Benzene, 1,2,4,5-tetrafluoro-
- Formula: C6H2F4
- Molecular weight: 150.0737
- IUPAC Standard InChIKey: SDXUIOOHCIQXRP-UHFFFAOYSA-N
- CAS Registry Number: 327-54-8
- 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: 1,2,4,5-Tetrafluorobenzene; 2,3,5,6-Tetrafluorobenzene
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, 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 | -646.8 ± 3.4 | kJ/mol | Ccr | Harrop and Head, 1978 |
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 evaluated as indicated in comments:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 9.33 ± 0.07 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 746.5 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 718.8 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.2 | PE | Maier and Thommen, 1981 | LLK |
9.349 ± 0.004 | EQ | Lias and Ausloos, 1978 | LLK |
9.39 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.36 | PE | Streets and Ceasar, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H2F3+ | 15.9 ± 0.1 | F | EI | Majer and Patrick, 1962 | RDSH |
De-protonation reactions
C6HF4- + =
By formula: C6HF4- + H+ = C6H2F4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1513. ± 8.8 | kJ/mol | G+TS | Buker, Nibbering, et al., 1997 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1478. ± 8.4 | kJ/mol | IMRE | Buker, Nibbering, et al., 1997 | gas phase; B |
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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
RCD - Robert C. Dunbar
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: C6H6+ + C6H2F4 = (C6H6+ • C6H2F4)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50.2 | kJ/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 110. | J/mol*K | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
By formula: Cr+ + C6H2F4 = (Cr+ • C6H2F4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 111. | kJ/mol | RAK | Ryzhov, 1999 | RCD |
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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Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.
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 | NIST Mass Spectrometry Data Center |
State | gas |
Instrument | HP-GC/MS/IRD |
UV/Visible spectrum
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina
Spectrum
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Additional Data
View image of digitized spectrum (can be printed in landscape orientation).
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Download spectrum in JCAMP-DX format.
Source | Hitchcock, Fischer, et al., 1987 |
---|---|
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. 1399 |
Instrument | n.i.g. |
Melting point | 4.5 |
Boiling point | 90.2 |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering 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.
Harrop and Head, 1978
Harrop, D.; Head, A.J.,
Thermodynamic properties of fluorine compounds. 18. Enthalpy of combustion of 1,2,4,5-tetrafluorobenzene,
J. Chem. Thermodyn., 1978, 10, 705-706. [all data]
Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G.,
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update,
J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018
. [all data]
Maier and Thommen, 1981
Maier, J.P.; Thommen, F.,
Fluorescence quantum yields and lifetimes of fluorobenzene cations in selected levels of their B and C states determined by photoelectron-photoion coincidence spectroscopy,
Chem. Phys., 1981, 57, 319. [all data]
Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J.,
eIonization energies of organic compounds by equilibrium measurements,
J. Am. Chem. Soc., 1978, 100, 6027. [all data]
Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C.,
The effect of fluorine on the electronic spectra and ionization potentials of molecules,
Proc. Roy. Soc. (London), 1960, A258, 459. [all data]
Streets and Ceasar, 1973
Streets, D.G.; Ceasar, G.P.,
Inductive mesomeric effects on the π orbitals of halobenzenes,
Mol. Phys., 1973, 26, 1037. [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]
Buker, Nibbering, et al., 1997
Buker, H.H.; Nibbering, N.M.M.; Espinosa, D.; Mongin, F.; Schlosser, M.,
Additivity of substituent effects in the fluoroarene series: Equilibrium acidity in the gas phase and deprotonation rates in ethereal solution,
Tetrahed. Lett., 1997, 38, 49, 8519-8522, https://doi.org/10.1016/S0040-4039(97)10303-3
. [all data]
Meot-Ner (Mautner), Hamlet, et al., 1978
Meot-Ner (Mautner), M.; Hamlet, P.; Hunter, E.P.; Field, F.H.,
Bonding Energies in Association Ions of Aromatic Molecules. Correlations with Ionization Energies,
J. Am. Chem. Soc., 1978, 100, 17, 5466, https://doi.org/10.1021/ja00485a034
. [all data]
Ryzhov, 1999
Ryzhov, V.,
Binding Energies of Chromium Cations with Fluorobenzenes from Radiative Association Kinetics,
Int. J. Mass Spectrom., 1999, 185/186/187, 913. [all data]
Hitchcock, Fischer, et al., 1987
Hitchcock, H.P.; Fischer, P.; Gedanken, A.; Robin, M.B.,
Antibonding α valence MOs in the inner-shell and outer-shell spectra of the fluorobenzenes,
J. Phys. Chem., 1987, 91, 531-540. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy 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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