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Benzene, fluoro-

Formula: C₆H₅F
Molecular weight: 96.1023
IUPAC Standard InChI:
InChI=1S/C6H5F/c7-6-4-2-1-3-5-6/h1-5H

Download the identifier in a file.
IUPAC Standard InChIKey: PYLWMHQQBFSUBP-UHFFFAOYSA-N
CAS Registry Number: 462-06-6
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: Fluorobenzene; Monofluorobenzene; Phenyl fluoride; UN 2387; Fluorobenzenes
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Other data available:
Data at other public NIST sites:
- Gas Phase Kinetics Database
- X-ray Photoelectron Spectroscopy Database, version 4.1
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Condensed phase thermochemistry data

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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
_fH°_liquid	-36.04 ± 0.34	kcal/mol	Ccr	Good, Scott, et al., 1956	Corrected for CODATA value of «DELTA»_fH; ALS
Quantity	Value	Units	Method	Reference	Comment
_cH°_liquid	-741.86 ± 0.29	kcal/mol	Ccr	Good, Scott, et al., 1956	Corrected for CODATA value of «DELTA»_fH; ALS
_cH°_liquid	-747.2	kcal/mol	Ccb	Swarts, 1919	Not corrected for CODATA value of «DELTA»_fH; ALS
Quantity	Value	Units	Method	Reference	Comment
S°_liquid	49.221	cal/mol*K	N/A	Scott, McCullough, et al., 1956	DH
S°_liquid	46.61	cal/mol*K	N/A	Stull, 1937	Extrapolation below 91 K, 42.55 J/mol*K.; DH

Constant pressure heat capacity of liquid

C_p,liquid (cal/mol*K)	Temperature (K)	Reference	Comment
34.964	298.15	Roux, Grolier, et al., 1984	DH
34.981	298.15	Scott, McCullough, et al., 1956	T = 14 to 350 K.; DH
35.031	298.1	Stull, 1937	T = 90 to 320 K.; DH

Reaction thermochemistry data

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

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^- + = Benzene, fluoro-

By formula: C₆H₄F^- + H⁺ = C₆H₅F

Quantity	Value	Units	Method	Reference	Comment
_rH°	386.8 ± 2.1	kcal/mol	G+TS	Buker, Nibbering, et al., 1997	gas phase; B
_rH°	387.3 ± 2.1	kcal/mol	G+TS	Andrade and Riveros, 1996	gas phase; B
_rH°	387.2 ± 2.5	kcal/mol	TDEq	Meot-ner and Kafafi, 1988	gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
_rH°	387.2 ± 2.5	kcal/mol	Bran	Wenthold and Squires, 1995	gas phase; By HO- cleavage of substituted silanes; B
_rH°	387.2 ± 5.4	kcal/mol	G+TS	Briscese and Riveros, 1975	gas phase; B
Quantity	Value	Units	Method	Reference	Comment
_rG°	378.6 ± 2.0	kcal/mol	IMRE	Buker, Nibbering, et al., 1997	gas phase; B
_rG°	379.1 ± 2.0	kcal/mol	IMRE	Andrade and Riveros, 1996	gas phase; B
_rG°	378.9 ± 2.0	kcal/mol	TDEq	Meot-ner and Kafafi, 1988	gas phase; anchored to 88MEO scale, not the "87 acidity scale". The Kiefer, Zhang, et al., 1997 BDE is for ortho.; B
_rG°	379.0 ± 2.6	kcal/mol	H-TS	Wenthold and Squires, 1995	gas phase; By HO- cleavage of substituted silanes; B
_rG°	379.0 ± 5.3	kcal/mol	IMRB	Briscese and Riveros, 1975	gas phase; B

+ Benzene, fluoro- = ( )

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

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

Free energy of reaction

_rG° (kcal/mol)	T (K)	Method	Reference	Comment
2.1	423.	PHPMS	Paul and Kebarle, 1991	gas phase; Entropy change calculated or estimated; M

C₆H₅F⁺ + Benzene, fluoro- = (C₆H₅F⁺ )

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

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
_rH°	7.1	kcal/mol	PI	Ruhl, Bisling, et al., 1986	gas phase; from vIP of perpendicular dimer; M
_rH°	14.1	kcal/mol	PHPMS	Meot-Ner (Mautner), Hamlet, et al., 1978	gas phase; Entropy change calculated or estimated; M
Quantity	Value	Units	Method	Reference	Comment
_rS°	27.	cal/mol*K	N/A	Meot-Ner (Mautner), Hamlet, et al., 1978	gas phase; Entropy change calculated or estimated; M

Free energy of reaction

_rG° (kcal/mol)	T (K)	Method	Reference	Comment
5.3	356.	PHPMS	Meot-Ner (Mautner), Hamlet, et al., 1978	gas phase; Entropy change calculated or estimated; M

C₆H₆⁺ + Benzene, fluoro- = (C₆H₆⁺ )

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

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
_rH°	6.6	kcal/mol	PI	Ruhl, Bisling, et al., 1986	gas phase; from vIP of perpendicular dimer; M
_rH°	17.0	kcal/mol	PHPMS	Meot-Ner (Mautner), Hamlet, et al., 1978	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
_rS°	30.	cal/mol*K	PHPMS	Meot-Ner (Mautner), Hamlet, et al., 1978	gas phase; M

