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
  • Gas phase ion energetics data
  • IR Spectrum
  • UV/Visible spectrum
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • Henry's Law data
  • Ion clustering data
  • Mass spectrum (electron ionization)
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
• 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) (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)

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

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

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, Gas phase ion energetics data, IR Spectrum, UV/Visible spectrum, Gas Chromatography, 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, 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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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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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]

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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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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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Paul and Kebarle, 1991
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Ryzhov, 1999
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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
  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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