Toluene

• Formula: C₇H₈
• Molecular weight: 92.1384
• IUPAC Standard InChI: InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3 Copy

  
• IUPAC Standard InChIKey: YXFVVABEGXRONW-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-88-3
• 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:
  • Toluene-D3
  • Toluene-D8
• Other names: Benzene, methyl; Methacide; Methylbenzene; Methylbenzol; Phenylmethane; Antisal 1a; Toluol; Methane, phenyl-; NCI-C07272; Tolueen; Toluen; Toluolo; Rcra waste number U220; Tolu-sol; UN 1294; Dracyl; Monomethyl benzene; CP 25; NSC 406333; methylbenzene (toluene)
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • UV/Visible spectrum
  • Gas Chromatography
  • Fluid Properties
• Data at other public NIST sites:
  • Microwave spectra (on physics lab 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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Reaction thermochemistry data

Go To: Top, Gas phase ion energetics 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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

C₇H₇^- +  =

By formula: C₇H₇^- + H⁺ = C₇H₈

C₃H₉Si⁺ +  = (C₃H₉Si⁺ • )

By formula: C₃H₉Si⁺ + C₇H₈ = (C₃H₉Si⁺ • C₇H₈)

Free energy of reaction

 +  = ( • )

By formula: Br^- + C₇H₈ = (Br^- • C₇H₈)

Free energy of reaction

C₄H₉⁺ +  = (C₄H₉⁺ • )

By formula: C₄H₉⁺ + C₇H₈ = (C₄H₉⁺ • C₇H₈)

C₇H₈⁺ +  = (C₇H₈⁺ • )

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

Bond type: Charge transfer bond (positive ion)

C₆H₇N⁺ +  = (C₆H₇N⁺ • )

By formula: C₆H₇N⁺ + C₇H₈ = (C₆H₇N⁺ • C₇H₈)

Bond type: Charge transfer bond (positive ion)

C₉H₁₂⁺ +  = (C₉H₁₂⁺ • )

By formula: C₉H₁₂⁺ + C₇H₈ = (C₉H₁₂⁺ • C₇H₈)

Bond type: Charge transfer bond (positive ion)

 +  = ( • )

By formula: NO^- + C₇H₈ = (NO^- • C₇H₈)

 +  =  + 

By formula: HBr + C₇H₇Br = C₇H₈ + Br₂

 +  = ( • )

By formula: Cl^- + C₇H₈ = (Cl^- • C₇H₈)

Free energy of reaction

 +  =  + 

By formula: HI + C₇H₇I = C₇H₈ + I₂

 + 0.5 =  + 0.5

By formula: C₇H₇Br + 0.5H₂ = C₇H₈ + 0.5Br₂

 +  = ( • )

By formula: I^- + C₇H₈ = (I^- • C₇H₈)

=

By formula: C₇H₈ = C₇H₈

=  + 0.5

By formula: C₇H₇I = C₇H₈ + 0.5I₂

( • ) +  = ( • 2)

By formula: (Li⁺ • C₇H₈) + C₇H₈ = (Li⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (Na⁺ • C₇H₈) + C₇H₈ = (Na⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (Cs⁺ • C₇H₈) + C₇H₈ = (Cs⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (Rb⁺ • C₇H₈) + C₇H₈ = (Rb⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (K⁺ • C₇H₈) + C₇H₈ = (K⁺ • 2C₇H₈)

( • ) +  = ( • 2)

By formula: (Cr⁺ • C₇H₈) + C₇H₈ = (Cr⁺ • 2C₇H₈)

 +  =  + 

By formula: C₁₀H₁₄ + C₆H₆ = C₇H₈ + C₉H₁₂

 +  = ( • )

By formula: Li⁺ + C₇H₈ = (Li⁺ • C₇H₈)

 +  = ( • )

By formula: Na⁺ + C₇H₈ = (Na⁺ • C₇H₈)

 +  = ( • )

By formula: Cs⁺ + C₇H₈ = (Cs⁺ • C₇H₈)

 +  = ( • )

By formula: Rb⁺ + C₇H₈ = (Rb⁺ • C₇H₈)

 +  = ( • )

By formula: K⁺ + C₇H₈ = (K⁺ • C₇H₈)

 +  = ( • )

By formula: Cr⁺ + C₇H₈ = (Cr⁺ • C₇H₈)

Gas phase ion energetics data

Go To: Top, 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 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
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
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

View reactions leading to C₇H₈⁺ (ion structure unspecified)

Proton affinity at 298K

Gas basicity at 298K

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₇H₇^- +  =

By formula: C₇H₇^- + H⁺ = C₇H₈

References

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Notes

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

Gunion, Gilles, et al., 1992
Gunion, R.F.; Gilles, M.K.; Polak, M.L.; Lineberger, W.C., Ultraviolet Photoelectron Spectroscopy of the Phenide, Benzyl, and Phenoxide Anions., Int. J. Mass Spectrom. Ion Proc., 1992, 117, 601, https://doi.org/10.1016/0168-1176(92)80115-H . [all data]

