Benzene, 1,4-dichloro-

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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 as indicated in comments:
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
Δcliquid-2937. ± 4.kJ/molCcbSmith, Bjellerup, et al., 1953ALS
Quantity Value Units Method Reference Comment
Δfsolid-42.3 ± 1.0kJ/molCcbHubbard, Knowlton, et al., 1954ALS
Quantity Value Units Method Reference Comment
Δcsolid-2939.9kJ/molCcrPlatonov and Simulin, 1984ALS
Δcsolid-2934.1 ± 1.0kJ/molCcbHubbard, Knowlton, et al., 1954ALS
Quantity Value Units Method Reference Comment
solid,1 bar175.41J/mol*KN/ADworkin, Figuiere, et al., 1976crystaline, II phase; DH

Constant pressure heat capacity of solid

Cp,solid (J/mol*K) Temperature (K) Reference Comment
98.180.Martin and Monti, 1988T = 30 to 180 K. Data given graphically, and estimated from graph.; DH
147.76298.15Dworkin, Figuiere, et al., 1976crystaline, II phase; T = 20 to 330 K.; DH
142.7298.15Ueberreiter and Orthmann, 1950T = 293 to 368 K. Equation only.; DH
172.0299.8Andrews and Haworth, 1928T = 101 to 336 K. Value is unsmoothed experimental datum.; DH
147.6298.Narbutt, 1918T = 194 to 372 K. Average specific heat over the temperature range 2.6 to 51.6 °C is 0.2400 cal/g*K.; DH

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
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
Tboil447.3 ± 0.6KAVGN/AAverage of 6 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus326.1 ± 0.8KAVGN/AAverage of 26 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple326.150KN/ADworkin, Figuiere, et al., 1976, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.01 K; TRC
Quantity Value Units Method Reference Comment
Δvap54.8kJ/molGCSpieksma, Luijk, et al., 1994Based on data from 413. to 453. K.; AC
Δvap47.8kJ/molN/ABoublik, Fried, et al., 1984Based on data from 370. to 450. K. See also Basarová and Svoboda, 1991.; AC
Quantity Value Units Method Reference Comment
Δsub64.75 ± 0.15kJ/molDMOonk, van Genderen, et al., 2000AC
Δsub65.2 ± 2.0kJ/molCAn and Zheng, 1989AC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
46.4326.N/ARohác, Ruzicka, et al., 1999AC
44.2373.EBRohác, Ruzicka, et al., 1998Based on data from 358. to 448. K.; AC
45.0356.AStephenson and Malanowski, 1987Based on data from 341. to 448. K.; AC

Antoine Equation Parameters

log10(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Temperature (K) A B C Reference
341.12 to 447.214.1231575.11-64.637McDonald, Shrader, et al., 1959

Enthalpy of sublimation

ΔsubH (kJ/mol) Temperature (K) Method Reference Comment
53.1258. to 313.N/ALiu and Dickhut, 1994AC
65.4313.GSShaub, 1985Based on data from 303. to 423. K.; AC
64.8 ± 0.4303.VWalsh and Smith, 1961ALS
64.8 ± 0.8303.N/AWalsh and Smith, 1961, 2Based on data from 293. to 311. K. See also Cox and Pilcher, 1970.; AC
63. ± 0.4318.N/AWalsh and Smith, 1961, 2Based on data from 311. to 325. K.; AC
56.9275.MEDarkis, Vermillion, et al., 1940Based on data from 248. to 303. K. See also Jones, 1960.; AC

Enthalpy of fusion

ΔfusH (kJ/mol) Temperature (K) Method Reference Comment
18.19326.2DSCWei and Jin, 2009See also Wei, 2008.; AC
17.91326.2ACvan der Linde, van Miltenburg, et al., 2005Based on data from 5. to 380. K.; AC
18.16326.N/AAcree, 1991AC
18.050326.15N/ABooss and Hauschildt, 1972DH
18.160326.N/AUeberreiter and Orthmann, 1950DH
18.144326.05N/ANarbutt, 1918DH

Entropy of fusion

ΔfusS (J/mol*K) Temperature (K) Reference Comment
55.3326.15Booss and Hauschildt, 1972DH
55.7326.Ueberreiter and Orthmann, 1950DH
55.6326.05Narbutt, 1918DH

