Benzene, chloro-

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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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
BS - Robert L. Brown and Stephen E. Stein
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
Tboil404.9 ± 0.6KAVGN/AAverage of 53 out of 55 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus228.0 ± 0.4KAVGN/AAverage of 19 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple227.9KN/AStull, 1937Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tc632.35KN/AYoung, 1910Uncertainty assigned by TRC = 0.3 K; disappearance of meniscus; TRC
Tc632.65KN/ALivingston, Morgan, et al., 1908Uncertainty assigned by TRC = 6. K; calculation based on extrap. of density and surface tension; TRC
Tc635.35KN/AAltschul, 1893Uncertainty assigned by TRC = 2. K; disappearance of meniscus; TRC
Quantity Value Units Method Reference Comment
Pc45.191barN/AYoung, 1910Uncertainty assigned by TRC = 0.3039 bar; TRC
Quantity Value Units Method Reference Comment
ρc3.24mol/lN/AYoung, 1910Uncertainty assigned by TRC = 0.04 mol/l; law of rectilinear diam.; TRC
Quantity Value Units Method Reference Comment
Δvap41. ± 4.kJ/molAVGN/AAverage of 7 values; Individual data points

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
35.19404.9N/AMajer and Svoboda, 1985 
48.1258. to 313.GCLiu and Dickhut, 1994AC
35.4420.AStephenson and Malanowski, 1987Based on data from 405. to 597. K.; AC
38.8348.AStephenson and Malanowski, 1987Based on data from 333. to 405. K. See also Brown, 1952 and Boublik, Fried, et al., 1984.; AC
37.3278.MEZibberman-Granovskaya, 1940Based on data from 253. 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
335.19 to 404.884.110831435.675-55.124Brown, 1952, 2Coefficents calculated by NIST from author's data.

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Reference Comment
9.55227.9Domalski and Hearing, 1996AC
9.556227.89Stull, 1937, 2DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
41.93227.89Stull, 1937, 2DH

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
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
LL - Sharon G. Lias and Joel F. Liebman

View reactions leading to C6H5Cl+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
IE (evaluated)9.07 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Proton affinity (review)753.1kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity724.6kJ/molN/AHunter and Lias, 1998HL

Ionization energy determinations

IE (eV) Method Reference Comment
9.08PEFujisawa, Ohno, et al., 1986LBLHLM
8.8PEKlasinc, Kovac, et al., 1983LBLHLM
9.07 ± 0.03PERuscic, Klasinc, et al., 1981LLK
9.10PEKimura, Katsumata, et al., 1981LLK
9.10 ± 0.02PEMohraz, Maier, et al., 1980LLK
9.10 ± 0.02PEMaier and Marthaler, 1978LLK
9.059 ± 0.008EQLias and Ausloos, 1978LLK
9.09PEBehan, Johnstone, et al., 1976LLK
9.55EIBaldwin, Loudon, et al., 1976LLK
9.07 ± 0.02PIPECOBaer, Tsai, et al., 1976LLK
9.1 ± 0.1EIGilbert, Leach, et al., 1973LLK
8.99EICooks, Bertrand, et al., 1973LLK
9.08 ± 0.01PISergeev, Akopyan, et al., 1970RDSH
9.035PIMomigny, Goffart, et al., 1968RDSH
9.05SQuemerais, Morlais, et al., 1967RDSH
9.07PIBralsford, Harris, et al., 1960RDSH
9.07 ± 0.02PIWatanabe, 1957RDSH
9.07PEKlasinc, Kovac, et al., 1983Vertical value; LBLHLM
9.067PEPotts, Lyus, et al., 1980Vertical value; LLK
9.08PESell and Kupperman, 1978Vertical value; LLK
9.07PEKlasinc, Novak, et al., 1978Vertical value; LLK
9.09PEStreets and Ceasar, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C4H4+17.6 ± 0.1?EIMomigny, 1959RDSH
C6H4+14.9 ± 0.2HClEIMomigny, 1959RDSH
C6H5+11.81ClDERRipoche, Dimicoli, et al., 1991LL
C6H5+12.88 ± 0.05ClEIBurgers and Holmes, 1984LBLHLM
C6H5+13.1 ± 0.1ClEIBurgers and Holmes, 1984LBLHLM
C6H5+12.25 ± 0.04ClPIPECORosenstock, Stockbauer, et al., 1980LLK
C6H5+12.47 ± 0.06ClPIRosenstock, Stockbauer, et al., 1979LLK
C6H5+13.06ClPIPECOBaer, Tsai, et al., 1976LLK
C6H5+12.81ClEIJohnstone and Mellon, 1972LLK
C6H5+12.55 ± 0.07ClPISergeev, Akopyan, et al., 1970RDSH
C6H5+13.2 ± 0.1ClEIMajer and Patrick, 1962RDSH