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Stone, J.M.; Stone, J.A., A High Pressure Mass Spectrometric Study of the Binding of (CH3)3Si+ and (CH3)3C+ to Toluene and Benzene, Int. J. Mass Spectrom. Ion Proc., 1991, 109, 247, https://doi.org/10.1016/0168-1176(91)85107-W . [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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Benson, S.W.; Buss, J.H., The thermodynamics of bromination of toluene and the heat of formation of the benzyl radical, J. Phys. Chem., 1957, 61, 104-109. [all data]

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Ashcroft, S.J.; Carson, A.S.; Pedley, J.B., Thermochemistry of reductions caused by lithium aluminium hydride. Part 2.-The heats of formation of benzyl bromide, benzyl iodide and the benzyl radical, Trans. Faraday Soc., 1963, 59, 2713-2717. [all data]

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Caldwell, G.W.; Masucci, J.A.; Ikonomou, M.G., Negative Ion Chemical Ionization Mass Spectrometry - Binding of Molecules to Bromide and Iodide Anions, Org. Mass Spectrom., 1989, 24, 1, 8, https://doi.org/10.1002/oms.1210240103 . [all data]

Bartmess and Griffith, 1990
Bartmess, J.E.; Griffith, S.S., Tautomerization energetics of benzoannelated toluenes, J. Am. Chem. Soc., 1990, 112, 2931-2936. [all data]

Amunugama and Rodgers, 2002
Amunugama, R.; Rodgers, M.T., Influence of substituents on cation-pi interactions. 1. Absolute binding energies of alkali metal cation-toluene complexes determined by threshold collision-induced dissociation and theoretical studies, J. Phys. Chem. A, 2002, 106, 22, 5529, https://doi.org/10.1021/jp014307b . [all data]

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]

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Tsvetkov, V.F.; Rozhnov, A.M.; Nesterova, T.N., Study of the equilibrium of isomerization and transalkylation of isopropyltoluenes, Neftekhimiya, 1985, 53-57. [all data]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

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Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

Lu, Eiden, et al., 1992
Lu, K.-T.; Eiden, G.C.; Weisshaar, J.C., Toluene cation: nearly free rotation of the methyl group, J. Phys. Chem., 1992, 96, 9742. [all data]

Klasinc, Kovac, et al., 1983
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Selim and Helal, 1982
Selim, E.T.M.; Helal, A.I., The study of C₁-C₃ monosubstituted alkyl benzenes by the inverse convolution of first differential ionization efficiency curves, Org. Mass Spectrom., 1982, 17, 539. [all data]

Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S., Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]

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McLoughlin, R.G.; Morrison, J.D.; Traeger, J.C., Photoionization of the C-1 - C-4 monosubstituted alkyl benzenes: Thermochemistry of [C₇H₇]⁺ and [C₈H₉]⁺ formation, Org. Mass Spectrom., 1979, 14, 104. [all data]

Traeger and McLoughlin, 1978
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Lias and Ausloos, 1978
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Huang, F.-S.; Dunbar, R.C., Time-resolved photodissociation of toluene ion [E_o(C₆H₅CH₃⁺ Ü C₇H₇⁺ + H)=2.11 eV; cited data derived using evaluated IP for toluene. Modeling uncertainties give considerable latitude in the assignment of kinetic parameters.], Int. J. Mass Spectrom. Ion Processes, 1991, 109, 151. [all data]

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Nounou, P., Etude des composes aromatiques par spectrometrie de masse. I. Mesure des potentials d'ionisation et d'apparition par la methode du potential retardateur et interpretation des courbes d'ionisation differentielle, J. Chim. Phys., 1966, 63, 994. [all data]

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Lifshitz, C.; Gotkis, Y.; Ioffe, A.; Laskin, J.; Shaik, S., Is the tropylium ion (Tr⁺) formed from toluene at its thermochemical threshold?, Int. J. Mass Spectrom. Ion Processes, 1993, 125, R7. [all data]

Lifshitz, Gotkis, et al., 1993, 2
Lifshitz, C.; Gotkis, Y.; Laskin, J.; Ioffe, A.; Shaik, S., Threshold formation of benzylium (Bz⁺) and tropylium (Tr⁺) from toluene. Nonstatistical behavior in Franck-Condon gaps, J. Phys. Chem., 1993, 97, 12291. [all data]

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Bombach, Dannacher, et al., 1983, 2
Bombach, R.; Dannacher, J.; Stadelmann, J.-P., The rate-energy functions for the formation of tropylium and benzylium ions from toluene molecular cations, Chem. Phys. Lett., 1983, 95, 259. [all data]

Notes

Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  T	Temperature
  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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