Benzene, fluoro-

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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
ΔrH°386.8 ± 2.1kcal/molG+TSBuker, Nibbering, et al., 1997gas phase; B
ΔrH°387.3 ± 2.1kcal/molG+TSAndrade and Riveros, 1996gas phase; B
ΔrH°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
ΔrH°387.2 ± 2.5kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
ΔrH°387.2 ± 5.4kcal/molG+TSBriscese and Riveros, 1975gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°378.6 ± 2.0kcal/molIMREBuker, Nibbering, et al., 1997gas phase; B
ΔrG°379.1 ± 2.0kcal/molIMREAndrade and Riveros, 1996gas phase; B
ΔrG°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
ΔrG°379.0 ± 2.6kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
ΔrG°379.0 ± 5.3kcal/molIMRBBriscese and Riveros, 1975gas phase; B

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

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

Quantity Value Units Method Reference Comment
ΔrH°10.6 ± 1.6kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
ΔrS°20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrG°2.1 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B

Free energy of reaction

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

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

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

Bond type: Charge transfer bond (positive ion)

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

Free energy of reaction

ΔrG° (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+ • Benzene, fluoro-)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
ΔrH°6.6kcal/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
ΔrH°17.0kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°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
ΔrH°399.60 ± 0.90kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
ΔrG°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
ΔrH°395.2 ± 2.0kcal/molBranWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B
Quantity Value Units Method Reference Comment
ΔrG°387.0 ± 2.1kcal/molH-TSWenthold and Squires, 1995gas phase; By HO- cleavage of substituted silanes; B

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

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

Bond type: Charge transfer bond (positive ion)

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

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

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

Quantity Value Units Method Reference Comment
ΔrH°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 • Benzene, fluoro-)

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

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

Free energy of reaction

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

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

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

Bond type: Charge transfer bond (positive ion)

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

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

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

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

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

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

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

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

By formula: V- + C6H5F = (V- • C6H5F)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

By formula: K+ + C6H5F = (K+ • C6H5F)

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

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

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

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

Mass spectrum (electron ionization)

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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

Spectrum

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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 Japan AIST/NIMC Database- Spectrum MS-NW- 529
NIST MS number 229256

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UV/Visible spectrum

Go To: Top, Reaction thermochemistry 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 by: Victor Talrose, Alexander N. Yermakov, Alexy A. Usov, Antonina A. Goncharova, Axlexander N. Leskin, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

Spectrum

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Additional Data

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Source Bowden and Braude, 1952
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. 11510
Instrument Hilger, Beckman spectrophotometer
Melting point - 42.2
Boiling point 84.7

References

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, Notes

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

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]

Bowden and Braude, 1952
Bowden, K.; Braude, E.A., J. Chem. Soc., 1952, 1068. [all data]

Notes

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