Toluene

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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
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- + Hydrogen cation = Toluene

By formula: C7H7- + H+ = C7H8

Quantity Value Units Method Reference Comment
ΔrH°382.33 ± 0.45kcal/molD-EAGunion, Gilles, et al., 1992gas phase; Kim, Wenthold, et al., 1999, with LN2 cooling of the ion, gives the same EA; B
ΔrH°380.8 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
ΔrH°379.2 ± 2.1kcal/molG+TSGal, Decouzon, et al., 2001gas phase; B
ΔrH°377.0 ± 3.5kcal/molCIDTGraul and Squires, 1990gas phase; B
ΔrH°384.5 ± 7.1kcal/molG+TSBohme and Young, 1971gas phase; B
Quantity Value Units Method Reference Comment
ΔrG°373.7 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
ΔrG°372.1 ± 2.0kcal/molIMREGal, Decouzon, et al., 2001gas phase; B
ΔrG°377.4 ± 7.0kcal/molIMRBBohme and Young, 1971gas phase; B

C3H9Si+ + Toluene = (C3H9Si+ • Toluene)

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

Quantity Value Units Method Reference Comment
ΔrH°28.4kcal/molPHPMSStone and Stone, 1991gas phase; forms pi complex; M
ΔrH°31.3kcal/molPHPMSStone and Stone, 1991gas phase; toluene D8, forms pi complex; M
ΔrH°26.6kcal/molPHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H6, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrS°34.9cal/mol*KN/AWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H6, Entropy change calculated or estimated; M

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
10.3468.PHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H6, Entropy change calculated or estimated; M

Bromine anion + Toluene = (Bromine anion • Toluene)

By formula: Br- + C7H8 = (Br- • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°8.6 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
ΔrS°20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
ΔrG°0.1 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; ΔGaff measured at 303 K, corrected to 423 K, ΔSaff taken as that of PhNO2..Br-; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
0.1423.PHPMSPaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M

C4H9+ + Toluene = (C4H9+ • Toluene)

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

Quantity Value Units Method Reference Comment
ΔrH°28.6kcal/molPHPMSStone and Stone, 1991gas phase; toluene D8, forms protonated t-butyltoluene; M
ΔrH°29.1kcal/molPHPMSStone and Stone, 1991gas phase; forms protomated t-butyltoluene; M
Quantity Value Units Method Reference Comment
ΔrS°54.5cal/mol*KPHPMSStone and Stone, 1991gas phase; toluene D8, forms protonated t-butyltoluene; M
ΔrS°54.6cal/mol*KPHPMSStone and Stone, 1991gas phase; forms protomated t-butyltoluene; M

C7H8+ + Toluene = (C7H8+ • Toluene)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
ΔrH°14.5kcal/molMPIErnstberger, Krause, et al., 1990gas phase; M
ΔrH°5.4kcal/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
ΔrH°16.0kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°29.cal/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

C6H7N+ + Toluene = (C6H7N+ • Toluene)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
ΔrH°13.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°26.0cal/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

C9H12+ + Toluene = (C9H12+ • Toluene)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
ΔrH°12.0kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
ΔrS°27.cal/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

Nitric oxide anion + Toluene = (Nitric oxide anion • Toluene)

By formula: NO- + C7H8 = (NO- • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°44.2kcal/molICRReents and Freiser, 1981gas phase; switching reaction,Thermochemical ladder(NO+)C2H5OH, Entropy change calculated or estimated; Farid and McMahon, 1978; M

Hydrogen bromide + Benzene, (bromomethyl)- = Toluene + Bromine

By formula: HBr + C7H7Br = C7H8 + Br2

Quantity Value Units Method Reference Comment
ΔrH°8.1 ± 1.0kcal/molEqkBenson and Buss, 1957gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 8.0 ± 0.9 kcal/mol; ALS

Chlorine anion + Toluene = (Chlorine anion • Toluene)

By formula: Cl- + C7H8 = (Cl- • C7H8)

Quantity Value Units Method Reference Comment
ΔrG°4.00kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

ΔrG° (kcal/mol) T (K) Method Reference Comment
4.0300.PHPMSFrench, Ikuta, et al., 1982gas phase; M

Hydrogen iodide + Benzene, (iodomethyl)- = Toluene + Iodine

By formula: HI + C7H7I = C7H8 + I2

Quantity Value Units Method Reference Comment
ΔrH°-7.8 ± 1.1kcal/molCmGraham, Nichol, et al., 1955liquid phase; solvent: p-Xylene; ALS

