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
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data (reactions 1 to 50)
  • References
  • Notes
• Other data available:
  • Phase change data
  • Reaction thermochemistry data: reactions 51 to 99
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • 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
• Options:
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Gas phase thermochemistry data

Go To: Top, Condensed 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 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

Condensed phase thermochemistry data

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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
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

Constant pressure heat capacity of solid

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, 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.

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

References

Go To: Top, Gas phase thermochemistry data, 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.

Roux, Temprado, et al., 2008
Roux, M.V.; Temprado, M.; Chickos, J.S.; Nagano, Y., Critically Evaluated Thermochemical Properties of Polycyclic Aromatic Hydrocarbons, J. Phys. Chem. Ref. Data, 2008, 37, 4, 1855-1996. [all data]

Good and Smith, 1969
Good, W.D.; Smith, N.K., Enthalpies of combustion of toluene, benzene, cyclohexane, cyclohexene, methylcyclopentane, 1-methylcyclopentene, and n-hexane, J. Chem. Eng. Data, 1969, 14, 102-106. [all data]

Prosen, Gilmont, et al., 1945
Prosen, E.J.; Gilmont, R.; Rossini, F.D., Heats of combustion of benzene, toluene, ethyl-benzene, o-xylene, m-xylene, p-xylene, n-propylbenzene, and styrene, J. Res. NBS, 1945, 34, 65-70. [all data]

Prosen, Johnson, et al., 1946
Prosen, E.J.; Johnson, W.H.; Rossini, F.D., Heats of combustion and formation at 25°C of the alkylbenzenes through C₁₀H₁₄, and of the higher normal monoalkylbenzenes, J. Res. NBS, 1946, 36, 455-461. [all data]

Landrieu, Baylocq, et al., 1929
Landrieu, P.; Baylocq, F.; Johnson, J.R., Etude thermochimique dans la serie furanique, Bull. Soc. Chim. France, 1929, 45, 36-49. [all data]

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Montgomery J.B., The heat capacity of organic vapors. IV. Benzene, fluorobenzene, toluene, cyclohexane, methylcyclohexane and cyclohexene, J. Am. Chem. Soc., 1942, 64, 2375-2377. [all data]

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Oliver, G.D.; Eaton, M.; Huffman, H.M., The heat capacity, heat of fusion and entropy of benzene, J. Am. Chem. Soc., 1948, 70, 1502-1505. [all data]

Huffman, Parks, et al., 1930
Huffman, H.M.; Parks, G.S.; Daniels, A.C., Thermal data on organic compounds. VII. The heat capacities, entropies and free energies of twelve aromatic hydrocarbons, J. Am. Chem. Soc., 1930, 52, 1547-1558. [all data]

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Ahlberg, J.E.; Blanchard, E.R.; Lundberg, W.O., The heat capacities of benzene, methyl alcohol and glycerol at very low temperatures, J. Chem. Phys., 1937, 5, 537-551. [all data]

Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E., Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide, J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]

Czarnota, 1991
Czarnota, I., Heat capacity of benzene at high pressures, J. Chem. Thermodynam., 1991, 23, 25-30. [all data]

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Lainez, A.; Rodrigo, M.M.; Wilhelm, E.; Grolier, J.-P.E., Excess volumes and excess heaat capacitiies of some mixtures with trans,trans,cis-1,5,9-cyclododecatriene at 298.15K, J. Chem. Eng. Data, 1989, 34, 332-335. [all data]

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Shiohama, Y.; Ogawa, H.; Murakami, S.; Fujihara, I., Excess molar isobaric heat capacities and isentropic compressibilities of (cis- or trans-decalin + benzene or toluene or iso-octane or n-heptane) at 298.15 K, J. Chem. Thermodynam., 1988, 20, 1183-1189. [all data]

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Grolier, J.-P.E.; Roux-Desgranges, G.; Kooner, Z.S.; Smith, J.F.; Hepler, L.G., Thermal and volumetric properties of chloroform + benzene mixtures and the ideal associated solution model of complex formation, J. Solution Chem., 1987, 16, 745-752. [all data]

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Kalali, H.; Kohler, F.; Svejda, P., Excess properties of the mixture bis(2-dichlorethyl)ether (chlorex) + 2,2,4-trimethylpentane (isooctane), Monatsh. Chem., 1987, 118, 1-18. [all data]

Tanaka, 1987
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Tanaka, R., Excess heat capacities for mixtures of benzene with cyclopentane, methylcyclohexane, and cyclooctane at 298.15 K, J. Chem. Eng. Data, 1985, 30, 267-269. [all data]

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Grolier, J.-P.E.; Inglese, A.; Wilhelm, E., Excess volumes and excess heat capacities of tetrachloroethene + cyclohexane, + methylcyclohexane, + benzene, and + toluene at 298.15 K, J. Chem. Thermodynam., 1982, 14, 523-529. [all data]

Tanaka, 1982
Tanaka, R., Determination of excess heat capacities of (benzene + tetrachloromethane and + cyclohexane) between 293.15 and 303.15 K by use of a Picker flow calorimeter, J. Chem. Thermodynam., 1982, 14, 259-268. [all data]

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Findenegg, G.H.; Gruber, K.; Pereira, J.F.; Kohler, F., Kalorimetrische Messungen an Mischungen von Nichtelektrolyten, 1. Mitt.: Molwarme des Systems 1,2-Dibromathan-Benzol, Monatsh. Chem., 1965, 96, 669-678. [all data]

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Notes

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• Symbols used in this document:
  

  Cp,gas	Constant pressure heat capacity of gas
  Cp,liquid	Constant pressure heat capacity of liquid
  Cp,solid	Constant pressure heat capacity of solid
  S°liquid	Entropy of liquid at standard conditions
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  T	Temperature
  ΔcH°liquid	Enthalpy of combustion of liquid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid 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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