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
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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 | -201.6 ± 0.36 | kcal/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 | -211.3 ± 0.36 | kcal/mol | Ccr | Cox, Gundry, et al., 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -763.48 ± 0.36 | kcal/mol | Ccr | Cox, Gundry, et al., 1969 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 74.300 | cal/mol*K | N/A | Paukov, 1971 | DH |
S°liquid | 73.23 | cal/mol*K | N/A | Counsell, Hales, et al., 1968 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
55.239 | 298.15 | Paukov, 1971 | T = 12 to 305 K. Data deposited VINITI, No. 2538-71, 20 Jan 1971.; DH |
53.97 | 298.15 | Counsell, Hales, et al., 1968 | T = 10 to 376 K.; 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 by: John E. Bartmess
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
C7H2F5- + =
By formula: C7H2F5- + H+ = C7H3F5
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 361.3 ± 2.1 | kcal/mol | G+TS | Koppel, Taft, et al., 1994 | gas phase |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 354.7 ± 2.0 | kcal/mol | IMRE | Koppel, Taft, et al., 1994 | gas phase |
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° | 361.3 ± 2.1 | kcal/mol | G+TS | Koppel, Taft, et al., 1994 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 354.7 ± 2.0 | kcal/mol | IMRE | Koppel, Taft, et al., 1994 | gas phase; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry 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 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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