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Benzene, fluoro-

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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 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
DeltafH°liquid-36.04 ± 0.34kcal/molCcrGood, Scott, et al., 1956Corrected for CODATA value of «DELTA»fH; ALS
Quantity Value Units Method Reference Comment
DeltacH°liquid-741.86 ± 0.29kcal/molCcrGood, Scott, et al., 1956Corrected for CODATA value of «DELTA»fH; ALS
DeltacH°liquid-747.2kcal/molCcbSwarts, 1919Not corrected for CODATA value of «DELTA»fH; ALS
Quantity Value Units Method Reference Comment
S°liquid49.221cal/mol*KN/AScott, McCullough, et al., 1956DH
S°liquid46.61cal/mol*KN/AStull, 1937Extrapolation below 91 K, 42.55 J/mol*K.; DH

Constant pressure heat capacity of liquid

Cp,liquid (cal/mol*K) Temperature (K) Reference Comment
34.964298.15Roux, Grolier, et al., 1984DH
34.981298.15Scott, McCullough, et al., 1956T = 14 to 350 K.; DH
35.031298.1Stull, 1937T = 90 to 320 K.; 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
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. 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

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
DeltarH°386.8 ± 2.1kcal/molG+TSBuker, Nibbering, et al., 1997gas phase; B
DeltarH°387.3 ± 2.1kcal/molG+TSAndrade and Riveros, 1996gas phase; B
DeltarH°387.2 ± 2.5kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
DeltarH°387.2 ± 2.5kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
DeltarH°387.2 ± 5.4kcal/molG+TSBriscese and Riveros, 1975gas phase; B
Quantity Value Units Method Reference Comment
DeltarG°378.6 ± 2.0kcal/molIMREBuker, Nibbering, et al., 1997gas phase; B
DeltarG°379.1 ± 2.0kcal/molIMREAndrade and Riveros, 1996gas phase; B
DeltarG°378.9 ± 2.0kcal/molTDEqMeot-ner and Kafafi, 1988gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
DeltarG°379.0 ± 2.6kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
DeltarG°379.0 ± 5.3kcal/molIMRBBriscese and Riveros, 1975gas phase; B

Bromine anion + Benzene, fluoro- = (Bromine anion bullet Benzene, fluoro-)

By formula: Br- + C6H5F = (Br- bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°10.6 ± 1.6kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
DeltarS°20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
DeltarG°2.1 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
2.1423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

C6H5F+ + Benzene, fluoro- = (C6H5F+ bullet Benzene, fluoro-)

By formula: C6H5F+ + C6H5F = (C6H5F+ bullet C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
DeltarH°7.1kcal/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
DeltarH°14.1kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
DeltarS°27.cal/mol*KN/AMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
5.3356.PHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; Entropy change calculated or estimated; M

C6H6+ + Benzene, fluoro- = (C6H6+ bullet Benzene, fluoro-)

By formula: C6H6+ + C6H5F = (C6H6+ bullet C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
DeltarH°6.6kcal/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
DeltarH°17.0kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
DeltarS°30.cal/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
DeltarH°399.60 ± 0.90kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
DeltarG°391.8 ± 1.0kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

C6H4F- + Hydrogen cation = Benzene, fluoro-

By formula: C6H4F- + H+ = C6H5F

Quantity Value Units Method Reference Comment
DeltarH°395.2 ± 2.0kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
DeltarG°387.0 ± 2.1kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

C6H7N+ + Benzene, fluoro- = (C6H7N+ bullet Benzene, fluoro-)

By formula: C6H7N+ + C6H5F = (C6H7N+ bullet C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
DeltarH°11.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
DeltarS°26.5cal/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

Nitric oxide anion + Benzene, fluoro- = (Nitric oxide anion bullet Benzene, fluoro-)

By formula: NO- + C6H5F = (NO- bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°37.8kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Chlorine anion + Benzene, fluoro- = (Chlorine anion bullet Benzene, fluoro-)

By formula: Cl- + C6H5F = (Cl- bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarG°5.90kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (kcal/mol) T (K) Method Reference Comment
5.9300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

C7H8+ + Benzene, fluoro- = (C7H8+ bullet Benzene, fluoro-)

By formula: C7H8+ + C6H5F = (C7H8+ bullet C6H5F)

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
DeltarH°3.9kcal/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M

NH4+ + Benzene, fluoro- = (NH4+ bullet Benzene, fluoro-)

