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Benzene, 1,2-dichloro-

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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
Deltafgas33.0kJ/molCcrPlatonov and Simulin, 1984 

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
Deltafliquid-17.4 ± 1.3kJ/molCcbSinke and Stull, 1958Reanalyzed by Cox and Pilcher, 1970, Original value = -18. ± 1. kJ/mol; ALS
Deltafliquid-16. ± 2.kJ/molCcrBjellerup and Smith, 1954At 293 K; ALS
Deltafliquid-17.6 ± 0.71kJ/molCcbHubbard, Knowlton, et al., 1954ALS
Quantity Value Units Method Reference Comment
Deltacliquid-2962. ± 5.kJ/molAVGN/AAverage of 6 values; Individual data points

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
170.9298.15Narbutt, 1918T = 197 to 375 K. Cp = 0.27022 + 0.0003024t cal/g*K. Cp value calculated from equation.; 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, Kenneth Kroenlein director
AC - William E. Acree, Jr., James S. Chickos
DH - Eugene S. Domalski and Elizabeth D. Hearing

Quantity Value Units Method Reference Comment
Tboil453.7KN/AWeast and Grasselli, 1989BS
Tboil453.4KN/AKailuru and Abburi, 1988Uncertainty assigned by TRC = 0.5 K; TRC
Tboil453.KN/AWalling and Miller, 1957Uncertainty assigned by TRC = 1.5 K; TRC
Tboil453.63KN/ADreisbach and Martin, 1949Uncertainty assigned by TRC = 0.07 K; TRC
Tboil452.65KN/ALecat, 1943Uncertainty assigned by TRC = 0.35 K; TRC
Quantity Value Units Method Reference Comment
Tfus256.0 ± 0.6KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Deltavap50.9kJ/molGCSpieksma, Luijk, et al., 1994Based on data from 413. - 453. K.; AC
Deltavap48.5 ± 0.1kJ/molCAn and Zheng, 1989AC
Deltavap49.9kJ/molN/ABoublik, Fried, et al., 1984Based on data from 360. - 450. K. See also Basarová and Svoboda, 1991.; AC

Reduced pressure boiling point

Tboil (K) Pressure (bar) Reference Comment
451.21.02Aldrich Chemical Company Inc., 1990BS

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
50.0322.GSGrayson and Fosbraey, 2006Based on data from 301. - 343. K.; AC
51.2256.N/ARohác, Ruzicka, et al., 1999AC
44.5376.EBRohác, Ruzicka, et al., 1998Based on data from 363. - 454. K.; AC
50.8271.N/APolednicek, Guetachew, et al., 1996Based on data from 256. - 287. K.; AC
51.2258. - 313.GCLiu and Dickhut, 1994AC
44.0388.AStephenson and Malanowski, 1987Based on data from 373. - 453. 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
293.14 - 453.574.195181649.55-59.836McDonald, Shrader, et al., 1959

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
12.4255.9DSCWei and Jin, 2009See also Wei, 2008.; AC
12.93256.5N/AAcree, 1991AC
12.922255.65N/ANarbutt, 1918DH

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
50.5255.65Narbutt, 1918DH

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:


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
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

C6H3Cl2- + Hydrogen cation = Benzene, 1,2-dichloro-

By formula: C6H3Cl2- + H+ = C6H4Cl2

Quantity Value Units Method Reference Comment
Deltar1578. ± 8.8kJ/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.; B
Quantity Value Units Method Reference Comment
Deltar1543. ± 8.4kJ/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.; B

Benzene, 1,4-dichloro- = Benzene, 1,2-dichloro-

By formula: C6H4Cl2 = C6H4Cl2

Quantity Value Units Method Reference Comment
Deltar8.803kJ/molEqkGodnev and Sverdlin, 1961gas phase; Correction of 56GOD/SVE; ALS

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
0.545900.LN/A 
0.33 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.495100.XN/A 
0.531400.XN/A 
0.596700.XN/A 
0.522800.XN/A 
0.53 LN/A 
0.53 MN/A 
0.41 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)9.06 ± 0.02eVN/AN/AL
Quantity Value Units Method Reference Comment
Deltaf(+) ion904.2kJ/molN/AN/A 
Quantity Value Units Method Reference Comment
DeltafH(+) ion,0K916.7kJ/molN/AN/A 

