Benzene, iodo-
- Formula: C6H5I
- Molecular weight: 204.0084
- IUPAC Standard InChIKey: SNHMUERNLJLMHN-UHFFFAOYSA-N
- CAS Registry Number: 591-50-4
- 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: Benzene iodide; Iodobenzene; Phenyl iodide
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Phase change data
Go To: Top, Gas phase ion energetics data, 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:
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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 461.4 ± 0.6 | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 242.15 | K | N/A | Mallikarjun and Hill, 1965 | Uncertainty assigned by TRC = 1. K; TRC |
Tfus | 241.9 | K | N/A | Dreisbach, 1955 | Uncertainty assigned by TRC = 0.02 K; TRC |
Tfus | 241.8 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.3 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 241.8 | K | N/A | Stull, 1937 | Uncertainty assigned by TRC = 0.25 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 47.4 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 313. to 353. K.; AC |
ΔvapH° | 48.9 | kJ/mol | N/A | Boublik, Fried, et al., 1984 | Based on data from 320. to 460. K. See also Basarová and Svoboda, 1991.; AC |
ΔvapH° | 47.7 ± 4.2 | kJ/mol | V | Smith, 1956 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
41.1 | 477. | A | Stephenson and Malanowski, 1987 | Based on data from 462. to 679. K.; AC |
51.4 | 288. | A | Stephenson and Malanowski, 1987 | Based on data from 273. to 358. K. See also Dykyj, 1972.; AC |
46.0 | 373. | A | Stephenson and Malanowski, 1987 | Based on data from 358. to 543. K. See also Dykyj, 1972.; AC |
43.1 | 243. to 255. | N/A | Jones, 1960 | AC |
40.0 | 275. | ME | Zibberman-Granovskaya, 1940 | Based on data from 248. to 303. K.; AC |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
302.4 to 461.4 | 4.3712 | 1803.466 | -47.933 | Young, 1889 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Reference | Comment |
---|---|---|---|
9.75 | 241.8 | Domalski and Hearing, 1996 | AC |
9.749 | 241.83 | Stull, 1937, 2 | DH |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
40.31 | 241.83 | Stull, 1937, 2 | DH |
Gas phase ion energetics data
Go To: Top, Phase change data, References, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Data evaluated as indicated in comments:
L - Sharon G. Lias
Data compiled as indicated in comments:
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 8.72 ± 0.04 | eV | N/A | N/A | L |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
8.79 | PE | Fujisawa, Ohno, et al., 1986 | LBLHLM |
8.75 | PE | Klasinc, Kovac, et al., 1983 | LBLHLM |
8.685 | PIPECO | Dannacher, Rosenstock, et al., 1983 | LBLHLM |
8.79 | PE | Kimura, Katsumata, et al., 1981 | LLK |
8.70 | PE | Behan, Johnstone, et al., 1976 | LLK |
9.05 | EI | Baldwin, Loudon, et al., 1976 | LLK |
8.77 ± 0.02 | PIPECO | Baer, Tsai, et al., 1976 | LLK |
8.67 | PE | Boschi and Salahub, 1974 | LLK |
8.73 ± 0.01 | PI | Sergeev, Akopyan, et al., 1970 | RDSH |
8.685 | PI | Momigny, Goffart, et al., 1968 | RDSH |
8.73 ± 0.03 | PI | Watanabe, 1957 | RDSH |
8.801 | PE | Potts, Lyus, et al., 1980 | Vertical value; LLK |
8.67 | PE | Sell and Kupperman, 1978 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C6H5+ | 11.07 ± 0.07 | I | PI | Malinovich and Lifshitz, 1986 | LBLHLM |
C6H5+ | 10.6 ± 0.1 | I | TRPI | Lifshitz and Malinovich, 1984 | LBLHLM |
C6H5+ | 10.55 ± 0.01 | I | EI | Gefen and Lifshitz, 1984 | LBLHLM |
C6H5+ | 11.2 ± 0.9 | I | PI | Dunbar and Honovich, 1984 | LBLHLM |
C6H5+ | 11.32 ± 0.05 | I | EI | Burgers and Holmes, 1984 | LBLHLM |
C6H5+ | 11.4 ± 0.1 | I | EI | Burgers and Holmes, 1984 | LBLHLM |
