Benzene

• Formula: C₆H₆
• Molecular weight: 78.1118
• IUPAC Standard InChI: InChI=1S/C6H6/c1-2-4-6-5-3-1/h1-6H Copy

  
• IUPAC Standard InChIKey: UHOVQNZJYSORNB-UHFFFAOYSA-N Copy
• CAS Registry Number: 71-43-2
• 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.
• Isotopologues:
  • Benzene-D6
• Other names: [6]Annulene; Benzol; Benzole; Coal naphtha; Cyclohexatriene; Phenyl hydride; Pyrobenzol; Pyrobenzole; Benzolene; Bicarburet of hydrogen; Carbon oil; Mineral naphtha; Motor benzol; Benzeen; Benzen; Benzin; Benzine; Benzolo; Fenzen; NCI-C55276; Phene; Rcra waste number U019; UN 1114; NSC 67315; 1,3,5-Cyclohexatriene
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data (reactions 1 to 50)
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data: reactions 51 to 99
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • UV/Visible spectrum
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
  • Fluid Properties
• Data at other public NIST sites:
  • Electron-Impact Ionization Cross Sections (on physics web site)
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
  • NIST Polycyclic Aromatic Hydrocarbon Structure Index
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Gas phase thermochemistry data

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), 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:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Constant pressure heat capacity of gas

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Mass spectrum (electron ionization), 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.

Reactions 1 to 50

 +  = ( • )

By formula: Cl^- + C₆H₆ = (Cl^- • C₆H₆)

Free energy of reaction

C₆H₅^- +  =

By formula: C₆H₅^- + H⁺ = C₆H₆

C₆H₆⁺ +  = (C₆H₆⁺ • )

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

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

By formula: Li⁺ + C₆H₆ = (Li⁺ • C₆H₆)

 +  = ( • )

By formula: Br^- + C₆H₆ = (Br^- • C₆H₆)

Free energy of reaction

( • ) +  = ( • 2)

By formula: (Na⁺ • C₆H₆) + C₆H₆ = (Na⁺ • 2C₆H₆)

 +  = ( • )

By formula: Na⁺ + C₆H₆ = (Na⁺ • C₆H₆)

Free energy of reaction

C₉H₁₃N⁺ +  = (C₉H₁₃N⁺ • )

By formula: C₉H₁₃N⁺ + C₆H₆ = (C₉H₁₃N⁺ • C₆H₆)

Bond type: Charge transfer bond (positive ion)

Free energy of reaction

C₇H₉N⁺ +  = (C₇H₉N⁺ • )

By formula: C₇H₉N⁺ + C₆H₆ = (C₇H₉N⁺ • C₆H₆)

Bond type: Charge transfer bond (positive ion)

C₈H₁₁N⁺ +  = (C₈H₁₁N⁺ • )

By formula: C₈H₁₁N⁺ + C₆H₆ = (C₈H₁₁N⁺ • C₆H₆)

Bond type: Charge transfer bond (positive ion)

C₁₀H₁₀Fe⁺ +  = (C₁₀H₁₀Fe⁺ • )

By formula: C₁₀H₁₀Fe⁺ + C₆H₆ = (C₁₀H₁₀Fe⁺ • C₆H₆)

Free energy of reaction

( • ) +  = ( • 2)

By formula: (Co⁺ • C₆H₆) + C₆H₆ = (Co⁺ • 2C₆H₆)

Enthalpy of reaction

C₇H₈⁺ +  = (C₇H₈⁺ • )

By formula: C₇H₈⁺ + C₆H₆ = (C₇H₈⁺ • C₆H₆)

Bond type: Charge transfer bond (positive ion)

C₂H₇O⁺ +  = (C₂H₇O⁺ • )

By formula: C₂H₇O⁺ + C₆H₆ = (C₂H₇O⁺ • C₆H₆)

Free energy of reaction

( •  • ) +  = ( • 2 • )

By formula: (K⁺ • C₆H₆ • H₂O) + C₆H₆ = (K⁺ • 2C₆H₆ • H₂O)

( • 2 • ) +  = ( • 3 • )

By formula: (K⁺ • 2H₂O • C₆H₆) + H₂O = (K⁺ • 3H₂O • C₆H₆)

( •  • ) +  = ( • 2 • )

By formula: (K⁺ • H₂O • C₆H₆) + H₂O = (K⁺ • 2H₂O • C₆H₆)

