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Benzene, 1,2,4,5-tetrafluoro-

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Gas 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-154.6 ± 0.81kcal/molCcrHarrop and Head, 1978 

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 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
Deltafliquid-163.42 ± 0.76kcal/molCcrHarrop and Head, 1978ALS
Quantity Value Units Method Reference Comment
Deltacliquid-640.30 ± 0.39kcal/molCcrHarrop and Head, 1978ALS
Quantity Value Units Method Reference Comment
liquid59.85cal/mol*KN/AAndon and Martin, 1973DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
45.94298.15Andon and Martin, 1973T = 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
Tboil363.KN/APCR Inc., 1990BS
Tboil362.7KN/AWeast and Grasselli, 1989BS
Quantity Value Units Method Reference Comment
Ttriple277.03KN/AAndon and Martin, 1973, 2Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Tc543.35KN/AAmbrose, Broderick, et al., 1974Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Pc37.51atmN/AAmbrose, Broderick, et al., 1974Uncertainty assigned by TRC = 0.06 atm; TRC
Quantity Value Units Method Reference Comment
Deltavap8.89kcal/molN/ABoublik, Fried, et al., 1984Based on data from 290. - 390. K. See also Basarová and Svoboda, 1991.; AC
Deltavap8.870kcal/molVFindlay, 1969ALS

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
7.91405.AStephenson and Malanowski, 1987Based on data from 390. - 488. K.; AC
7.79503.AStephenson and Malanowski, 1987Based on data from 488. - 543. K.; AC
8.80308.AStephenson and Malanowski, 1987Based on data from 293. - 390. K. See also Ambrose, Ellender, et al., 1975 and Boublik, Fried, et al., 1984.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
3.5970277.03Andon and Martin, 1973DH
3.597277.Andon and Martin, 1973, 2AC

Entropy of fusion

DeltafusS (cal/mol*K) Temperature (K) Reference Comment
12.99277.03Andon and Martin, 1973DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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:
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
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

C6H6+ + Benzene, 1,2,4,5-tetrafluoro- = (C6H6+ bullet Benzene, 1,2,4,5-tetrafluoro-)

By formula: C6H6+ + C6H2F4 = (C6H6+ bullet C6H2F4)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar12.0kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.cal/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

C6HF4- + Hydrogen cation = Benzene, 1,2,4,5-tetrafluoro-

By formula: C6HF4- + H+ = C6H2F4

Quantity Value Units Method Reference Comment
Deltar361.5 ± 2.1kcal/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Deltar353.3 ± 2.0kcal/molIMREBuker, Nibbering, et al., 1997gas phase; B

Chromium ion (1+) + Benzene, 1,2,4,5-tetrafluoro- = (Chromium ion (1+) bullet Benzene, 1,2,4,5-tetrafluoro-)

By formula: Cr+ + C6H2F4 = (Cr+ bullet C6H2F4)

Quantity Value Units Method Reference Comment
Deltar26.6kcal/molRAKRyzhov, 1999RCD

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 ± 0.07eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)178.4kcal/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity171.8kcal/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.2PEMaier and Thommen, 1981LLK
9.349 ± 0.004EQLias and Ausloos, 1978LLK
9.39PIBralsford, Harris, et al., 1960RDSH
9.36PEStreets and Ceasar, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H2F3+15.9 ± 0.1FEIMajer and Patrick, 1962RDSH

De-protonation reactions

C6HF4- + Hydrogen cation = Benzene, 1,2,4,5-tetrafluoro-

By formula: C6HF4- + H+ = C6H2F4

Quantity Value Units Method Reference Comment
Deltar361.5 ± 2.1kcal/molG+TSBuker, Nibbering, et al., 1997gas phase; B
Quantity Value Units Method Reference Comment
Deltar353.3 ± 2.0kcal/molIMREBuker, Nibbering, et al., 1997gas 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

C6H6+ + Benzene, 1,2,4,5-tetrafluoro- = (C6H6+ bullet Benzene, 1,2,4,5-tetrafluoro-)

By formula: C6H6+ + C6H2F4 = (C6H6+ bullet C6H2F4)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar12.0kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.cal/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

Chromium ion (1+) + Benzene, 1,2,4,5-tetrafluoro- = (Chromium ion (1+) bullet Benzene, 1,2,4,5-tetrafluoro-)

By formula: Cr+ + C6H2F4 = (Cr+ bullet C6H2F4)

Quantity Value Units Method Reference Comment
Deltar26.6kcal/molRAKRyzhov, 1999RCD

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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

Gas Phase Spectrum

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IR 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

This IR spectrum is from the NIST/EPA Gas-Phase Infrared Database .


Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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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Mass 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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


UV/Visible 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: Victor Talrose, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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UVVis spectrum
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Additional Data

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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

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

View large format table.

Column type Active phase Temperature (C) I Reference Comment
PackedSqualane100.604.Vernon and Edwards, 1975N2, DCMS-treated Celite; Column length: 1. m

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, 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]

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]

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]

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 «pi» 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]

Hitchcock, Fischer, et al., 1987
Hitchcock, H.P.; Fischer, P.; Gedanken, A.; Robin, M.B., Antibonding «alpha» valence MOs in the inner-shell and outer-shell spectra of the fluorobenzenes, J. Phys. Chem., 1987, 91, 531-540. [all data]

Vernon and Edwards, 1975
Vernon, F.; Edwards, G.T., Gas-liquid chromatography on fluorinated stationary phases. I. Hydrocarbons and fluorocarbons, J. Chromatogr., 1975, 110, 1, 73-80, https://doi.org/10.1016/S0021-9673(00)91212-3 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, Mass spectrum (electron ionization), UV/Visible spectrum, Gas Chromatography, NIST Free Links, References