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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Gas phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°gas | 127.3 ± 1.3 | kJ/mol | Eqk | Walsh, Golden, et al., 1966 |
Condensed phase 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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔfH°liquid | 53. ± 2. | kJ/mol | Chyd | Ashcroft, Carson, et al., 1963 |
Phase change 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:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| Tfus | 297.6 | K | N/A | Buckingham and Donaghy, 1982 | BS |
| Tfus | 299.45 | K | N/A | Ashcroft, 1976 | Uncertainty assigned by TRC = 0.5 K; TRC |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔvapH° | 57.4 ± 0.3 | kJ/mol | GS | Krasnykh, Vasiltsova, et al., 2002 | Based on data from 301. to 337. K.; AC |
| ΔvapH° | 57.7 | kJ/mol | CGC | Krasnykh, Vasiltsova, et al., 2002 | AC |
| ΔvapH° | 50.6 ± 1.4 | kJ/mol | N/A | Ashcroft, 1976, 2 | AC |
Reduced pressure boiling point
| Tboil (K) | Pressure (bar) | Reference | Comment |
|---|---|---|---|
| 366.2 | 0.013 | Weast and Grasselli, 1989 | BS |
| 366. | 0.013 | Buckingham and Donaghy, 1982 | BS |
Enthalpy of vaporization
| ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
|---|---|---|---|---|
| 46.8 | 375. | I,A | Stephenson and Malanowski, 1987 | Based on data from 360. to 400. K. See also Ashcroft, 1976, 2.; AC |
Enthalpy of fusion
| ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
|---|---|---|---|
| 13.2 | 299.5 | Ashcroft, 1976, 2 | AC |
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
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° | 1556. ± 8.8 | kJ/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; between tBuCH(Me)OH, FCH2CH2OH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1525. ± 8.4 | kJ/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° | -63.2 ± 3.8 | kJ/mol | RSC | Toscano, Seligson, et al., 1989 | solvent: 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) + (solution) = C8H5IMoO3 (solution) +
(solution)
By formula: C15H12MoO3 (solution) + I2 (solution) = C8H5IMoO3 (solution) + C7H7I (solution)
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -120.5 ± 4.2 | kJ/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° | -33. ± 4.6 | kJ/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° | -12.6 | kJ/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° | -41. ± 2. | kJ/mol | Chyd | Ashcroft, Carson, et al., 1963 | liquid phase; ALS |
IR 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: NIST Mass Spectrometry Data Center, William E. Wallace, director
Gas Phase Spectrum
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Additional Data
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| Owner | NIST Standard Reference Data Program Collection (C) 2018 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
|---|---|
| Origin | NIST Mass Spectrometry Data Center |
| State | gas |
| Instrument | HP-GC/MS/IRD |
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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Due to licensing restrictions, this spectrum cannot be downloaded.
| 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 | ALPHA Chemicals / NIST MS Data Center. |
| NIST MS number | 125335 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Walsh, Golden, et al., 1966
Walsh, R.; Golden, D.M.; Benson, S.W.,
The thermochemistry of the Gas Phase Equilibrium I2 + C6H5CH3 = C6H5CH2I + HI and the heat of formation of the benzyl radical,
J. Am. Chem. Soc., 1966, 88, 650-656. [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]
Buckingham and Donaghy, 1982
Buckingham, J.; Donaghy, S.M.,
Dictionary of Organic Compounds: Fifth Edition, Chapman and Hall, New York, 1982, 1. [all data]
Ashcroft, 1976
Ashcroft, S.J.,
J. Chem. Eng. Data, 1976, 21, 397. [all data]
Krasnykh, Vasiltsova, et al., 2002
Krasnykh, Eugen L.; Vasiltsova, Tatiana V.; Verevkin, Sergey P.; Heintz, Andreas,
Vapor Pressures and Enthalpies of Vaporization of Benzyl Halides and Benzyl Ethers,
J. Chem. Eng. Data, 2002, 47, 6, 1372-1378, https://doi.org/10.1021/je020034h
. [all data]
Ashcroft, 1976, 2
Ashcroft, Stanley J.,
Vapor pressures and enthalpies of vaporization of benzyl halides,
J. Chem. Eng. Data, 1976, 21, 4, 397-398, https://doi.org/10.1021/je60071a009
. [all data]
Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]
Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw,
Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2
. [all data]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Mass spectrum (electron ionization), References
- Symbols used in this document:
Tboil Boiling point Tfus Fusion (melting) point ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid at standard conditions ΔfusH Enthalpy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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