C6H5+ | 11.015 | I | PIPECO | Dannacher, Rosenstock, et al., 1983 | LBLHLM |
C6H5+ | 11.4 ± 0.1 | I | EI | Burgers and Holmes, 1982 | LBLHLM |
C6H5+ | 11.27 | I | PIPECO | Baer, Tsai, et al., 1976 | LLK |
C6H5+ | 11.34 | I | EI | Johnstone and Mellon, 1972 | LLK |
C6H5+ | 11.06 ± 0.04 | I | PI | Sergeev, Akopyan, et al., 1970 | RDSH |
C6H5+ | 11.46 | I | EI | Howe and Williams, 1969 | RDSH |
References
Go To: Top, Phase change data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Mallikarjun and Hill, 1965
Mallikarjun, S.; Hill, N.E.,
Temperature dependence of viscosity and dielectric relaxation time in simple polar liquids,
Trans. Faraday Soc., 1965, 61, 1389. [all data]
Dreisbach, 1955
Dreisbach, R.R.,
Physical Properties of Chemical Compounds, Advances in Chemistry Series No. 15, Am. Chem. Soc.: Washington, D. C., 1955. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [all data]
Stull, 1937
Stull, D.R.,
A Semi-micro Calorimeter for Measuring Heat Capacities at Low Temp.,
J. Am. Chem. Soc., 1937, 59, 2726. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
. [all data]
Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E.,
The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]
Basarová and Svoboda, 1991
Basarová, Pavlína; Svoboda, Václav,
Calculation of heats of vaporization of halogenated hydrocarbons from saturated vapour pressure data,
Fluid Phase Equilibria, 1991, 68, 13-34, https://doi.org/10.1016/0378-3812(91)85008-I
. [all data]
Smith, 1956
Smith, L.,
Corrected heats of combustion of organic iodine compounds,
Acta Chem. Scand., 1956, 10, 884-886. [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]
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]
Dykyj, 1972
Dykyj, J.,
Petrochemia, 1972, 12, 1, 13. [all data]
Jones, 1960
Jones, A.H.,
Sublimation Pressure Data for Organic Compounds.,
J. Chem. Eng. Data, 1960, 5, 2, 196-200, https://doi.org/10.1021/je60006a019
. [all data]
Zibberman-Granovskaya, 1940
Zibberman-Granovskaya, A.A.,
Russ. J. Phys. Chem., 1940, 14, 759. [all data]
Young, 1889
Young, S.,
On the Vapour-Pressures and Specific Volumes of Similar Compounds of Elements in Relation to the Position of those Elements in the Periodic Table,
J. Chem. Soc., 1889, 55, 486-521, https://doi.org/10.1039/ct8895500486
. [all data]
Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D.,
Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III,
J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985
. [all data]
Stull, 1937, 2
Stull, D.R.,
A semi-micro calorimeter for measuring heat capacities at low temperatures,
J. Am. Chem. Soc., 1937, 59, 2726-2733. [all data]
Fujisawa, Ohno, et al., 1986
Fujisawa, S.; Ohno, K.; Masuda, S.; Harada, Y.,
Penning ionization electron spectroscopy of monohalogenobenzenes: C6H5F, C6H5Cl, C6H5Br, and C6H5I,
J. Am. Chem. Soc., 1986, 108, 6505. [all data]
Klasinc, Kovac, et al., 1983
Klasinc, L.; Kovac, B.; Gusten, H.,
Photoelectron spectra of acenes. Electronic structure and substituent effects,
Pure Appl. Chem., 1983, 55, 289. [all data]
Dannacher, Rosenstock, et al., 1983
Dannacher, J.; Rosenstock, H.M.; Buff, R.; Parr, A.C.; Stockbauer, R.L.; Bombach, R.; Stadelmann, J.-P.,
Benchmark measurement of iodobenzene ion fragmentation rates,
Chem. Phys., 1983, 75, 23. [all data]
Kimura, Katsumata, et al., 1981
Kimura, K.; Katsumata, S.; Achiba, Y.; Yamazaki, T.; Iwata, S.,
Ionization energies, Ab initio assignments, and valence electronic structure for 200 molecules
in Handbook of HeI Photoelectron Spectra of Fundamental Organic Compounds, Japan Scientific Soc. Press, Tokyo, 1981. [all data]
Behan, Johnstone, et al., 1976
