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
Go To: Top, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), 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 | -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 |
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 |
Ion clustering 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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.
Clustering 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 |
Mass spectrum (electron ionization)
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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 | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118516 |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), 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]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy EA Electron affinity T Temperature ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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