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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Condensed phase thermochemistry data
Go To: Top, Reaction thermochemistry 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 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 |
---|---|---|---|---|---|
![]() | -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 |
![]() | -741.86 ± 0.29 | kcal/mol | Ccr | Good, Scott, et al., 1956 | Corrected for CODATA value of «DELTA»fH; ALS |
![]() | -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
Cp,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 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- + =
By formula: C6H4F- + H+ = C6H5F
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 386.8 ± 2.1 | kcal/mol | G+TS | Buker, Nibbering, et al., 1997 | gas phase; B |
![]() | 387.3 ± 2.1 | kcal/mol | G+TS | Andrade and Riveros, 1996 | gas phase; B |
![]() | 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 |
![]() | 387.2 ± 2.5 | kcal/mol | Bran | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
![]() | 387.2 ± 5.4 | kcal/mol | G+TS | Briscese and Riveros, 1975 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 378.6 ± 2.0 | kcal/mol | IMRE | Buker, Nibbering, et al., 1997 | gas phase; B |
![]() | 379.1 ± 2.0 | kcal/mol | IMRE | Andrade and Riveros, 1996 | gas phase; B |
![]() | 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 |
![]() | 379.0 ± 2.6 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
![]() | 379.0 ± 5.3 | kcal/mol | IMRB | Briscese and Riveros, 1975 | gas phase; B |
By formula: Br- + C6H5F = (Br- C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 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 |
![]() | 20. | cal/mol*K | N/A | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 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
![]() |
T (K) | Method | Reference | Comment |
---|---|---|---|---|
2.1 | 423. | PHPMS | Paul and Kebarle, 1991 | gas phase; Entropy change calculated or estimated; M |
By formula: C6H5F+ + C6H5F = (C6H5F+ C6H5F)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 7.1 | kcal/mol | PI | Ruhl, Bisling, et al., 1986 | gas phase; from vIP of perpendicular dimer; M |
![]() | 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 |
![]() | 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
![]() |
T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.3 | 356. | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; Entropy change calculated or estimated; M |
By formula: C6H6+ + C6H5F = (C6H6+ C6H5F)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 6.6 | kcal/mol | PI | Ruhl, Bisling, et al., 1986 | gas phase; from vIP of perpendicular dimer; M |
![]() | 17.0 | kcal/mol | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 30. | cal/mol*K | PHPMS | Meot-Ner (Mautner), Hamlet, et al., 1978 | gas phase; M |
C6H4F- + =
By formula: C6H4F- + H+ = C6H5F
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 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 |
![]() | 391.8 ± 1.0 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
C6H4F- + =
By formula: C6H4F- + H+ = C6H5F
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 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 |
![]() | 387.0 ± 2.1 | kcal/mol | H-TS | Wenthold and Squires, 1995 | gas phase; By HO- cleavage of substituted silanes; B |
By formula: C6H7N+ + C6H5F = (C6H7N+ C6H5F)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 11.7 | kcal/mol | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 26.5 | cal/mol*K | PHPMS | Meot-Ner (Mautner) and El-Shall, 1986 | gas phase; M |
By formula: NO- + C6H5F = (NO- C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 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 |
By formula: Cl- + C6H5F = (Cl- C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 5.90 | kcal/mol | TDEq | French, Ikuta, et al., 1982 | gas phase; B |
Free energy of reaction
![]() |
T (K) | Method | Reference | Comment |
---|---|---|---|---|
5.9 | 300. | PHPMS | French, Ikuta, et al., 1982 | gas phase; M |
By formula: C7H8+ + C6H5F = (C7H8+ C6H5F)
Bond type: Charge transfer bond (positive ion)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 3.9 | kcal/mol | PI | Ruhl, Bisling, et al., 1986 | gas phase; from vIP of perpendicular dimer; M |
By formula: H4N+ + C6H5F = (H4N+ C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 14.4 | kcal/mol | PHPMS | Deakyne and Meot-Ner (Mautner), 1985 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
![]() | 18.0 | cal/mol*K | PHPMS | Deakyne and Meot-Ner (Mautner), 1985 | gas phase; M |
By formula: (V- C6H5F) + C6H6 = (V-
C6H6
C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 3. ± 15. | kcal/mol | N/A | Judai, Hirano, et al., 1997 | gas phase; B |
By formula: V- + C6H5F = (V- C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 14.4 ± 3.8 | kcal/mol | N/A | Judai, Hirano, et al., 1997 | gas phase; B |
By formula: (Li+ C6H5F) + C6H5F = (Li+
2C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 22.7 ± 0.7 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Na+ C6H5F) + C6H5F = (Na+
2C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 15.7 ± 0.9 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Cs+ C6H5F) + C6H5F = (Cs+
2C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 10.7 ± 1.1 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (Rb+ C6H5F) + C6H5F = (Rb+
2C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 11.3 ± 1.2 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: (K+ C6H5F) + C6H5F = (K+
2C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 12.0 ± 0.7 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Li+ + C6H5F = (Li+ C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 35.1 ± 5.0 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Na+ + C6H5F = (Na+ C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 16.7 ± 0.8 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Cs+ + C6H5F = (Cs+ C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 12.0 ± 1.2 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Rb+ + C6H5F = (Rb+ C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 12.8 ± 1.3 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: K+ + C6H5F = (K+ C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 13.2 ± 0.7 | kcal/mol | CIDT | Amunugama and Rodgers, 2002 | RCD |
By formula: Cr+ + C6H5F = (Cr+ C6H5F)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
![]() | 39.2 | kcal/mol | RAK | Ryzhov, 1999 | RCD |
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
- Symbols used in this document:
Cp,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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