p-Benzoquinone, 2,3,5,6-tetrafluoro-
- Formula: C6F4O2
- Molecular weight: 180.0566
- IUPAC Standard InChI: InChI=1S/C6F4O2/c7-1-2(8)6(12)4(10)3(9)5(1)11
- IUPAC Standard InChIKey: JKLYZOGJWVAIQS-UHFFFAOYSA-N
- CAS Registry Number: 527-21-9
- 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: p-Fluoranil; 2,5-Cyclohexadiene-1,4-dione, 2,3,5,6-tetrafluoro-; Fluoranil; Fluoroanil; Tetrafluoro-p-benzoquinone; Tetrafluoro-1,4-benzoquinone; Tetrafluoroquinone; 2,3,5,6-Tetrafluoro-p-benzoquinone; Perfluoro-p-benzoquinone; p-Benzoquinone, tetrafluoro-; 2,3,5,6-Tetrafluoro-1,4-benzoquinone; Tetrafluorobenzoquinone; NSC 264881; Tetrafluoro-p-quinone
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Reaction thermochemistry data
Go To: Top, 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:
B - John E. Bartmess
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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Individual Reactions
+
= (
•
)
By formula: Cl- + C6F4O2 = (Cl- • C6F4O2)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 27.0 ± 1.0 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B,M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrS° | 22.7 | cal/mol*K | PHPMS | Chowdhury and Kebarle, 1986 | gas phase; M |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 20.2 ± 1.6 | kcal/mol | TDAs | Chowdhury and Kebarle, 1986 | gas phase; B |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry 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:
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
B - John E. Bartmess
Electron affinity determinations
| EA (eV) | Method | Reference | Comment |
|---|---|---|---|
| 2.70 ± 0.10 | IMRE | Heinis, Chowdhury, et al., 1988 | ΔGea(423 K) = -60.9 kcal/mol; ΔSea (estimated) = -3.5 eu.; B |
| 2.446 ± 0.048 | IMRE | Fukuda and McIver, 1985 | ΔGea(355 K) = -55.2 kcal/mol; ΔSea =-3.5, est. from data in Heinis, Chowdhury, et al., 1988; B |
| 2.92 ± 0.20 | NBIE | Cooper, Frey, et al., 1978 | B |
| 2.26794 | SI | Page and Goode, 1969 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.7 | PE | Asbrink, Svensson, et al., 1981 | LLK |
| 10.96 ± 0.05 | PE | Dougherty and McGlynn, 1977 | Vertical value; LLK |
References
Go To: Top, 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.
Chowdhury and Kebarle, 1986
Chowdhury, S.; Kebarle, P.,
Role of Binding Energies in A-.B and A.B- Complexes in the Kinetics of Gas Phase Electron Transfer Reactions:A- + B = A + B- Involving Perfluoro Compounds: SF6, C6F11CF3,
J. Chem. Phys., 1986, 85, 9, 4989, https://doi.org/10.1063/1.451687
. [all data]
Heinis, Chowdhury, et al., 1988
Heinis, T.; Chowdhury, S.; Scott, S.L.; Kebarle, P.,
Electron Affinities of Benzo-, Naphtho-, and Anthraquinones Determined from Gas-Phase Equilibria Measurements,
J. Am. Chem. Soc., 1988, 110, 2, 400, https://doi.org/10.1021/ja00210a015
. [all data]
Fukuda and McIver, 1985
Fukuda, E.K.; McIver, R.T., Jr.,
Relative electron affinities of substituted benzophenones, nitrobenzenes, and quinones. [Anchored to EA(SO2) from 74CEL/BEN],
J. Am. Chem. Soc., 1985, 107, 2291. [all data]
Cooper, Frey, et al., 1978
Cooper, C.D.; Frey, W.F.; Compton, R.N.,
Negative ion properties of fluoranil, chloranil, and bromanil: Electron affinities,
J. Chem. Phys., 1978, 69, 2367. [all data]
Page and Goode, 1969
Page, F.M.; Goode, G.C.,
Negative Ions and the Magnetron., Wiley, NY, 1969. [all data]
Asbrink, Svensson, et al., 1981
Asbrink, L.; Svensson, A.; Von Niessen, W.; Bieri, G.,
30.4 nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1981, 24, 293. [all data]
Dougherty and McGlynn, 1977
Dougherty, D.; McGlynn, S.P.,
Photoelectron spectroscopy of carbonyls. 1,4-Benzoquinones,
J. Am. Chem. Soc., 1977, 99, 3234. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
EA Electron affinity 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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