Benzene, pentafluoromethyl-
- Formula: C7H3F5
- Molecular weight: 182.0907
- IUPAC Standard InChIKey: SXPRVMIZFRCAGC-UHFFFAOYSA-N
- CAS Registry Number: 771-56-2
- 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, 2,3,4,5,6-pentafluoro-; Methyl pentafluorobenzene; 2,3,4,5,6-Pentafluorotoluene; 2,3,4,5,6-Pentafluoro-1-methylbenzene; Pentafluoromethylbenzene; Pentafluorotoluene
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -843.3 ± 1.5 | kJ/mol | Ccr | Cox, Gundry, et al., 1969 |
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 | -884.2 ± 1.5 | kJ/mol | Ccr | Cox, Gundry, et al., 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -3194.4 ± 1.5 | kJ/mol | Ccr | Cox, Gundry, et al., 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 310.87 | J/mol*K | N/A | Paukov, 1971 | DH |
S°liquid | 306.4 | J/mol*K | N/A | Counsell, Hales, et al., 1968 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
231.12 | 298.15 | Paukov, 1971 | T = 12 to 305 K. Data deposited VINITI, No. 2538-71, 20 Jan 1971.; DH |
225.8 | 298.15 | Counsell, Hales, et al., 1968 | T = 10 to 376 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 | 390. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 390.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 390.6 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 243.7 | K | N/A | Paukov, 1971, 2 | Uncertainty assigned by TRC = 0.2 K; TRC |
Ttriple | 243.35 | K | N/A | Counsell, Hales, et al., 1968, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 548.6 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 566.52 | K | N/A | Hales and Townsend, 1974 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 2.600 | mol/l | N/A | Hales and Townsend, 1974 | Uncertainty assigned by TRC = 0.0026 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° | 41.13 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 41.2 | kJ/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 310. to 410. K. See also Basarová and Svoboda, 1991.; AC |
ΔvapH° | 40.9 ± 0.4 | kJ/mol | V | Cox, Gundry, et al., 1969 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
34.75 | 390.6 | N/A | Majer and Svoboda, 1985 | |
36.1 | 418. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 403. to 523. K.; AC |
34.9 | 508. | N/A | Dykyj, Svoboda, et al., 1999 | Based on data from 493. to 564. K.; AC |
39.9 | 327. | A | Stephenson and Malanowski, 1987 | Based on data from 312. to 416. K. See also Ambrose, 1968, Kkykj and Repas, 1973, and Dykyj, Svoboda, et al., 1999.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
349. to 391. | 58.64 | 0.2674 | 548.6 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
312.31 to 411.37 | 4.2170 | 1396.766 | -58.974 | Ambrose, 1968, 2 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
13.280 | 243.7 | Paukov, 1971 | Transition 0.3 K below mp, H is sum of transition and fusion.; DH |
13.28 | 243.7 | Domalski and Hearing, 1996 | See also Counsell, Hales, et al., 1968, 2.; AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
54.49 | 243.7 | Paukov, 1971 | Transition; DH |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
0.2103 | 70.3 | crystaline, II | crystaline, I | Counsell, Hales, et al., 1968 | DH |
12.990 | 243.35 | crystaline, II | crystaline, I | Counsell, Hales, et al., 1968 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
2.94 | 70.3 | crystaline, II | crystaline, I | Counsell, Hales, et al., 1968 | DH |
53.38 | 243.35 | crystaline, II | crystaline, I | Counsell, Hales, et al., 1968 | 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:
B - John E. Bartmess
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 |
---|---|---|---|
9.4 | PE | Maier, Marthaler, et al., 1980 | LLK |
9.6 ± 0.1 | EI | Majer and Patrick, 1962 | RDSH |
9.4 | PE | Maier, Marthaler, et al., 1980 | Vertical value; LLK |
9.81 | PE | Trudell and Price, 1979 | Vertical value; LLK |
De-protonation reactions
C7H2F5- + =
By formula: C7H2F5- + H+ = C7H3F5
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1512. ± 8.8 | kJ/mol | G+TS | Koppel, Taft, et al., 1994 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1484. ± 8.4 | kJ/mol | IMRE | Koppel, Taft, et al., 1994 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, 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.
Cox, Gundry, et al., 1969
Cox, J.D.; Gundry, H.A.; Harrop, D.; Head, A.J.,
Thermodynamic properties of fluorine compounds. 9. Enthalpies of formation of some compounds containing the pentafluorophenyl group,
J. Chem. Thermodyn., 1969, 1, 77-87. [all data]
Paukov, 1971
Paukov, I.E.,
Low-temperature heat capacity, phase transition, absolute entropy, and enthalpy of pentafluorotoluene,
Zhur. Fiz. Khim., 1971, 45, 1297-1298. [all data]
Counsell, Hales, et al., 1968
Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of fluorine compounds. Part VIII. The heat capacity and entropy of 2,3,4,5,6-pentafluorotoluene,
J. Chem. Soc. A, 1968, 2994-2996. [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]
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]
Paukov, 1971, 2
Paukov, I.E.,
Low-temperature heat capacity, phase transition, absolute entropy, and ethalpy of pentafluorotoluene,
Zh, Fiz. Khim., 1971, 45, 1297-8. [all data]
Counsell, Hales, et al., 1968, 2
Counsell, J.F.; Hales, J.L.; Lees, E.B.; Martin, J.F.,
Thermodynamic properties of fluorine compounds. Part VIII. The heat capacity and entropy of 2,3,4,5,6-pentafluorotoluene,
J. Chem. Soc., A, 1968, 2994, https://doi.org/10.1039/j19680002994
. [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]
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]
Ambrose, 1968
Ambrose, D.,
Thermodynamic properties of fluorine compounds. Part V. Vapour pressures of pentafluorobenzene, chloropentafluorobenzene, 2,3,4,5,6-pentafluorotoluene, and pentafluorophenol,
J. Chem. Soc., A, 1968, 1381, https://doi.org/10.1039/j19680001381
. [all data]
Kkykj and Repas, 1973
Kkykj, J.; Repas, M.,
Petrochemia, 1973, 13, 179. [all data]
Ambrose, 1968, 2
Ambrose, D.,
Thermodynamic Properties of Fluorine Compounds. Part V. Vapour Pressures of Pentafluorobenzene, Chloropentafluorobenzene, 2,3,4,5,6-Pentafluorotoluene, and Pentafluorophenol,
J. Chem. Soc. A:, 1968, 1381-1383, https://doi.org/10.1039/j19680001381
. [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]
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]
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]
Trudell and Price, 1979
Trudell, B.C.; Price, S.J.W.,
The ultraviolet photoelectron spectra of C6F5X compounds, X=(F, Cl, Br, I, H, CH3),
Can. J. Chem., 1979, 57, 2256. [all data]
Koppel, Taft, et al., 1994
Koppel, I.A.; Taft, R.W.; Anvia, F.; Zhu, S.Z.; Hu, L.Q.; Sung, K.S.; Desmarteau, D.D.; Yagupolskii, L.M.,
The Gas-Phase Acidities of Very Strong Neutral Bronsted Acids,
J. Am. Chem. Soc., 1994, 116, 7, 3047, https://doi.org/10.1021/ja00086a038
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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 ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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