By formula: H4N+ + C6H5F = (H4N+ bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°14.4kcal/molPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M
Quantity Value Units Method Reference Comment
DeltarS°18.0cal/mol*KPHPMSDeakyne and Meot-Ner (Mautner), 1985gas phase; M

(V- bullet Benzene, fluoro-) + Benzene = (V- bullet Benzene bullet Benzene, fluoro-)

By formula: (V- bullet C6H5F) + C6H6 = (V- bullet C6H6 bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°3. ± 15.kcal/molN/AJudai, Hirano, et al., 1997gas phase; B

V- + Benzene, fluoro- = (V- bullet Benzene, fluoro-)

By formula: V- + C6H5F = (V- bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°14.4 ± 3.8kcal/molN/AJudai, Hirano, et al., 1997gas phase; B

(Lithium ion (1+) bullet Benzene, fluoro-) + Benzene, fluoro- = (Lithium ion (1+) bullet 2Benzene, fluoro-)

By formula: (Li+ bullet C6H5F) + C6H5F = (Li+ bullet 2C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°22.7 ± 0.7kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Sodium ion (1+) bullet Benzene, fluoro-) + Benzene, fluoro- = (Sodium ion (1+) bullet 2Benzene, fluoro-)

By formula: (Na+ bullet C6H5F) + C6H5F = (Na+ bullet 2C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°15.7 ± 0.9kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Cesium ion (1+) bullet Benzene, fluoro-) + Benzene, fluoro- = (Cesium ion (1+) bullet 2Benzene, fluoro-)

By formula: (Cs+ bullet C6H5F) + C6H5F = (Cs+ bullet 2C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°10.7 ± 1.1kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Rubidium ion (1+) bullet Benzene, fluoro-) + Benzene, fluoro- = (Rubidium ion (1+) bullet 2Benzene, fluoro-)

By formula: (Rb+ bullet C6H5F) + C6H5F = (Rb+ bullet 2C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°11.3 ± 1.2kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Potassium ion (1+) bullet Benzene, fluoro-) + Benzene, fluoro- = (Potassium ion (1+) bullet 2Benzene, fluoro-)

By formula: (K+ bullet C6H5F) + C6H5F = (K+ bullet 2C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°12.0 ± 0.7kcal/molCIDTAmunugama and Rodgers, 2002RCD

Lithium ion (1+) + Benzene, fluoro- = (Lithium ion (1+) bullet Benzene, fluoro-)

By formula: Li+ + C6H5F = (Li+ bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°35.1 ± 5.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

Sodium ion (1+) + Benzene, fluoro- = (Sodium ion (1+) bullet Benzene, fluoro-)

By formula: Na+ + C6H5F = (Na+ bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°16.7 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

Cesium ion (1+) + Benzene, fluoro- = (Cesium ion (1+) bullet Benzene, fluoro-)

By formula: Cs+ + C6H5F = (Cs+ bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°12.0 ± 1.2kcal/molCIDTAmunugama and Rodgers, 2002RCD

Rubidium ion (1+) + Benzene, fluoro- = (Rubidium ion (1+) bullet Benzene, fluoro-)

By formula: Rb+ + C6H5F = (Rb+ bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°12.8 ± 1.3kcal/molCIDTAmunugama and Rodgers, 2002RCD

Potassium ion (1+) + Benzene, fluoro- = (Potassium ion (1+) bullet Benzene, fluoro-)

By formula: K+ + C6H5F = (K+ bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°13.2 ± 0.7kcal/molCIDTAmunugama and Rodgers, 2002RCD

Chromium ion (1+) + Benzene, fluoro- = (Chromium ion (1+) bullet Benzene, fluoro-)

By formula: Cr+ + C6H5F = (Cr+ bullet C6H5F)

Quantity Value Units Method Reference Comment
DeltarH°39.2kcal/molRAKRyzhov, 1999RCD

References

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Good, Scott, et al., 1956
Good, W.D.; Scott, D.W.; Waddington, G., Combustion calorimetry of organic fluorine compounds by a rotating-bomb method, J. Phys. Chem., 1956, 60, 1080-1089. [all data]

Swarts, 1919
Swarts, F., Etudes thermochimiques sur les combinaisons organiques fluorees, J. Chim. Phys., 1919, 17, 3-70. [all data]

Scott, McCullough, et al., 1956
Scott, D.W.; McCullough, J.P.; Good, W.D.; Messerly, J.F.; Pennington, R.E.; Kincheloe, T.C.; Hossenlopp, I.A.; Douslin, D.R.; Waddington, G., Fluorobenzene: Thermodynamic properties in the solid, liquid and vapor states, a revised vibrational assignment, J. Am. Chem. Soc., 1956, 78, 5457-5463. [all data]