 +  = ( • )

By formula: I^- + C₆H₆ = (I^- • C₆H₆)

C₃H₃⁺ +  = (C₃H₃⁺ • )

By formula: C₃H₃⁺ + C₆H₆ = (C₃H₃⁺ • C₆H₆)

( •  • 2) +  = ( • 2 • 2)

By formula: (K⁺ • H₂O • 2C₆H₆) + H₂O = (K⁺ • 2H₂O • 2C₆H₆)

(C₆H₆⁺ • 2) +  = (C₆H₆⁺ • 3)

By formula: (C₆H₆⁺ • 2C₆H₆) + C₆H₆ = (C₆H₆⁺ • 3C₆H₆)

Bond type: Charge transfer bond (positive ion)

( •  • 2) +  = ( • 2 • 2)

By formula: (K⁺ • C₆H₆ • 2H₂O) + C₆H₆ = (K⁺ • 2C₆H₆ • 2H₂O)

 +  = ( • )

By formula: Cr⁺ + C₆H₆ = (Cr⁺ • C₆H₆)

Enthalpy of reaction

( • 2) +  = ( •  • 2)

By formula: (K⁺ • 2C₆H₆) + H₂O = (K⁺ • H₂O • 2C₆H₆)

( • ) +  = ( •  • )

By formula: (K⁺ • C₆H₆) + H₂O = (K⁺ • H₂O • C₆H₆)

( • 2) +  = ( •  • 2)

By formula: (K⁺ • 2H₂O) + C₆H₆ = (K⁺ • C₆H₆ • 2H₂O)

( • 3) +  = ( •  • 3)

By formula: (K⁺ • 3H₂O) + C₆H₆ = (K⁺ • C₆H₆ • 3H₂O)

( • ) +  = ( •  • )

By formula: (K⁺ • H₂O) + C₆H₆ = (K⁺ • C₆H₆ • H₂O)

( • ) +  = ( • 2)

By formula: (Cr⁺ • C₆H₆) + C₆H₆ = (Cr⁺ • 2C₆H₆)

Enthalpy of reaction

 +  = ( • )

By formula: F^- + C₆H₆ = (F^- • C₆H₆)

 +  = ( • )

By formula: Mn⁺ + C₆H₆ = (Mn⁺ • C₆H₆)

Enthalpy of reaction

 +  = ( • )

By formula: V⁺ + C₆H₆ = (V⁺ • C₆H₆)

Enthalpy of reaction

 +  = ( • )

By formula: Fe⁺ + C₆H₆ = (Fe⁺ • C₆H₆)

Enthalpy of reaction

 +  = ( • )

By formula: Ti⁺ + C₆H₆ = (Ti⁺ • C₆H₆)

Enthalpy of reaction

( • ) +  = ( • 2)

By formula: (K⁺ • C₆H₆) + C₆H₆ = (K⁺ • 2C₆H₆)

C₄H₉⁺ +  = (C₄H₉⁺ • )

By formula: C₄H₉⁺ + C₆H₆ = (C₄H₉⁺ • C₆H₆)

(C₆H₆⁺ • ) +  = (C₆H₆⁺ • 2)

By formula: (C₆H₆⁺ • C₆H₆) + C₆H₆ = (C₆H₆⁺ • 2C₆H₆)

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

By formula: K⁺ + C₆H₆ = (K⁺ • C₆H₆)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₆H₆ = (C₆H₇N⁺ • C₆H₆)

Bond type: Charge transfer bond (positive ion)

C₁₁H₁₀⁺ +  = (C₁₁H₁₀⁺ • )

By formula: C₁₁H₁₀⁺ + C₆H₆ = (C₁₁H₁₀⁺ • C₆H₆)

Bond type: Charge transfer bond (positive ion)

C₆H₅Cl⁺ +  = (C₆H₅Cl⁺ • )

By formula: C₆H₅Cl⁺ + C₆H₆ = (C₆H₅Cl⁺ • C₆H₆)

Bond type: Charge transfer bond (positive ion)

C₉H₁₂⁺ +  = (C₉H₁₂⁺ • )

By formula: C₉H₁₂⁺ + C₆H₆ = (C₉H₁₂⁺ • C₆H₆)

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

By formula: NO^- + C₆H₆ = (NO^- • C₆H₆)

( • ) +  = ( • 2)

