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Benzene, (iodomethyl)-

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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 - J.E. Bartmess
MS - J.A. Martinho Simões
ALS - H.Y. Afeefy, J.F. Liebman, and S.E. Stein

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Individual Reactions

C7H6I- + Hydrogen cation = Benzene, (iodomethyl)-

By formula: C7H6I- + H+ = C7H7I

Quantity Value Units Method Reference Comment
Deltar1556. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; between tBuCH(Me)OH, FCH2CH2OH; B
Quantity Value Units Method Reference Comment
Deltar1525. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; between tBuCH(Me)OH, FCH2CH2OH; B

C20H26CoN5O4 (solution) + Iodine (solution) = C13H19CoIN5O4 (solution) + Benzene, (iodomethyl)- (solution)

By formula: C20H26CoN5O4 (solution) + I2 (solution) = C13H19CoIN5O4 (solution) + C7H7I (solution)

Quantity Value Units Method Reference Comment
Deltar-63.2 ± 3.8kJ/molRSCToscano, Seligson, et al., 1989solvent: Bromoform; The enthalpy of solution of Co(py)(dmg)2(Bz)(cr) was measured as 11.3 kJ/mol Toscano, Seligson, et al., 1989; MS

C15H12MoO3 (solution) + Iodine (solution) = C8H5IMoO3 (solution) + Benzene, (iodomethyl)- (solution)

By formula: C15H12MoO3 (solution) + I2 (solution) = C8H5IMoO3 (solution) + C7H7I (solution)

Quantity Value Units Method Reference Comment
Deltar-120.5 ± 4.2kJ/molRSCNolan, de la Vega, et al., 1988solvent: Tetrahydrofuran; MS

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

By formula: HI + C7H7I = C7H8 + I2

Quantity Value Units Method Reference Comment
Deltar-33. ± 4.6kJ/molCmGraham, Nichol, et al., 1955liquid phase; solvent: p-Xylene; ALS

Benzene, (iodomethyl)- + Water = Hydrogen iodide + Benzyl alcohol

By formula: C7H7I + H2O = HI + C7H8O

Quantity Value Units Method Reference Comment
Deltar-12.6kJ/molCmGellner and Skinner, 1949liquid phase; Heat of hydrolysis; ALS

Benzene, (iodomethyl)- = Toluene + 0.5Iodine

By formula: C7H7I = C7H8 + 0.5I2

Quantity Value Units Method Reference Comment
Deltar-41. ± 2.kJ/molChydAshcroft, Carson, et al., 1963liquid phase; ALS

References

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

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Toscano, Seligson, et al., 1989
Toscano, P.J.; Seligson, A.L.; Curran, M.T.; Skrobutt, A.T.; Sonnenberger, D.C., Inorg. Chem., 1989, 28, 166; ibid. 1989. [all data]

Nolan, de la Vega, et al., 1988
Nolan, S.P.; de la Vega, R.L.; Mukerjee, S.L.; Gonzalez, A.A.; Zhang, K.; Hoff, C., Polyhedron, 1988, 7, 1491. [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]

Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A., Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X, J. Chem. Soc., 1949, 1145-1148. [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]


Notes

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