermochemistry data
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, 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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | -1311.1 ± 7.8 | kJ/mol | Ccb | Krech, Price, et al., 1973 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -1310.2 ± 7.5 kJ/mol; ALS |
| Quantity | Value | Units | Method | Reference | Comment |
| S°liquid | 360.1 | J/mol*K | N/A | Paukov, 1975 | DH |
| S°liquid | 355.5 | J/mol*K | N/A | Andon and Martin, 1974 | DH |
Constant pressure heat capacity of liquid
| Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 266.4 | 298.15 | Paukov, 1975 | T = 13 to 300 K.; DH |
| 262.3 | 298.15 | Andon and Martin, 1974 | T = 10 to 315 K.; DH |
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:
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
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 0.86 ± 0.11 | IMRE | Dillow and Kebarle, 1989 | ΔGea(423 K) = -21.3±1.0 kcal/mol , assumed entropy = 3.5 eu. The literature exptl HOF(C6F5CF3)=-303.2 (73KRE/KLI) is clearly wrong; B |
| >1.70 ± 0.30 | Endo | Lifshitz, Tiernan, et al., 1973 | B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| ~10.2 | EI | Holman, Kiplinger, et al., 1993 | LL |
| 10.4 ± 0.1 | EI | Majer and Patrick, 1962 | RDSH |
| 10.54 | PE | Furin, Zibarev, et al., 1989 | Vertical value; LL |
| 9.9 | PE | Maier, Marthaler, et al., 1980 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C7F7+ | 13.6 | F | EI | Holman, Kiplinger, et al., 1993 | LL |
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.
Stewart, 2004
Stewart, J.J.P.,
Comparison of the accuracy of semiempirical and some DFT methods for predicting heats of formation,
J. Mol. Model, 2004, 10, 1, 6-10, https://doi.org/10.1007/s00894-003-0157-6
. [all data]
Krech, Price, et al., 1973
Krech, M.J.; Price, S.J.W.; Yared, W.F.,
Determination of the heat of formation of octafluorotoluene and calculation of D[C6F5-F] - D[C6F5-CF3],
Can. J. Chem., 1973, 51, 3662-3664. [all data]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Paukov, 1975
Paukov, I.E.,
Thermodynamic properties of octafluorotoluene in the temperature range 13 to 300 K,
Zhur. Fiz. Khim., 1975, 49, 265. [all data]
Andon and Martin, 1974
Andon, R.J.L.; Martin, J.F.,
Thermodynamic properties of fluorine compounds. Part 14. Low-temperature heat capacity and entropy of octafluorotoluene,
J. Chem. Soc. Faraday Trans., 1974, I 70, 605-608. [all data]
Dillow and Kebarle, 1989
Dillow, G.W.; Kebarle, P.,
Substituent Effects on the Electron Affinities of Perfluorobenzenes C6F5X,
J. Am. Chem. Soc., 1989, 111, 15, 5592, https://doi.org/10.1021/ja00197a014
. [all data]
Lifshitz, Tiernan, et al., 1973
Lifshitz, C.; Tiernan, T.O.; Hughes, B.M.,
Electron affinities from endothermic negative-ion charge transfer reactions. IV. SF6, selected fluorocarbons, and other polyatomic molecules,
J. Chem. Phys., 1973, 59, 3182. [all data]
Holman, Kiplinger, et al., 1993
Holman, R.W.; Kiplinger, J.P.; Tuinman, A.A.; Bloor, J.E.; Bartmess, J.E.,
Structures of gas-phase C7F7+ ions,
J. Am. Soc. Mass Spectrom., 1993, 4, 813. [all data]
Majer and Patrick, 1962
Majer, J.R.; Patrick, C.R.,
Electron impact on some halogenated aromatic compounds,
J. Chem. Soc. Faraday Trans., 1962, 58, 17. [all data]
Furin, Zibarev, et al., 1989
Furin, G.G.; Zibarev, A.V.; Sultanov, A.Sh.; Furlei, I.I.,
Order and structure of the outer valence Mo's of some derivatives of pentafluorobenzene,
Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 4, 772. [all data]
Maier, Marthaler, et al., 1980
Maier, J.P.; Marthaler, O.; Mohraz, M.,
Decay of some substituted benzene cations in the B states in the gaseous phase,
J. Chim. Phys., 1980, 77, 661. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity S°liquid Entropy 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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