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
  • Gas Chromatography
  • References
  • Notes
• Options:
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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) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    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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Additional Data

Gas Chromatography

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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

Kovats' RI, non-polar column, isothermal

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Kovats' RI, non-polar column, custom temperature program

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Kovats' RI, polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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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, Gas Chromatography, NIST Free Links, NIST Subscription Links, 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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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]

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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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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]

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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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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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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]

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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, 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.; 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
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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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