Benzene, (bromomethyl)- + 0.5Hydrogen = Toluene + 0.5Bromine

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

Quantity Value Units Method Reference Comment
ΔrH°-0.9 ± 0.5kcal/molChydAshcroft, Carson, et al., 1963liquid phase; ALS

Iodide + Toluene = (Iodide • Toluene)

By formula: I- + C7H8 = (I- • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°11.0 ± 1.0kcal/molTDAsCaldwell, Masucci, et al., 1989gas phase; B,M

5-Methylene 1,3-cyclohexadiene = Toluene

By formula: C7H8 = C7H8

Quantity Value Units Method Reference Comment
ΔrH°-24. ± 3.kcal/molCmBartmess and Griffith, 1990gas phase; Gas phase acidity; ALS

Benzene, (iodomethyl)- = Toluene + 0.5Iodine

By formula: C7H7I = C7H8 + 0.5I2

Quantity Value Units Method Reference Comment
ΔrH°-9.7 ± 0.4kcal/molChydAshcroft, Carson, et al., 1963liquid phase; ALS

(Lithium ion (1+) • Toluene) + Toluene = (Lithium ion (1+) • 2Toluene)

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

Quantity Value Units Method Reference Comment
ΔrH°27.8 ± 0.7kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Sodium ion (1+) • Toluene) + Toluene = (Sodium ion (1+) • 2Toluene)

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

Quantity Value Units Method Reference Comment
ΔrH°20.7 ± 0.5kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Cesium ion (1+) • Toluene) + Toluene = (Cesium ion (1+) • 2Toluene)

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

Quantity Value Units Method Reference Comment
ΔrH°14.7 ± 1.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Rubidium ion (1+) • Toluene) + Toluene = (Rubidium ion (1+) • 2Toluene)

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

Quantity Value Units Method Reference Comment
ΔrH°16.2 ± 1.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Potassium ion (1+) • Toluene) + Toluene = (Potassium ion (1+) • 2Toluene)

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

Quantity Value Units Method Reference Comment
ΔrH°17.9 ± 1.1kcal/molCIDTAmunugama and Rodgers, 2002RCD

(Chromium ion (1+) • Toluene) + Toluene = (Chromium ion (1+) • 2Toluene)

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

Quantity Value Units Method Reference Comment
ΔrH°53.1 ± 9.1kcal/molRAKLin and Dunbar, 1997RCD

Benzene, 1-methyl-3-(1-methylethyl)- + Benzene = Toluene + Benzene, (1-methylethyl)-

By formula: C10H14 + C6H6 = C7H8 + C9H12

Quantity Value Units Method Reference Comment
ΔrH°0.0 ± 0.1kcal/molEqkTsvetkov, Rozhnov, et al., 1985liquid phase; ALS

Lithium ion (1+) + Toluene = (Lithium ion (1+) • Toluene)

By formula: Li+ + C7H8 = (Li+ • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°43.7 ± 4.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

Sodium ion (1+) + Toluene = (Sodium ion (1+) • Toluene)

By formula: Na+ + C7H8 = (Na+ • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°26.8 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

Cesium ion (1+) + Toluene = (Cesium ion (1+) • Toluene)

By formula: Cs+ + C7H8 = (Cs+ • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°15.3 ± 1.1kcal/molCIDTAmunugama and Rodgers, 2002RCD

Rubidium ion (1+) + Toluene = (Rubidium ion (1+) • Toluene)

By formula: Rb+ + C7H8 = (Rb+ • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°17.0 ± 1.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

Potassium ion (1+) + Toluene = (Potassium ion (1+) • Toluene)

By formula: K+ + C7H8 = (K+ • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°19.1 ± 1.2kcal/molCIDTAmunugama and Rodgers, 2002RCD

Chromium ion (1+) + Toluene = (Chromium ion (1+) • Toluene)

By formula: Cr+ + C7H8 = (Cr+ • C7H8)

Quantity Value Units Method Reference Comment
ΔrH°42.1 ± 3.3kcal/molRAKLin and Dunbar, 1997RCD

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

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Owner NIST Mass Spectrometry Data Center
Collection (C) 2014 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin Japan AIST/NIMC Database- Spectrum MS-NW- 67
NIST MS number 227551

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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, Eugeny B. Stern, Antonina A. Goncharova, Natalia A. Messineva, Natalia V. Trusova, Margarita V. Efimkina