De-protonation reactions

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Δr1636. ± 7.9kJ/molBranWenthold and Squires, 1995gas phase; B
Δr1633. ± 8.8kJ/molG+TSWenthold and Squires, 1994gas phase; between furan, pyridine; B
Δr1633. ± 8.8kJ/molG+TSWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity Value Units Method Reference Comment
Δr1602. ± 8.4kJ/molH-TSWenthold and Squires, 1995gas phase; B
Δr1598. ± 8.4kJ/molIMRBWenthold and Squires, 1994gas phase; between furan, pyridine; B
Δr1598. ± 8.4kJ/molIMRBWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Δr1650. ± 5.4kJ/molBranWenthold and Squires, 1995gas phase; B
Δr1631. ± 8.8kJ/molG+TSWenthold and Squires, 1994gas phase; between furan, pyridine; B
Δr1631. ± 8.8kJ/molG+TSWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B
Quantity Value Units Method Reference Comment
Δr1618. ± 5.9kJ/molH-TSWenthold and Squires, 1995gas phase; B
Δr1598. ± 8.4kJ/molIMRBWenthold and Squires, 1994gas phase; between furan, pyridine; B
Δr1598. ± 8.4kJ/molIMRBWenthold, Paulino, et al., 1991gas phase; Between H2O, furan. Wenthold and Squires, 1994 indicates isomerization occuring.; B

C6H4Cl- + Hydrogen cation = Benzene, chloro-

By formula: C6H4Cl- + H+ = C6H5Cl

Quantity Value Units Method Reference Comment
Δr1618. ± 8.8kJ/molG+TSAndrade and Riveros, 1996gas phase; B
Δr1624. ± 8.4kJ/molBranWenthold and Squires, 1995gas phase; B
Δr1622. ± 13.kJ/molG+TSWenthold, Paulino, et al., 1991gas phase; Between PhF, furan; B
Quantity Value Units Method Reference Comment
Δr1584. ± 8.4kJ/molIMREAndrade and Riveros, 1996gas phase; B
Δr1590. ± 8.8kJ/molH-TSWenthold and Squires, 1995gas phase; B
Δr1588. ± 13.kJ/molIMRBWenthold, Paulino, et al., 1991gas phase; Between PhF, furan; B
Δr1586. ± 21.kJ/molIMRBBartmess and McIver Jr., 1979gas phase; Between H2O, MeOH; B

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.

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]

Young, 1910
Young, S., The Internal Heat of Vaporization constants of thirty pure substances, Sci. Proc. R. Dublin Soc., 1910, 12, 374. [all data]

Livingston, Morgan, et al., 1908
Livingston, J.; Morgan, R.; Higgins, E., The Weight of Falling Drops and Tate's Laws. Determination of Molecular Weights and Critical Temp. of Liquids Using Drop Weights: II., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1908, 64, 170. [all data]

Altschul, 1893
Altschul, M., The critical values of some organic compounds, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1893, 11, 577. [all data]

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Liu and Dickhut, 1994
Liu, Kewen; Dickhut, Rebecca M., Saturation vapor pressures and thermodynamic properties of benzene and selected chlorinated benzenes at environmental temperatures, Chemosphere, 1994, 29, 3, 581-589, https://doi.org/10.1016/0045-6535(94)90445-6 . [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]

Brown, 1952
Brown, I., Aust. J. Sci. Res., Ser. A, 1952, 5, 530. [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]

Zibberman-Granovskaya, 1940
Zibberman-Granovskaya, A.A., Russ. J. Phys. Chem., 1940, 14, 759. [all data]

Brown, 1952, 2
Brown, I., Liquid-Vapour Equilibria. III. The Systems Benzene-n-Heptane, n-Hexane-Chlorobenzene, and cycloHexane-Nitrobenzene, Aust. J. Sci. Res. Ser. A:, 1952, 5, 530-540. [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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [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]

Ruscic, Klasinc, et al., 1981
Ruscic, B.; Klasinc, L.; Wolf, A.; Knop, J.V., Photoelectron spectra of and Ab initio calculations on chlorobenzenes. 1. Chlorobenzene and dichlorobenzenes, J. Phys. Chem., 1981, 85, 1486. [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]

Mohraz, Maier, et al., 1980
Mohraz, M.; Maier, J.P.; Heilbronner, E., He(I α) and He(Iα) photoelectron spectra of fluorinated chloro- and bromobenzenes, J. Electron Spectrosc. Relat. Phenom., 1980, 19, 429. [all data]

Maier and Marthaler, 1978
Maier, J.P.; Marthaler, O., Emission spectra of the radical cations of 1,3-dichlorobenzene, 1,4-dichlorobenzene and 1,3,5-trichlorobenzene in the gas phase, Chem. Phys., 1978, 32, 419. [all data]

Lias and Ausloos, 1978
Lias, S.G.; Ausloos, P.J., eIonization energies of organic compounds by equilibrium measurements, J. Am. Chem. Soc., 1978, 100, 6027. [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]

