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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Condensed phase thermochemistry data
Go To: Top, Phase change data, Gas phase ion energetics 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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -683.8 ± 3.2 | kJ/mol | Ccr | Harrop and Head, 1978 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2679.0 ± 1.7 | kJ/mol | Ccr | Harrop and Head, 1978 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
S°liquid | 250.4 | J/mol*K | N/A | Andon and Martin, 1973 | DH |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
192.2 | 298.15 | Andon and Martin, 1973 | T = 10 to 350 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 | 363. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 362.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 277.03 | K | N/A | Andon and Martin, 1973, 2 | Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 543.35 | K | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.2 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 38.01 | bar | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.06 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 37.2 | kJ/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 290. to 390. K. See also Basarová and Svoboda, 1991.; AC |
ΔvapH° | 37.11 | kJ/mol | V | Findlay, 1969 | ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
33.1 | 405. | A | Stephenson and Malanowski, 1987 | Based on data from 390. to 488. K.; AC |
32.6 | 503. | A | Stephenson and Malanowski, 1987 | Based on data from 488. to 543. K.; AC |
36.8 | 308. | A | Stephenson and Malanowski, 1987 | Based on data from 293. to 390. K. See also Ambrose, Ellender, et al., 1975 and Boublik, Fried, et al., 1984.; AC |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
15.050 | 277.03 | Andon and Martin, 1973 | DH |
15.05 | 277. | Andon and Martin, 1973, 2 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
54.33 | 277.03 | Andon and Martin, 1973 | DH |
Gas phase ion energetics data
Go To: Top, Condensed phase thermochemistry data, Phase change 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 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 |
Mass spectrum (electron ionization)
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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Spectrum
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Additional Data
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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 | 118783 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics 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.
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]
Andon and Martin, 1973
Andon, R.J.L.; Martin, J.F.,
Thermodynamic properties of fluorine compounds. Part 11. Low-temperature heat capacities of the three tetrafluorobenzenes,
J. Chem. Soc. Faraday Trans., 1973, I 69, 761-770. [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]
Andon and Martin, 1973, 2
Andon, R.J.L.; Martin, J.F.,
Thermodynamic properties of fluorine compounds. Part 11.---Low-temperature heat capacities of the three tetrafluorobenzenes,
J. Chem. Soc., Faraday Trans. 1, 1973, 69, 0, 761, https://doi.org/10.1039/f19736900761
. [all data]
Ambrose, Broderick, et al., 1974
Ambrose, D.; Broderick, B.E.; Townsend, R.,
The Critical Temperatures and Pressures of Thirty Organic Compounds,
J. Appl. Chem. Biotechnol., 1974, 24, 359. [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]
Findlay, 1969
Findlay, T.J.V.,
Vapor pressures of fluorobenzenes from 5° to 50°C,
J. Chem. Eng. Data, 1969, 14, 229. [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, Ellender, et al., 1975
Ambrose, D.; Ellender, J.H.; Sprake, C.H.S.; Townsend, R.,
Thermodynamic properties of fluorine compounds. Part 15.---Vapour pressures of the three tetrafluorobenzenes and 1,3,5-trichloro-2,4,6-trifluorobenzene,
J. Chem. Soc., Faraday Trans. 1, 1975, 71, 0, 35, https://doi.org/10.1039/f19757100035
. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Gas phase ion energetics data, Mass spectrum (electron ionization), References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid IE (evaluated) Recommended ionization energy Pc Critical pressure S°liquid Entropy of liquid at standard conditions Tboil Boiling point Tc Critical temperature Ttriple Triple point temperature ΔcH°liquid Enthalpy of combustion of liquid 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 - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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