Benzene, (iodomethyl)-
- Formula: C7H7I
- Molecular weight: 218.0350
- IUPAC Standard InChI: InChI=1S/C7H7I/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
- IUPAC Standard InChIKey: XJTQJERLRPWUGL-UHFFFAOYSA-N
- CAS Registry Number: 620-05-3
- 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. - Other names: Toluene, α-iodo-; α-Iodotoluene; (Iodomethyl)benzene; Benzyl iodide; Iodophenylmethane; UN 2653; Fraissite
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Reaction thermochemistry data
Go To: Top, 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
MS - José A. Martinho Simões
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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
C7H6I- + =
By formula: C7H6I- + H+ = C7H7I
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 371.8 ± 2.1 | kcal/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; between tBuCH(Me)OH, FCH2CH2OH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 364.5 ± 2.0 | kcal/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; between tBuCH(Me)OH, FCH2CH2OH; B |
C20H26CoN5O4 (solution) + (solution) = C13H19CoIN5O4 (solution) +
(solution)
By formula: C20H26CoN5O4 (solution) + I2 (solution) = C13H19CoIN5O4 (solution) + C7H7I (solution)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -15.1 ± 0.91 | kcal/mol | RSC | Toscano, Seligson, et al., 1989 | solvent: Bromoform; The enthalpy of solution of Co(py)(dmg)2(Bz)(cr) was measured as 2.70 kcal/mol Toscano, Seligson, et al., 1989; MS |
C15H12MoO3 (solution) + (solution) = C8H5IMoO3 (solution) +
(solution)
By formula: C15H12MoO3 (solution) + I2 (solution) = C8H5IMoO3 (solution) + C7H7I (solution)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -28.8 ± 1.0 | kcal/mol | RSC | Nolan, de la Vega, et al., 1988 | solvent: Tetrahydrofuran; MS |
+
=
+
By formula: HI + C7H7I = C7H8 + I2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -7.8 ± 1.1 | kcal/mol | Cm | Graham, Nichol, et al., 1955 | liquid phase; solvent: p-Xylene; ALS |
+
=
+
By formula: C7H7I + H2O = HI + C7H8O
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -3.00 | kcal/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrolysis; ALS |
=
+ 0.5
By formula: C7H7I = C7H8 + 0.5I2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -9.7 ± 0.4 | kcal/mol | Chyd | Ashcroft, Carson, et al., 1963 | liquid phase; ALS |
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.
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
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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