Benzene, fluoro-

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

  
• IUPAC Standard InChIKey: PYLWMHQQBFSUBP-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • References
  • Notes
• Other data available:
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• Options:
  • Switch to SI units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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

Constant pressure heat capacity of liquid

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

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kcal/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (atm)
    T = temperature (K)

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Enthalpy of fusion

Entropy of fusion

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^- +  =

By formula: C₆H₄F^- + H⁺ = C₆H₅F

 +  = ( • )

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

Free energy of reaction

C₆H₅F⁺ +  = (C₆H₅F⁺ • )

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

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₆H₆⁺ +  = (C₆H₆⁺ • )

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

Bond type: Charge transfer bond (positive ion)

C₆H₄F^- +  =

By formula: C₆H₄F^- + H⁺ = C₆H₅F

C₆H₄F^- +  =

By formula: C₆H₄F^- + H⁺ = C₆H₅F

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

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

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

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

 +  = ( • )

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

Free energy of reaction

C₇H₈⁺ +  = (C₇H₈⁺ • )

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

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

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

(V^- • ) +  = (V^- •  • )

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

V^- +  = (V^- • )

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

( • ) +  = ( • 2)

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

( • ) +  = ( • 2)

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

( • ) +  = ( • 2)

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

( • ) +  = ( • 2)

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

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

 +  = ( • )

By formula: K⁺ + C₆H₅F = (K⁺ • C₆H₅F)

 +  = ( • )

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

Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

k_H(T) = k°_H exp(d(ln(k_H))/d(1/T) ((1/T) - 1/(298.15 K)))
k°_H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(k_H))/d(1/T) = Temperature dependence constant (K)

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
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C₆H₅F⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₆H₄F^- +  =

By formula: C₆H₄F^- + H⁺ = C₆H₅F

C₆H₄F^- +  =

By formula: C₆H₄F^- + H⁺ = C₆H₅F

C₆H₄F^- +  =

By formula: C₆H₄F^- + H⁺ = C₆H₅F

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:
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. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

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

Free energy of reaction

C₆H₅F⁺ +  = (C₆H₅F⁺ • )

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

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₆H₆⁺ +  = (C₆H₆⁺ • )

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

Bond type: Charge transfer bond (positive ion)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

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

Bond type: Charge transfer bond (positive ion)

C₇H₈⁺ +  = (C₇H₈⁺ • )

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

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

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

Free energy of reaction

 +  = ( • )

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

 +  = ( • )

By formula: K⁺ + C₆H₅F = (K⁺ • C₆H₅F)

( • ) +  = ( • 2)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

 +  = ( • )

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

( • ) +  = ( • 2)

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

V^- +  = (V^- • )

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

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (50 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution
• SOLUTION (10% CCl4 FOR 3800-1300, 10% CS2 FOR 1300-450 CM^-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH I) FROM HARD COPY; 2 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

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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Additional Data

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, 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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For Zoom

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2.) Check here for automatic Y scaling

3.) Press here to zoom

Additional Data

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Ion clustering data, IR Spectrum, 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.

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]

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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]

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Goates, J.R.; Ott, J.B.; Moellmer, J.F., Solid + Liquid Phase Equilibria and Solid-compound Formation in Halobenzenes + Aromatic Hydrocarbons, J. Chem. Thermodyn., 1976, 8, 217. [all data]

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Timmermans, J., Researches in Stoichiometry. I. The Heat of Fusion of Organic Compounds., Bull. Soc. Chim. Belg., 1935, 44, 17-40. [all data]

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Scott, McCullough, et al., 1956, 2
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, 5457-63. [all data]

Stull, 1937, 2
Stull, D.R., A Semi-micro Calorimeter for Measuring Heat Capacities at Low Temp., J. Am. Chem. Soc., 1937, 59, 2726. [all data]

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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]

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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]

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Findlay, T.J.V., Vapor pressures of fluorobenzenes from 5° to 50°C, J. Chem. Eng. Data, 1969, 14, 229. [all data]

Scott, McCullough, et al., 1956, 3
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, 5457-54. [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]

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Young, S., On the Vapour-Pressures and Specific Volumes of Similar Compounds of Elements in Relation to the Position of those Elements in the Periodic Table, J. Chem. Soc., 1889, 55, 486-521, https://doi.org/10.1039/ct8895500486 . [all data]

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Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [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]

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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]

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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]

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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]

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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]

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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]

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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
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Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  Vc	Critical volume
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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