Benzene, 1,2,3,4-tetrafluoro-
- Formula: C6H2F4
- Molecular weight: 150.0737
- IUPAC Standard InChIKey: SOZFIIXUNAKEJP-UHFFFAOYSA-N
- CAS Registry Number: 551-62-2
- 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: 1,2,3,4-Tetrafluorobenzene; 2,3,4,5-Tetrafluorobenzene
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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 by: Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
S°liquid | 61.21 | cal/mol*K | N/A | Andon and Martin, 1973 |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
45.39 | 298.15 | Andon and Martin, 1973 | T = 10 to 320 K. |
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
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 368.2 | K | N/A | Aldrich Chemical Company Inc., 1990 | BS |
Tboil | 368. | K | N/A | PCR Inc., 1990 | BS |
Tboil | 366.7 | K | N/A | Weast and Grasselli, 1989 | BS |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 231.25 | K | N/A | Andon and Martin, 1973, 2 | Crystal phase 2 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Ttriple | 233.26 | K | N/A | Andon and Martin, 1973, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 550.83 | K | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.2 K; TRC |
Tc | 550.83 | K | N/A | Hales and Townsend, 1974 | Uncertainty assigned by TRC = 0.05 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 37.41 | atm | N/A | Ambrose, Broderick, et al., 1974 | Uncertainty assigned by TRC = 0.04 atm; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 3.196 | mol/l | N/A | Hales and Townsend, 1974 | Uncertainty assigned by TRC = 0.0031 mol/l; Liquid density determined by magnetically balanced float up to 490 K, see J.L.Hales, 1970. Critical D by equation due to Riedel.; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 8.96 | kcal/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 300. to 390. K. See also Basarová and Svoboda, 1991.; AC |
Enthalpy of vaporization
ΔvapH (kcal/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
8.80 | 315. | A | Stephenson and Malanowski, 1987 | Based on data from 300. to 392. K. See also Ambrose, Ellender, et al., 1975 and Boublik, Fried, et al., 1984.; AC |
8.84 | 294. | MM | Stephenson and Malanowski, 1987 | Based on data from 279. to 323. K. See also Findlay, 1969.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (atm)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
279.20 to 323.02 | 4.31164 | 1394.889 | -44.425 | Findlay, 1969 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kcal/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
2.612 | 233.3 | Andon and Martin, 1973, 2 | AC |
Enthalpy of phase transition
ΔHtrs (kcal/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.171 | 221. | crystaline, II | crystaline, I | Andon and Martin, 1973 | DH |
1.477 | 231.25 | crystaline, II | liquid | Andon and Martin, 1973 | DH |
2.6123 | 233.26 | crystaline, I | liquid | Andon and Martin, 1973 | DH |
Entropy of phase transition
ΔStrs (cal/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
5.31 | 221. | crystaline, II | crystaline, I | Andon and Martin, 1973 | DH |
6.38 | 231.25 | crystaline, II | liquid | Andon and Martin, 1973 | DH |
11.2 | 233.26 | crystaline, I | liquid | Andon and Martin, 1973 | 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 as indicated in comments:
B - John E. Bartmess
RCD - Robert C. Dunbar
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
C6HF4- + =
By formula: C6HF4- + H+ = C6H2F4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 369.8 ± 2.1 | kcal/mol | G+TS | Buker, Nibbering, et al., 1997 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 361.6 ± 2.0 | kcal/mol | IMRE | Buker, Nibbering, et al., 1997 | gas phase; B |
By formula: Cr+ + C6H2F4 = (Cr+ • C6H2F4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 25.4 | kcal/mol | RAK | Ryzhov, 1999 | RCD |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 1.2350×10+6 | cal/mol*K | RAK | Ryzhov, 1999 | RCD |
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) | 9.57 ± 0.03 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 167.4 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 160.8 | kcal/mol | N/A | Hunter and Lias, 1998 | HL |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.60 | PE | Sell, Mintz, et al., 1978 | LLK |
9.532 ± 0.004 | EQ | Lias and Ausloos, 1978 | LLK |
9.61 | PI | Bralsford, Harris, et al., 1960 | RDSH |
9.56 | PE | Streets and Ceasar, 1973 | Vertical value; LLK |
De-protonation reactions
C6HF4- + =
By formula: C6HF4- + H+ = C6H2F4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 369.8 ± 2.1 | kcal/mol | G+TS | Buker, Nibbering, et al., 1997 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 361.6 ± 2.0 | kcal/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 by: 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: Cr+ + C6H2F4 = (Cr+ • C6H2F4)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 25.4 | kcal/mol | RAK | Ryzhov, 1999 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 1.2350×10+6 | cal/mol*K | RAK | Ryzhov, 1999 |
Mass spectrum (electron ionization)
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction 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
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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 | 118859 |
References
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction 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.
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]
Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc.,
Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [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]
Hales and Townsend, 1974
Hales, J.L.; Townsend, R.,
Liquid Densities from 293 to 490 K of Eight Fluorinated Aromatic Comp.,
J. Chem. Thermodyn., 1974, 6, 111-6. [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]
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]
Findlay, 1969
Findlay, T.J.V.,
Vapor pressures of fluorobenzenes from 5 to 50.deg.C,
J. Chem. Eng. Data, 1969, 14, 2, 229-231, https://doi.org/10.1021/je60041a012
. [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]
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]
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]
Sell, Mintz, et al., 1978
Sell, J.A.; Mintz, D.M.; Kupperman, A.,
Photoelectron angular distributions of carbon-carbon π electrons in ethylene, benzene, and their fluorinated derivatives,
Chem. Phys. Lett., 1978, 58, 601. [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]
Notes
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), References
- Symbols used in this document:
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 ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions ρc Critical density - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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