Benzene, pentafluoro(trifluoromethyl)-
- Formula: C7F8
- Molecular weight: 236.0621
- 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
The 3d structure may be viewed using Java or Javascript. - Other names: Toluene, octafluoro-; (Trifluoromethyl)pentafluorobenzene; Octafluorotoluene; Perfluorotoluene; Pentafluoro(trifluoro-methyl)benzene
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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 as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -356.8 | kcal/mol | Semi | Stewart, 2004 | |
ΔfH°gas | -303.4 ± 1.9 | kcal/mol | Ccb | Krech, Price, et al., 1973 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -303.2 ± 1.8 kcal/mol; ALS |
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 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 | -313.4 ± 1.9 | kcal/mol | Ccb | Krech, Price, et al., 1973 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -313.2 ± 1.8 kcal/mol; ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 86.07 | cal/mol*K | N/A | Paukov, 1975 | DH |
S°liquid | 84.97 | cal/mol*K | N/A | Andon and Martin, 1974 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
63.67 | 298.15 | Paukov, 1975 | T = 13 to 300 K.; DH |
62.69 | 298.15 | Andon and Martin, 1974 | T = 10 to 315 K.; DH |
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
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
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 |
---|---|---|---|---|---|
Tboil | 376. to 378. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 377.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 207.62 | K | N/A | Paukov, 1975 | Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 207.69 | K | N/A | Andon and Martin, 1974, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 534.4 | K | N/A | Skripov and Muratov, 1977 | TRC |
Tc | 534.47 | K | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tc | 534.47 | K | N/A | Hales and Townsend, 1974 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 26.45 | atm | N/A | Skripov and Muratov, 1977 | Vis, pc by extrapolation of VP; TRC |
Pc | 26.70 | atm | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.04 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.338 | mol/l | N/A | Hales and Townsend, 1974 | Uncertainty assigned by TRC = 0.0023 mol/l; Liquid density determined by magnetically balanced float up to 490 K, see J.L.Hales, 1970-128. Critical D by equation due to Riedel.; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 9.68 ± 0.05 | kcal/mol | N/A | Dias, Gonçalves, et al., 2005 | Based on data from 288. to 334. K.; AC |
ΔvapH° | 9.66 | kcal/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 290. to 400. K. See also Basarová and Svoboda, 1991.; AC |
ΔvapH° | 9.95 ± 0.05 | kcal/mol | V | Krech, Price, et al., 1973 | ALS |
ΔvapH° | 9.94 ± 0.05 | kcal/mol | N/A | Krech, Price, et al., 1973 | Based on data from 285. to 334. K.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
9.56 | 306. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 291. to 378. K.; AC |
9.78 | 300. | A | Stephenson and Malanowski, 1987 | Based on data from 285. to 376. K.; AC |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.7679 | 207.62 | Paukov, 1975 | DH |
2.7462 | 207.69 | Andon and Martin, 1974 | DH |
2.746 | 207. | Domalski and Hearing, 1996 | AC |
Entropy of fusion
ΔfusS (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.22 | 207.69 | Andon and Martin, 1974 | DH |
Reaction 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 as indicated in comments:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.
Individual Reactions
By formula: F- + C7F8 = (F- • C7F8)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 33.6 ± 2.0 | kcal/mol | IMRE | Dillow and Kebarle, 1988 | gas phase; Anchored to C6F6..F- in Hiraoka, Mizuse, et al., 1987; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 20.1 | cal/mol*K | N/A | Dillow and Kebarle, 1988 | gas phase; switching reaction,Thermochemical ladder(C6F6), Entropy change calculated or estimated; Hiraoka, Mizuse, et al., 1987; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 25.1 ± 2.0 | kcal/mol | IMRE | Dillow and Kebarle, 1988 | gas phase; Anchored to C6F6..F- in Hiraoka, Mizuse, et al., 1987; B |
Free energy of reaction
ΔrG° (kcal/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
25.1 | 423. | PHPMS | Dillow and Kebarle, 1988 | gas phase; switching reaction,Thermochemical ladder(C6F6), Entropy change calculated or estimated; Hiraoka, Mizuse, et al., 1987; M |
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 |
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | Sadtler Research Labs Under US-EPA Contract |
State | gas |
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 | (editor), 1967 |
---|---|
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. 18960 |
Instrument | SFD-2 |
Boiling point | 104.0-105.0 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Notes
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]
PCR Inc., 1990
PCR Inc.,
Research Chemicals Catalog 1990-1991, PCR Inc., Gainesville, FL, 1990, 1. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Andon and Martin, 1974, 2
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. 1, 1974, 70, 605. [all data]
Skripov and Muratov, 1977
Skripov, V.P.; Muratov, G.N.,
The surface tensions of liquids and their interpretation by the method of thermodynamic similarity.,
Russ. J. Phys. Chem. (Engl. Transl.), 1977, 51, 806-8. [all data]
Ambrose, Broderick, et al., 1974
Ambrose, D.; Broderick, B.E.; Townsend, R.,
The Critical Temperatures and Pressures of Thirty Organic Compounds,
J. Appl. Chem. Biotechnol., 1974, 24, 359. [all data]
Hales and Townsend, 1974
Hales, J.L.; Townsend, R.,
Liquid Densities from 293 to 490 K of Eight Fluorinated Aromatic Comp.,
J. Chem. Thermodyn., 1974, 6, 111-6. [all data]
Dias, Gonçalves, et al., 2005
Dias, Ana M.A.; Gonçalves, Carla M.B.; Caço, Ana I.; Santos, Luís M.N.B.F.; Piñeiro, Manuel M.; Vega, Lourdes F.; Coutinho, João A.P.; Marrucho, Isabel M.,
Densities and Vapor Pressures of Highly Fluorinated Compounds,
J. Chem. Eng. Data, 2005, 50, 4, 1328-1333, https://doi.org/10.1021/je050056e
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav,
Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data,
Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I
. [all data]
Dykyj, Svoboda, et al., 1999
Dykyj, J.; Svoboda, J.; Wilhoit, R.C.; Frenkel, M.L.; Hall, K.R.,
Vapor Pressure of Chemicals: Part A. Vapor Pressure and Antoine Constants for Hydrocarbons and Sulfur, Selenium, Tellurium and Hydrogen Containing Organic Compounds, Springer, Berlin, 1999, 373. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Dillow and Kebarle, 1988
Dillow, G.W.; Kebarle, P.,
Fluoride Affinities of Perfluorobenzenes C6F5X. Meisenheimer Complexes in the Gas Phase and Solution,
J. Am. Chem. Soc., 1988, 110, 15, 4877, https://doi.org/10.1021/ja00223a001
. [all data]
Hiraoka, Mizuse, et al., 1987
Hiraoka, K.; Mizuse, S.; Yamabe, S.,
A Determination of the Stability and Structure of F-(C6H6) and F-(C6F6) Clusters,
J. Chem. Phys., 1987, 86, 7, 4102, https://doi.org/10.1063/1.451920
. [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]
(editor), 1967
(editor), Koptyug V.A.,
Atlas of Spectra of Aromatic and Heterocyclic Compounds, 1967, 1, 23. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity Pc Critical pressure S°liquid Entropy of liquid at standard conditions T Temperature Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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