Enthalpy of phase transition

ΔHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
0.200304.0crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH
1.256271.77crystaline, IIIcrystaline, IIDworkin, Figuiere, et al., 1976DH
0.2145304.35crystaline, IIcrystaline, IDworkin, Figuiere, et al., 1976DH
18.187326.14crystaline, IliquidDworkin, Figuiere, et al., 1976DH
1.256271.77crystaline, IIIcrystaline, IIDworkin, Figuiere, et al., 1975DH
0.2145304.35crystaline, IIcrystaline, IDworkin, Figuiere, et al., 1975DH
18.187326.14crystaline, IliquidDworkin, Figuiere, et al., 1975DH

Entropy of phase transition

ΔStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
0.6304.0crystaline, IIcrystaline, IPetropavlov, Tsygankova, et al., 1988DH
4.62271.77crystaline, IIIcrystaline, IIDworkin, Figuiere, et al., 1976DH
0.705304.35crystaline, IIcrystaline, IDworkin, Figuiere, et al., 1976DH
55.76326.14crystaline, IliquidDworkin, Figuiere, et al., 1976DH
4.62271.77crystaline, IIIcrystaline, IIDworkin, Figuiere, et al., 1975DH
0.705304.35crystaline, IIcrystaline, IDworkin, Figuiere, et al., 1975DH
55.76326.14crystaline, IliquidDworkin, Figuiere, et al., 1975DH

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:


Henry's Law 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: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.23 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.312700.XN/A 
0.312700.XN/A 
0.382700.XN/A 
0.63 LN/A 
0.42 MN/A 
0.22 VN/A 

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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LL - Sharon G. Lias and Joel F. Liebman
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)8.92 ± 0.03eVN/AN/AL
Quantity Value Units Method Reference Comment
Δf(+) ion883.2kJ/molN/AN/A 
Quantity Value Units Method Reference Comment
ΔfH(+) ion,0K895.8kJ/molN/AN/A 

Ionization energy determinations

IE (eV) Method Reference Comment
8.95PEFujisawa, Oonishi, et al., 1991LL
8.92 ± 0.02PIPECOOlesik, Baer, et al., 1986LBLHLM
8.97 ± 0.03PERuscic, Klasinc, et al., 1981LLK
8.94PEKimura, Katsumata, et al., 1981LLK
8.98 ± 0.02PEMaier and Marthaler, 1978LLK
8.89 ± 0.01EQLias and Ausloos, 1978LLK
8.94 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
8.95PIBralsford, Harris, et al., 1960RDSH
8.988PEPotts, Lyus, et al., 1980Vertical value; LLK
9.00PEStreets and Ceasar, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H4Cl+13.2 ± 0.1ClEIBrown, 1970RDSH

De-protonation reactions

C6H3Cl2- + Hydrogen cation = Benzene, 1,4-dichloro-

By formula: C6H3Cl2- + H+ = C6H4Cl2

Quantity Value Units Method Reference Comment
Δr1577. ± 8.8kJ/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: p-dichlorobenzene.; B
Quantity Value Units Method Reference Comment
Δr1543. ± 8.4kJ/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: p-dichlorobenzene.; B

References

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law 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.

Smith, Bjellerup, et al., 1953
Smith, L.; Bjellerup, L.; Krook, S.; Westermark, H., Heats of combustion of organic chloro compounds determined by the "quartz wool" method, Acta Chem. Scand., 1953, 7, 65. [all data]

Hubbard, Knowlton, et al., 1954
Hubbard, W.N.; Knowlton, J.W.; Huffman, H.M., Combustion calorimetry of organic chlorine compounds. Heats of combustion of chlorobenzene, the dichlorobenzenes and o- and p-chloroethylbenzene, J. Phys. Chem., 1954, 58, 396. [all data]

Platonov and Simulin, 1984
Platonov, V.A.; Simulin, Yu.N., Experimental determination of the standard enthalpies of formation of polychlorobenzenes. II. Standard enthalpies of formation of dichlorobenzenes, Russ. J. Phys. Chem. (Engl. Transl.), 1984, 58, 1630-1632. [all data]