Electron affinity determinations

EA (eV) Method Reference Comment
0.093668ECDSteelhammer and Wentworth, 1969G3MP2B3 calculations indicate an EA of ca. -0.2 eV, unbound.; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.06 ± 0.02PIPECOOlesik, Baer, et al., 1986LBLHLM
9.08 ± 0.03PERuscic, Klasinc, et al., 1981LLK
9.06 ± 0.02PEMaier and Marthaler, 1978LLK
9.08 ± 0.01EQLias and Ausloos, 1978LLK
9.07 ± 0.01PIWatanabe, Nakayama, et al., 1962RDSH
9.06PIBralsford, Harris, et al., 1960RDSH
9.24PEFujisawa, Oonishi, et al., 1991Vertical value; LL
9.23PEKimura, Katsumata, et al., 1981Vertical value; LLK
9.08PEStreets and Ceasar, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C6H4Cl+12.35ClESTTakhistov and Ponomarev, 1994LL
C6H4Cl+12.92ClEITakhistov and Ponomarev, 1994Unpublished result of N.S.Khlebnikova, V.M.Orlov, D.A.Ponomarev, and V.V.Takhistov; LL

De-protonation reactions

C6H3Cl2- + Hydrogen cation = Benzene, 1,2-dichloro-

By formula: C6H3Cl2- + H+ = C6H4Cl2

Quantity Value Units Method Reference Comment
Deltar1578. ± 8.8kJ/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.; B
Quantity Value Units Method Reference Comment
Deltar1543. ± 8.4kJ/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: o-dichlorobenzene. Anion assigned based on ab initio calculations.; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director


Mass spectrum (electron ionization)

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

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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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 Japan AIST/NIMC Database- Spectrum MS-NW- 987
NIST MS number 227765

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References

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

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]

Sinke and Stull, 1958
Sinke, G.C.; Stull, D.R., Heats of combustion of some organic compounds containing chlorine, J. Phys. Chem., 1958, 62, 397-401. [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]

Bjellerup and Smith, 1954
Bjellerup, L.; Smith, L., Heats of combustion of some organic chloro-compounds, Kgl. Fysiograph. Sallskap. Lund Forh., 1954, 24, 1-13. [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]

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]

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]

Kailuru and Abburi, 1988
Kailuru, R.; Abburi, K., Isobaric Vapor-Liquid Equilibria of Methyl Ethyl Ketone(1) + o-Dichlorobenzene(2), + Bromobenzene(2), and + Nitrobenzene(2), J. Chem. Eng. Data, 1988, 33, 251. [all data]

Walling and Miller, 1957
Walling, C.; Miller, B., The Relative Reactivities of Substituted Toluenes toward Chlorine Atoms, J. Am. Chem. Soc., 1957, 79, 4181. [all data]

Dreisbach and Martin, 1949
Dreisbach, R.R.; Martin, R.A., Physical Data on Some Organic Compounds, Ind. Eng. Chem., 1949, 41, 2875-8. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [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]

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]

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]

Aldrich Chemical Company Inc., 1990
Aldrich Chemical Company Inc., Catalog Handbook of Fine Chemicals, Aldrich Chemical Company, Inc., Milwaukee WI, 1990, 1. [all data]

Grayson and Fosbraey, 2006
Grayson, B. Terence; Fosbraey, Lynda A., Determination of the vapour pressure of pesticides, Pestic. Sci., 2006, 13, 3, 269-278, https://doi.org/10.1002/ps.2780130308 . [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]

Polednicek, Guetachew, et al., 1996
Polednicek, M.; Guetachew, T.; Jose, J.; Ruzicka, V.; Rohac, V.; Zabransky, M., Vapor pressures and sublimation pressures of dichlorobenzenes (1,2-,1,3-, and 1,4-), trichlorobenzenes (1,2,3- and 1,3,5-), and pentachlorobenzene, ELDATA: Int. Electron. J. Phys. Chem. Data, 1996, 2, 2, 41. [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]

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]

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]

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]

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]

Godnev and Sverdlin, 1961
Godnev, I.N.; Sverdlin, A.S., Equilibrium and dichlorobenzene isomer (Corrections), Russ. J. Phys. Chem. (Engl. Transl.), 1961, 35, 231-232. [all data]

Steelhammer and Wentworth, 1969
Steelhammer, J.C.; Wentworth, W.E., Correlation of Electron Beam and Thermal Electron Attachment Studies for Some Chloro, Bromo, Iodo Aromatic Compounds, J. Chem. Phys., 1969, 51, 5, 1802, https://doi.org/10.1063/1.1672262 . [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]

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]

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]

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]

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

Takhistov and Ponomarev, 1994
Takhistov, V.V.; Ponomarev, D.A., Isodesmic reactions and thermochemistry of ions, Org. Mass Spectrom., 1994, 29, 395. [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References