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Additional Data

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Source Ramart-Lucas and Bertucat, 1951
Owner INEP CP RAS, NIST OSRD
Collection (C) 2007 copyright by the U.S. Secretary of Commerce
on behalf of the United States of America. All rights reserved.
Origin INSTITUTE OF ENERGY PROBLEMS OF CHEMICAL PHYSICS, RAS
Source reference RAS UV No. 415
Instrument n.i.g.
Melting point -94.9
Boiling point 110.6

References

Go To: Top, Reaction thermochemistry data, Mass spectrum (electron ionization), UV/Visible spectrum, 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]

Kim, Wenthold, et al., 1999
Kim, J.B.; Wenthold, P.G.; Lineberger, W.C., Ultraviolet photoelectron spectroscopy of o-, m-, and p-halobenzyl anions, J. Phys. Chem. A, 1999, 103, 50, 10833-10841, https://doi.org/10.1021/jp992817o . [all data]

Bartmess, Scott, et al., 1979
Bartmess, J.E.; Scott, J.A.; McIver, R.T., Jr., The gas phase acidity scale from methanol to phenol, J. Am. Chem. Soc., 1979, 101, 6047. [all data]

Gal, Decouzon, et al., 2001
Gal, J.F.; Decouzon, M.; Maria, P.C.; Gonzalez, A.I.; Mo, O.; Yanez, M.; El Chaouch, S.; Guillemin, J.C., Acidity trends in alpha,beta-unsaturated alkanes, silanes, germanes, and stannanes, J. Am. Chem. Soc., 2001, 123, 26, 6353-6359, https://doi.org/10.1021/ja004079j . [all data]

Graul and Squires, 1990
Graul, S.T.; Squires, R.R., Gas-Phase Acidities Derived from Threshold Energies for Activated Reactions, J. Am. Chem. Soc., 1990, 112, 7, 2517, https://doi.org/10.1021/ja00163a007 . [all data]

Bohme and Young, 1971
Bohme, D.K.; Young, L.B., Electron affinities from thermal proton transfer reactions: C6H5 and C6H5CH2, Can. J. Chem., 1971, 49, 2918. [all data]

Stone and Stone, 1991
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]

Wojtyniak and Stone, 1986
Wojtyniak, A.C.M.; Stone, A.J., A High-Pressure Mass Spectrometric Study of the Bonding of Trimethylsilylium to Oxygen and Aromatic Bases, Can. J. Chem., 1986, 74, 59. [all data]

Paul and Kebarle, 1991
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]

Ernstberger, Krause, et al., 1990
Ernstberger, B.; Krause, H.; Kiermeier, A.; Neusser, H.J., Multiphoton ionization and dissociation of mixed van der Waals clusters in a linear reflectron time-of-flight mass spectrometer, J. Chem. Phys., 1990, 92, 9, 5285, https://doi.org/10.1063/1.458603 . [all data]

Ruhl, Bisling, et al., 1986
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]

Meot-Ner (Mautner), Hamlet, et al., 1978
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
Meot-Ner (Mautner), M.; El-Shall, M.S., Ionic Charge Transfer Complexes. 1. Cationic Complexes with Delocalized and Partially Localized pi Systems, J. Am. Chem. Soc., 1986, 108, 15, 4386, https://doi.org/10.1021/ja00275a026 . [all data]

Reents and Freiser, 1981
Reents, W.D.; Freiser, B.S., Gas-Phase Binding Energies and Spectroscopic Properties of NO+ Charge-Transfer Complexes, J. Am. Chem. Soc., 1981, 103, 2791. [all data]

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]

Benson and Buss, 1957
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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

French, Ikuta, et al., 1982
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]

Graham, Nichol, et al., 1955
Graham, W.S.; Nichol, R.J.; Ubbelohde, A.R., A thermochemical evaluation of bond strengths in some carbon compounds. Part III. Bond strengths based on the reactions: (a) Ph·CH2I + HI=Ph·CH3 + I2 and (b) PhI + HI=PhH + I2, J. Chem. Soc., 1955, 115-121. [all data]

Ashcroft, Carson, et al., 1963
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]

Caldwell, Masucci, et al., 1989
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]

Tsvetkov, Rozhnov, et al., 1985
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]

Ramart-Lucas and Bertucat, 1951
Ramart-Lucas, Ml; Bertucat, S., Deformation de la structure electronique du carbone par effet sterique (serie de la pyridine), Bull. Soc. Chim. Fr., 1951, 18, 212-214. [all data]

Notes

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