Dworkin, Figuiere, et al., 1976
Dworkin, A.; Figuiere, P.; Ghelfenstein, M.; Szwarc, H., Heat capacities, enthalpies of transition, and thermodynamic properties of the three solid phases of p-dichlorobenzene from 20 to 330 K, J. Chem. Thermodynam., 1976, 8, 835-844. [all data]

Martin and Monti, 1988
Martin, C.A.; Monti, G.A., Dynamical analysis of the specific heat in p-dichlorobenzene, Thermochim. Acta, 1988, 134, 35-39. [all data]

Ueberreiter and Orthmann, 1950
Ueberreiter, K.; Orthmann, H.-J., Specifische Wärme, spezifisches Volumen, Temperatur- und Wärme-leittähigkeit einiger disubstituierter Benzole und polycyclischer Systeme, Z. Natursforsch. 5a, 1950, 101-108. [all data]

Andrews and Haworth, 1928
Andrews, D.H.; Haworth, E., An application of the rule of Dulong and Petit to molecules, J. Am. Chem. Soc., 1928, 50, 2998-3002. [all data]

Narbutt, 1918
Narbutt, J., Die Spezifischen Warmen und Schmelzwarmen der dichloro-, chlorbrom-, dibrom-, bromjod-, und dijodbenzole. I, Z. Elektrochem., 1918, 24, 339-342. [all data]

Dworkin, Figuiere, et al., 1976, 2
Dworkin, A.; Figuiere, P.; Ghelfenstein, M.; Szwarc, H., Heat Capacities, Enthalpies of Transition, and Thermodynamic Properties of the Three Solid Phases of p-Dichlorobenzene from 20 to 330 K, J. Chem. Thermodyn., 1976, 8, 835-44. [all data]

Spieksma, Luijk, et al., 1994
Spieksma, Walter; Luijk, Ronald; Govers, Harrie A.J., Determination of the liquid vapour pressure of low-volatility compounds from the Kováts retention index, Journal of Chromatography A, 1994, 672, 1-2, 141-148, https://doi.org/10.1016/0021-9673(94)80602-0 . [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]

Oonk, van Genderen, et al., 2000
Oonk, Harry A.J.; van Genderen, Aad C.G.; Blok, Jacobus G.; van der Linde, Peter R., Vapour pressures of crystalline and liquid 1,4-dibromo- and 1,4-dichlorobenzene; lattice energies of 1,4-dihalobenzenes, Phys. Chem. Chem. Phys., 2000, 2, 24, 5614-5618, https://doi.org/10.1039/b005324o . [all data]

An and Zheng, 1989
An, Xuwu; Zheng, Xiaolin, Determination of Standard Enthalpies of Vaporization and Sublimation of Three Dichlorobenzenes, Acta Phys. Chim. Sin., 1989, 5, 4, 487-491, https://doi.org/10.3866/PKU.WHXB19890421 . [all data]

Rohác, Ruzicka, et al., 1999
Rohác, Vladislav; Ruzicka, Vlastimil; Ruzicka, Kvetoslav; Polednicek, Milos; Aim, Karel; Jose, Jacques; Zábranský, Milan, Recommended vapour and sublimation pressures and related thermal data for chlorobenzenes, Fluid Phase Equilibria, 1999, 157, 1, 121-142, https://doi.org/10.1016/S0378-3812(99)00003-5 . [all data]

Rohác, Ruzicka, et al., 1998
Rohác, Vladislav; Ruzicka, Vlastimil; Ruzicka, Kvetoslav; Aim, Karel, Measurements of Saturated Vapor Pressure above the Liquid Phase for Isomeric Dichlorobenzenes and 1,2,4-Trichlorobenzene, J. Chem. Eng. Data, 1998, 43, 5, 770-775, https://doi.org/10.1021/je9701442 . [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]

McDonald, Shrader, et al., 1959
McDonald, R.A.; Shrader, S.A.; Stull, D.R., Vapor Pressures and Freezing Points of Thirty Pure Organic Compounds., J. Chem. Eng. Data, 1959, 4, 4, 311-313, https://doi.org/10.1021/je60004a009 . [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]

Shaub, 1985
Shaub, W.M., Containment of dioxin emissions from refuse fired thermal processing units - prospects and technical issues, Thermochimica Acta, 1985, 85, 435-438, https://doi.org/10.1016/0040-6031(85)85614-8 . [all data]