By formula: (Fe⁺ • C₆H₆) + C₆H₆ = (Fe⁺ • 2C₆H₆)

Enthalpy of reaction

( • ) +  = ( • 2)

By formula: (Ti⁺ • C₆H₆) + C₆H₆ = (Ti⁺ • 2C₆H₆)

Enthalpy of reaction

( • ) +  = ( • 2)

By formula: (Mn⁺ • C₆H₆) + C₆H₆ = (Mn⁺ • 2C₆H₆)

Enthalpy of reaction

( • ) +  = ( • 2)

By formula: (Ni⁺ • C₆H₆) + C₆H₆ = (Ni⁺ • 2C₆H₆)

Enthalpy of reaction

( • ) +  = ( • 2)

By formula: (Cu⁺ • C₆H₆) + C₆H₆ = (Cu⁺ • 2C₆H₆)

Enthalpy of reaction

(CAS Reg. No. 79431-04-2 • 4294967295) +  = CAS Reg. No. 79431-04-2

By formula: (CAS Reg. No. 79431-04-2 • 4294967295C₆H₆) + C₆H₆ = CAS Reg. No. 79431-04-2

 +  = ( • )

By formula: Ni⁺ + C₆H₆ = (Ni⁺ • C₆H₆)

Enthalpy of reaction

Mass spectrum (electron ionization)

Go To: Top, Gas phase thermochemistry data, 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 by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

References

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Roux, Temprado, et al., 2008
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Tschurl, M.; Ueberfluss, C.; Boesl, U., Anion photoelectron, photodetachment, and infrared dissociation spectra of Cl-center dot C6H6, Chem. Phys. Lett., 2007, 439, 1-3, 23-28, https://doi.org/10.1016/j.cplett.2007.03.059 . [all data]

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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]

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Chowdhury, S.; Kebarle, P., Role of Binding Energies in A^-.B and A.B^- Complexes in the Kinetics of Gas Phase Electron Transfer Reactions:A^- + B = A + B^- Involving Perfluoro Compounds: SF₆, C₆F₁₁CF₃, J. Chem. Phys., 1986, 85, 9, 4989, https://doi.org/10.1063/1.451687 . [all data]

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Davico, G.E.; Bierbaum, V.M.; Depuy, C.H.; Ellison, G.B.; Squires, R.R., The C-H bond energy of benzene, J. Am. Chem. Soc., 1995, 117, 9, 2590, https://doi.org/10.1021/ja00114a023 . [all data]

Ervin and DeTuro, 2002
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Meyer, Khan, et al., 1995
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Kemper, Bushnell, et al., 1993
Kemper, P.R.; Bushnell, J.; Von Koppen, P.; Bowers, M.T., Binding Energies of Co+(H2/CH4/C2H6)1,2,3 Clusters, J. Phys. Chem., 1993, 97, 9, 1810, https://doi.org/10.1021/j100111a016 . [all data]

Ernstberger, Krause, et al., 1990
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Deakyne and Meot-Ner (Mautner), 1985
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Searles and Kebarle, 1969
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Caldwell, Masucci, et al., 1989
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Lin and Dunbar, 1997
Lin, C.-Y.; Dunbar, R.C., Radiative Association Kinetics and Binding Energies of Chromium Ions with Benzene and Benzene Derivatives, Organometallics, 1997, 16, 12, 2691, https://doi.org/10.1021/om960949n . [all data]

Hiraoka, Mizuse, et al., 1987
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Gapeev and Dunbar, 2002
Gapeev, A.; Dunbar, R.C., Reactivity and Binding Energies of Transition Metal Halide Ions with Benzene, J. Am. Soc. Mass Spectrom., 2002, 13, 5, 477, https://doi.org/10.1016/S1044-0305(02)00373-2 . [all data]

Sen Sharma, Ikuta, et al., 1982
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El-Shall and Meot-Ner (Mautner), 1987
El-Shall, M.S.; Meot-Ner (Mautner), M., Ionic Charge Transfer Complexes. 3. Delocalised pi Systems as Electron Acceptors and Donors, J. Phys. Chem., 1987, 91, 5, 1088, https://doi.org/10.1021/j100289a017 . [all data]

Reents and Freiser, 1981
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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]

Lee and Squires, 1986
Lee, R.E.; Squires, R.R., Anionic homoaromaticity: A gas phase experimental study, J. Am. Chem. Soc., 1986, 105, 5078. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  T	Temperature
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

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