Gilbert, Leach, et al., 1973
Gilbert, J.R.; Leach, W.P.; Miller, J.R., Ionisation appearance potential measurements in arene chromium tricarbonyls, J. Organomet. Chem., 1973, 49, 219. [all data]

Cooks, Bertrand, et al., 1973
Cooks, R.G.; Bertrand, M.; Beynon, J.H.; Rennekamp, M.E.; Setser, D.W., Energy partitioning data as an ion structure probe. Substituted anisoles, J. Am. Chem. Soc., 1973, 95, 1732. [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]

Quemerais, Morlais, et al., 1967
Quemerais, A.; Morlais, M.; Robin, S., Spectres d'absorption du benzene et du monochlorobenzene dans l'ultraviolet de 1300 a 2300 A, Compt. Rend., 1967, 265, 649. [all data]

Bralsford, Harris, et al., 1960
Bralsford, R.; Harris, P.V.; Price, W.C., The effect of fluorine on the electronic spectra and ionization potentials of molecules, Proc. Roy. Soc. (London), 1960, A258, 459. [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]

Klasinc, Novak, et al., 1978
Klasinc, L.; Novak, I.; Scholz, M.; Kluge, G., Photoelektronenspektren substituierter Pyridine und Benzole und ihre Interpretation durch die CNDO/SWW-Methode, Croat. Chem. Acta, 1978, 51, 43. [all data]

Streets and Ceasar, 1973
Streets, D.G.; Ceasar, G.P., Inductive mesomeric effects on the π orbitals of halobenzenes, Mol. Phys., 1973, 26, 1037. [all data]

Momigny, 1959
Momigny, J., Determination et discussion des potentials d'apparition d'ions fragmentaires dans le benzene et ses derives monohalogenes, Bull. Soc. Roy. Sci. Liege, 1959, 28, 251. [all data]

Ripoche, Dimicoli, et al., 1991
Ripoche, X.; Dimicoli, I.; Botter, R., Unimolecular decay rates for laser induced Cl loss from energy selected chlorobenzene cations [Eo(C6H5Cl+ Ü C6H5+ + Cl)=2.74±0.02 eV; cited data derived using recommended IP for chlorobenzene.], Int. J. Mass Spectrom. Ion Processes, 1991, 107, 165. [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]

Rosenstock, Stockbauer, et al., 1980
Rosenstock, H.M.; Stockbauer, R.; Parr, A.C., Photoelectron-photoion coincidence study of the bromobenzene ion, J. Chem. Phys., 1980, 73, 773. [all data]

Rosenstock, Stockbauer, et al., 1979
Rosenstock, H.M.; Stockbauer, R.; Parr, A.C., Kinetic shift in chlorobenzene ion fragmentation and the heat of formation of the phenyl ion, J. Chem. Phys., 1979, 71, 3708. [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]

Majer and Patrick, 1962
Majer, J.R.; Patrick, C.R., Electron impact on some halogenated aromatic compounds, J. Chem. Soc. Faraday Trans., 1962, 58, 17. [all data]

Wenthold and Squires, 1995
Wenthold, P.G.; Squires, R.R., Determination of the gas-phase acidities of halogen-substituted aromatic compounds using the silane-cleavage method, J. Mass Spectrom., 1995, 30, 1, 17, https://doi.org/10.1002/jms.1190300105 . [all data]

Wenthold and Squires, 1994
Wenthold, P.G.; Squires, R.R., Gas-phase properties and reactivity of the acetate radical anion. Determination of the C-H bond strengths in acetic acid and acetate ion, J. Am. Chem. Soc., 1994, 116, 26, 11890, https://doi.org/10.1021/ja00105a032 . [all data]

Wenthold, Paulino, et al., 1991
Wenthold, P.G.; Paulino, J.A.; Squires, R.R., The Absolute Heats of Formation of ortho-Benzyne, meta-Benzyne, and para-Benzyne, J. Am. Chem. Soc., 1991, 113, 19, 7414, https://doi.org/10.1021/ja00019a044 . [all data]

Andrade and Riveros, 1996
Andrade, P.B.M.; Riveros, J.M., Relative Gas-phase Acidities of Fluoro- and Chlorobenzene, J. Mass Spectrom., 1996, 31, 7, 767, https://doi.org/10.1002/(SICI)1096-9888(199607)31:7<767::AID-JMS345>3.0.CO;2-Q . [all data]

Bartmess and McIver Jr., 1979
Bartmess, J.E.; McIver Jr., The Gas Phase Acidity Scale in Gas Phase Ion Chemistry, Gas Phase Ion Chemistry, V. 2, M.T. Bowers, Ed., Academic Press, NY, 1979, Ch. 11, Elsevier, 1979. [all data]


Notes

Go To: Top, Phase change data, Gas phase ion energetics data, References