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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
Deltar382.33 ± 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
Deltar380.8 ± 2.1kcal/molG+TSBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar379.2 ± 2.1kcal/molG+TSGal, Decouzon, et al., 2001gas phase; B
Deltar377.0 ± 3.5kcal/molCIDTGraul and Squires, 1990gas phase; B
Deltar384.5 ± 7.1kcal/molG+TSBohme and Young, 1971gas phase; B
Quantity Value Units Method Reference Comment
Deltar373.7 ± 2.0kcal/molIMREBartmess, Scott, et al., 1979gas phase; value altered from reference due to change in acidity scale; B
Deltar372.1 ± 2.0kcal/molIMREGal, Decouzon, et al., 2001gas phase; B
Deltar377.4 ± 7.0kcal/molIMRBBohme and Young, 1971gas phase; B

C3H9Si+ + Toluene = (C3H9Si+ bullet Toluene)

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

Quantity Value Units Method Reference Comment
Deltar28.4kcal/molPHPMSStone and Stone, 1991gas phase; forms pi complex; M
Deltar31.3kcal/molPHPMSStone and Stone, 1991gas phase; toluene D8, forms pi complex; M
Deltar26.6kcal/molPHPMSWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H6, Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar34.9cal/mol*KN/AWojtyniak and Stone, 1986gas phase; switching reaction,Thermochemical ladder((CH3)3Si+)C6H6, Entropy change calculated or estimated; M

Free energy of reaction

DeltarG° (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 bullet Toluene)

By formula: Br- + C7H8 = (Br- bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar8.6 ± 1.8kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B,M
Quantity Value Units Method Reference Comment
Deltar20.cal/mol*KN/APaul and Kebarle, 1991gas phase; Entropy change calculated or estimated; M
Quantity Value Units Method Reference Comment
Deltar0.1 ± 1.0kcal/molIMREPaul and Kebarle, 1991gas phase; «DELTA»Gaff measured at 303 K, corrected to 423 K, «DELTA»Saff taken as that of PhNO2..Br-; B

Free energy of reaction

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

C4H9+ + Toluene = (C4H9+ bullet Toluene)

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

Quantity Value Units Method Reference Comment
Deltar28.6kcal/molPHPMSStone and Stone, 1991gas phase; toluene D8, forms protonated t-butyltoluene; M
Deltar29.1kcal/molPHPMSStone and Stone, 1991gas phase; forms protomated t-butyltoluene; M
Quantity Value Units Method Reference Comment
Deltar54.5cal/mol*KPHPMSStone and Stone, 1991gas phase; toluene D8, forms protonated t-butyltoluene; M
Deltar54.6cal/mol*KPHPMSStone and Stone, 1991gas phase; forms protomated t-butyltoluene; M

C7H8+ + Toluene = (C7H8+ bullet Toluene)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar14.5kcal/molMPIErnstberger, Krause, et al., 1990gas phase; M
Deltar5.4kcal/molPIRuhl, Bisling, et al., 1986gas phase; from vIP of perpendicular dimer; M
Deltar16.0kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
Deltar29.cal/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

C6H7N+ + Toluene = (C6H7N+ bullet Toluene)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar13.7kcal/molPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M
Quantity Value Units Method Reference Comment
Deltar26.0cal/mol*KPHPMSMeot-Ner (Mautner) and El-Shall, 1986gas phase; M

C9H12+ + Toluene = (C9H12+ bullet Toluene)

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

Bond type: Charge transfer bond (positive ion)

Quantity Value Units Method Reference Comment
Deltar12.0kcal/molPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M
Quantity Value Units Method Reference Comment
Deltar27.cal/mol*KPHPMSMeot-Ner (Mautner), Hamlet, et al., 1978gas phase; M

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

By formula: NO- + C7H8 = (NO- bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar44.2kcal/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
Deltar8.1 ± 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 bullet Toluene)

By formula: Cl- + C7H8 = (Cl- bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar4.00kcal/molTDEqFrench, Ikuta, et al., 1982gas phase; B

Free energy of reaction

DeltarG° (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
Deltar-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
Deltar-0.9 ± 0.5kcal/molChydAshcroft, Carson, et al., 1963liquid phase; ALS

Iodide + Toluene = (Iodide bullet Toluene)

By formula: I- + C7H8 = (I- bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar11.0 ± 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
Deltar-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
Deltar-9.7 ± 0.4kcal/molChydAshcroft, Carson, et al., 1963liquid phase; ALS

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

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

Quantity Value Units Method Reference Comment
Deltar27.8 ± 0.7kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar20.7 ± 0.5kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar14.7 ± 1.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar16.2 ± 1.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar17.9 ± 1.1kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

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

Quantity Value Units Method Reference Comment
Deltar53.1 ± 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
Deltar0.0 ± 0.1kcal/molEqkTsvetkov, Rozhnov, et al., 1985liquid phase; ALS

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

By formula: Li+ + C7H8 = (Li+ bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar43.7 ± 4.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: Na+ + C7H8 = (Na+ bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar26.8 ± 0.8kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: Cs+ + C7H8 = (Cs+ bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar15.3 ± 1.1kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: Rb+ + C7H8 = (Rb+ bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar17.0 ± 1.0kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: K+ + C7H8 = (K+ bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar19.1 ± 1.2kcal/molCIDTAmunugama and Rodgers, 2002RCD

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

By formula: Cr+ + C7H8 = (Cr+ bullet C7H8)

Quantity Value Units Method Reference Comment
Deltar42.1 ± 3.3kcal/molRAKLin and Dunbar, 1997RCD

References

Go To: Top, Reaction thermochemistry 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]

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]


Notes

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