Behan, J.M.; Johnstone, R.A.W.; Bentley, T.W.,
An evaluation of empirical methods for calculating the ionization potentials of substituted benzenes,
Org. Mass Spectrom., 1976, 11, 207. [all data]
Baldwin, Loudon, et al., 1976
Baldwin, M.A.; Loudon, A.G.; Maccoll, A.; Webb, K.S.,
The nature and fragmentation pathways of the molecular ions of some arylureas, arylthioureas, acetanilides, thioacetanilides and related compounds,
Org. Mass Spectrom., 1976, 11, 1181. [all data]
Baer, Tsai, et al., 1976
Baer, T.; Tsai, B.P.; Smith, D.; Murray, P.T.,
Absolute unimolecular decay rates of energy selected metastable halobenzene ions,
J. Chem. Phys., 1976, 64, 2460. [all data]
Boschi and Salahub, 1974
Boschi, R.A.A.; Salahub, D.R.,
The high resolution photoelectron spectra of some iodoalkanes, iodocycloalkanes, iodoalkenes, and fluoroiodohydrocarbons,
Can. J. Chem., 1974, 52, 1217. [all data]
Sergeev, Akopyan, et al., 1970
Sergeev, Yu.L.; Akopyan, M.E.; Vilesov, F.I.; Kleimenov, V.I.,
Photoionization processes in phenyl halides,
Opt. i Spektroskopiya, 1970, 29, 119, In original 63. [all data]
Momigny, Goffart, et al., 1968
Momigny, J.; Goffart, C.; D'Or, L.,
Photoionization studies by total ionization measurements. I. Benzene and its monohalogeno derivatives,
Intern. J. Mass Spectrom. Ion Phys., 1968, 1, 53. [all data]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Potts, Lyus, et al., 1980
Potts, A.W.; Lyus, M.L.; Lee, E.P.F.; Fattahallah, G.H.,
High resolution ultraviolet photoelectron spectra of C6H5X and p-C6H4X2 where X = Cl, Br or I,
J. Chem. Soc. Faraday Trans. 2, 1980, 76, 556. [all data]
Sell and Kupperman, 1978
Sell, J.A.; Kupperman, A.,
Angular distributions in the photoelectron spectra of benzene and its monohalogenated derivatives,
Chem. Phys., 1978, 33, 367. [all data]
Malinovich and Lifshitz, 1986
Malinovich, Y.; Lifshitz, C.,
Time-dependent mass spectra and breakdown graphs. 7. Time-resolved photoionization mass spectrometry of iodobenzene. The heat of formation of C6H5+,
J. Phys. Chem., 1986, 90, 2200. [all data]
Lifshitz and Malinovich, 1984
Lifshitz, C.; Malinovich, Y.,
Time resolved photoionization mass spectrometry in the millisecond range,
Int. J. Mass Spectrom. Ion Processes, 1984, 60, 99. [all data]
Gefen and Lifshitz, 1984
Gefen, S.; Lifshitz, C.,
Time-dependent mass spectra and breakdown graphs. V. The kinetic shift in iodobenzene,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 251. [all data]
Dunbar and Honovich, 1984
Dunbar, R.C.; Honovich, J.P.,
Threshold ion photodissociation. Bromobenzene and iodobenzene ions,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 25. [all data]
Burgers and Holmes, 1984
Burgers, P.C.; Holmes, J.L.,
Fragmentation rate constants and appearance energies for reactions having a large kinetic shift and the energy partitioning in their metastable decomposition,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 15. [all data]
Burgers and Holmes, 1982
Burgers, P.C.; Holmes, J.L.,
Metastable ion studies. XIII. The measurement of appearance energies of metastable peaks,
Org. Mass Spectrom., 1982, 17, 123. [all data]
Johnstone and Mellon, 1972
Johnstone, R.A.W.; Mellon, F.A.,
Electron-impact ionization and appearance potentials,
J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1209. [all data]
Howe and Williams, 1969
Howe, I.; Williams, D.H.,
Calculation and qualitative predictions of mass spectra. Mono- and paradisubstituted benzenes,
J. Am. Chem. Soc., 1969, 91, 7137. [all data]
Notes
Go To: Top, Phase change data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion 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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