Benzene, (iodomethyl)-
- Formula: C7H7I
- Molecular weight: 218.0350
- 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 |
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 |
Gas phase ion energetics 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
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.73 ± 0.02 | PI | Traeger and Kompe, 1990 | LL |
8.8 | EI | Yeo and Williams, 1970 | RDSH |
8.91 | PE | Schmidt and Schweig, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C7H7+ | 8.84 ± 0.02 | I | PI | Traeger and Kompe, 1990 | LL |
C7H7+ | 9.2 | I | EI | Yeo and Williams, 1970 | RDSH |
De-protonation 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 |
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 |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, 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]
Traeger and Kompe, 1990
Traeger, J.C.; Kompe, B.M.,
Threshold C7H7 formation from the benzyl halides by photoionization mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1990, 101, 111. [all data]
Yeo and Williams, 1970
Yeo, A.N.H.; Williams, D.H.,
Rearrangement in the molecular ions of halogenotoluenes prior to fragmentation in the mass spectrometer,
Chem. Commun., 1970, 886. [all data]
Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A.,
C-Hal hyperkonjugation,
Tetrahedron Lett., 1973, 981. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, References
- Symbols used in this document:
AE Appearance energy 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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