C₆H₄F^- + = Benzene, fluoro-

By formula: C₆H₄F^- + H⁺ = C₆H₅F

Quantity	Value	Units	Method	Reference	Comment
_rH°	399.60 ± 0.90	kcal/mol	Bran	Wenthold and Squires, 1995	gas phase; By HO- cleavage of substituted silanes; B
Quantity	Value	Units	Method	Reference	Comment
_rG°	391.8 ± 1.0	kcal/mol	H-TS	Wenthold and Squires, 1995	gas phase; By HO- cleavage of substituted silanes; B

C₆H₄F^- + = Benzene, fluoro-

By formula: C₆H₄F^- + H⁺ = C₆H₅F

Quantity	Value	Units	Method	Reference	Comment
_rH°	395.2 ± 2.0	kcal/mol	Bran	Wenthold and Squires, 1995	gas phase; By HO- cleavage of substituted silanes; B
Quantity	Value	Units	Method	Reference	Comment
_rG°	387.0 ± 2.1	kcal/mol	H-TS	Wenthold and Squires, 1995	gas phase; By HO- cleavage of substituted silanes; B

C₆H₇N⁺ + Benzene, fluoro- = (C₆H₇N⁺ )

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

Bond type: Charge transfer bond (positive ion)

Quantity	Value	Units	Method	Reference	Comment
_rH°	11.7	kcal/mol	PHPMS	Meot-Ner (Mautner) and El-Shall, 1986	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
_rS°	26.5	cal/mol*K	PHPMS	Meot-Ner (Mautner) and El-Shall, 1986	gas phase; M

+ Benzene, fluoro- = ( )

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

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

+ Benzene, fluoro- = ( )

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

Quantity	Value	Units	Method	Reference	Comment
_rG°	5.90	kcal/mol	TDEq	French, Ikuta, et al., 1982	gas phase; B

Free energy of reaction

_rG° (kcal/mol)	T (K)	Method	Reference	Comment
5.9	300.	PHPMS	French, Ikuta, et al., 1982	gas phase; M

C₇H₈⁺ + Benzene, fluoro- = (C₇H₈⁺ )

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

Bond type: Charge transfer bond (positive ion)

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

+ Benzene, fluoro- = ( )

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

Quantity	Value	Units	Method	Reference	Comment
_rH°	14.4	kcal/mol	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M
Quantity	Value	Units	Method	Reference	Comment
_rS°	18.0	cal/mol*K	PHPMS	Deakyne and Meot-Ner (Mautner), 1985	gas phase; M

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

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

Quantity	Value	Units	Method	Reference	Comment
_rH°	3. ± 15.	kcal/mol	N/A	Judai, Hirano, et al., 1997	gas phase; B

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

By formula: V^- + C₆H₅F = (V^- C₆H₅F)

Quantity	Value	Units	Method	Reference	Comment
_rH°	14.4 ± 3.8	kcal/mol	N/A	Judai, Hirano, et al., 1997	gas phase; B

( Benzene, fluoro- ) + = ( 2)

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

Quantity	Value	Units	Method	Reference	Comment
_rH°	22.7 ± 0.7	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

( Benzene, fluoro- ) + = ( 2)

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

Quantity	Value	Units	Method	Reference	Comment
_rH°	15.7 ± 0.9	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

( Benzene, fluoro- ) + = ( 2)

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

Quantity	Value	Units	Method	Reference	Comment
_rH°	10.7 ± 1.1	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

( Benzene, fluoro- ) + = ( 2)

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

Quantity	Value	Units	Method	Reference	Comment
_rH°	11.3 ± 1.2	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

( Benzene, fluoro- ) + = ( 2)

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

Quantity	Value	Units	Method	Reference	Comment
_rH°	12.0 ± 0.7	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

+ Benzene, fluoro- = ( )

By formula: Li⁺ + C₆H₅F = (Li⁺ C₆H₅F)

Quantity	Value	Units	Method	Reference	Comment
_rH°	35.1 ± 5.0	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

+ Benzene, fluoro- = ( )

By formula: Na⁺ + C₆H₅F = (Na⁺ C₆H₅F)

Quantity	Value	Units	Method	Reference	Comment
_rH°	16.7 ± 0.8	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

+ Benzene, fluoro- = ( )

By formula: Cs⁺ + C₆H₅F = (Cs⁺ C₆H₅F)

Quantity	Value	Units	Method	Reference	Comment
_rH°	12.0 ± 1.2	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

+ Benzene, fluoro- = ( )

By formula: Rb⁺ + C₆H₅F = (Rb⁺ C₆H₅F)

Quantity	Value	Units	Method	Reference	Comment
_rH°	12.8 ± 1.3	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

+ Benzene, fluoro- = ( )

By formula: K⁺ + C₆H₅F = (K⁺ C₆H₅F)

Quantity	Value	Units	Method	Reference	Comment
_rH°	13.2 ± 0.7	kcal/mol	CIDT	Amunugama and Rodgers, 2002	RCD

+ Benzene, fluoro- = ( )

By formula: Cr⁺ + C₆H₅F = (Cr⁺ C₆H₅F)

Quantity	Value	Units	Method	Reference	Comment
_rH°	39.2	kcal/mol	RAK	Ryzhov, 1999	RCD

References

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

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

Symbols used in this document:

C_p,liquid	Constant pressure heat capacity of liquid
S°_liquid	Entropy of liquid at standard conditions
T	Temperature
_cH°_liquid	Enthalpy of combustion of liquid at standard conditions
_fH°_liquid	Enthalpy of formation of liquid at standard conditions
_rG°	Free energy of reaction at standard conditions
_rH°	Enthalpy of reaction at standard conditions
_rS°	Entropy of reaction at standard conditions

Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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