Walsh and Smith, 1961
Walsh, P.N.; Smith, N.O., Sublimation pressure of a-p-dichloro-,β-p-dichloro-, p-dibromo-, and p-bromochlorobenzene, J. Chem. Eng. Data, 1961, 6, 33. [all data]

Walsh and Smith, 1961, 2
Walsh, P.N.; Smith, N.O., Sublimation Pressure of α-p-Dichloro-β-p-Dichloro, and p-Dibromo-, and p-Bromochlorobenzene., J. Chem. Eng. Data, 1961, 6, 1, 33-35, https://doi.org/10.1021/je60009a010 . [all data]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press Inc., London, 1970, 643. [all data]

Darkis, Vermillion, et al., 1940
Darkis, F.R.; Vermillion, H.E.; Gross, P.M., p--Dichlorobenzene as a Vapor Fumigant Physical and Chemical Studies, Ind. Eng. Chem., 1940, 32, 7, 946-949, https://doi.org/10.1021/ie50367a018 . [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]

Wei and Jin, 2009
Wei, Dongwei; Jin, Kexin, (Solid+liquid) equilibria of (naphthalene+isomeric dichlorobenzenes), The Journal of Chemical Thermodynamics, 2009, 41, 2, 145-149, https://doi.org/10.1016/j.jct.2008.10.005 . [all data]

Wei, 2008
Wei, Dongwei, (Solid+liquid) equilibria of (phenanthrene+dichlorobenzenes), Thermochimica Acta, 2008, 479, 1-2, 32-36, https://doi.org/10.1016/j.tca.2008.09.010 . [all data]

van der Linde, van Miltenburg, et al., 2005
van der Linde, Peter R.; van Miltenburg, J. Cees; van den Berg, Gerrit J.K.; Oonk, Harry A.J., Low-Temperature Heat Capacities and Derived Thermodynamic Functions of 1,4-Dichlorobenzene, 1,4-Dibromobenzene, 1,3,5-Trichlorobenzene, and 1,3,5-Tribromobenzene, J. Chem. Eng. Data, 2005, 50, 1, 164-172, https://doi.org/10.1021/je049762q . [all data]

Acree, 1991
Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Booss and Hauschildt, 1972
Booss, H.J.; Hauschildt, K.R., Die Schmelzenthalpie des Benzils und 4-Nitrophenols, Z. Anal. Chem., 1972, 261(1), 32. [all data]

Petropavlov, Tsygankova, et al., 1988
Petropavlov, N.N.; Tsygankova, I.G.; Teslenko, L.A., Microcalorimetric investigation of polymorphic transitions in organic crystals, Sov. Phys. Crystallogr., 1988, 33(6), 853-855. [all data]

Dworkin, Figuiere, et al., 1975
Dworkin, A.; Figuiere, P.; Ghelfenstein, M.; Szwarc, H., Thermodynamic properties of the three solid phases of p-dichlorobenzene, Quatrieme Conference International de Thermodynamique Chimique, 1975, II, Thermophysique (capacites thermiques) pp. [all data]

Fujisawa, Oonishi, et al., 1991
Fujisawa, S.; Oonishi, I.; Masuda, S.; Ohno, K.; Harada, Y., Penning ionization electron spectroscopy of dichlorobenzenes, J. Phys. Chem., 1991, 95, 4250. [all data]

Olesik, Baer, et al., 1986
Olesik, S.; Baer, T.; Morrow, J.C., Dissociation rates of energy-selected dichloro- and dibromobenzene ions, J. Phys. Chem., 1986, 90, 3563. [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]

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]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]

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]

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]

Brown, 1970
Brown, P., Kinetic studies in mass spectrometry-IV. The [M - Cl] reaction in substituted chlorobenzenes and the question of molecular ion isomerization, Org. Mass Spectrom., 1970, 3, 639. [all data]

Schlosser, Marzi, et al., 2001
Schlosser, M.; Marzi, E.; Cottet, F.; Buker, H.H.; Nibbering, N.M.M., The acidity of chloro-substituted benzenes: A comparison of gas phase, ab initio, and kinetic data, Chem. Eur. J., 2001, 7, 16, 3511-3516, https://doi.org/10.1002/1521-3765(20010817)7:16<3511::AID-CHEM3511>3.0.CO;2-U . [all data]


Notes

Go To: Top, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, References