Stull, 1937
Stull, D.R., A semi-micro calorimeter for measuring heat capacities at low temperatures, J. Am. Chem. Soc., 1937, 59, 2726-2733. [all data]

Roux, Grolier, et al., 1984
Roux, A.H.; Grolier, J.-P.E.; Inglese, A.; Wilhelm, E., Excess molar enthalpies, excess molar heat capacities and excess molar volumes of (fluorobenzene + an n-alkane), Ber. Bunsenges. Phys. Chem., 1984, 88, 986-992. [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]

Andrade and Riveros, 1996
Andrade, P.B.M.; Riveros, J.M., Relative Gas-phase Acidities of Fluoro- and Chlorobenzene, J. Mass Spectrom., 1996, 31, 7, 767, https://doi.org/10.1002/(SICI)1096-9888(199607)31:7<767::AID-JMS345>3.0.CO;2-Q . [all data]

Meot-ner and Kafafi, 1988
Meot-ner, M.; Kafafi, S.A., Carbon Acidities of Aromatic Compounds, J. Am. Chem. Soc., 1988, 110, 19, 6297, https://doi.org/10.1021/ja00227a003 . [all data]

Kiefer, Zhang, et al., 1997
Kiefer, J.H.; Zhang, Q.; Kern, R.D.; Yao, J.; Jursic, B., Pyrolysis of Aromatic Azines: Pyrazine, Pyrimidine, and Pyridine, J. Phys. Chem. A, 1997, 101, 38, 7061, https://doi.org/10.1021/jp970211z . [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method, J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105 . [all data]

Briscese and Riveros, 1975
Briscese, S.M.J.; Riveros, J.M., Gas phase nucleophilic reactions of aromatic systems, J. Am. Chem. Soc., 1975, 97, 230. [all data]

Paul and Kebarle, 1991
Paul, G.J.C.; Kebarle, P., Stabilities of Complexes of Br- with Substituted Benzenes (SB) Based on Determinations of the Gas-Phase Equilibria Br- + SB = (BrSB)-, J. Am. Chem. Soc., 1991, 113, 4, 1148, https://doi.org/10.1021/ja00004a014 . [all data]

Ruhl, Bisling, et al., 1986
Ruhl, E.; Bisling, P.G.F.; Brutschy, B.; Baumgartel, H., Photoionization of Aromatic van der Waals Complexes in a Supersonic Jet, Chem. Phys. Lett., 1986, 126, 3-4, 232, https://doi.org/10.1016/S0009-2614(86)80075-6 . [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]

Meot-Ner (Mautner) and El-Shall, 1986
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

Farid and McMahon, 1978
Farid, R.; McMahon, T.B., Gas-Phase Ion-Molecule Reactions of Alkyl Nitrites by Ion Cyclotron Resonance Spectroscopy, Int. J. Mass Spectrom. Ion Phys., 1978, 27, 2, 163, https://doi.org/10.1016/0020-7381(78)80037-0 . [all data]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl- = RHCl-, Can. J. Chem., 1982, 60, 1907. [all data]

Deakyne and Meot-Ner (Mautner), 1985
Deakyne, C.A.; Meot-Ner (Mautner), M., Unconventional Ionic Hydrogen Bonds. 2. NH+ pi. Complexes of Onium Ions with Olefins and Benzene Derivatives, J. Am. Chem. Soc., 1985, 107, 2, 474, https://doi.org/10.1021/ja00288a034 . [all data]

Judai, Hirano, et al., 1997
Judai, K.; Hirano, M.; Kawamata, H.; Yabushita, S.; Nakajima, A.; Kaya, K., Formation of Vanadium-Arene Complex Anions and Their Photoelectron Spectroscopy, Chem. Phys. Lett., 1997, 270, 1-2, 23, https://doi.org/10.1016/S0009-2614(97)00336-9 . [all data]

Amunugama and Rodgers, 2002
Amunugama, R.; Rodgers, M.T., Influence of substituents on cation-pi interactions. 2. Absolute binding energies of alkali metal cation-fluorobenzene complexes determined by threshold collision-induced dissociation and theoretical studies, J. Phys. Chem. A, 2002, 106, 39, 9092, https://doi.org/10.1021/jp020459a . [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]

Notes

Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References