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Benzene, 1,3,5-trichloro-

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Gas phase thermochemistry data

Go To: Top, 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, Notes

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
Deltafgas-0.61 ± 0.34kcal/molCcrYan, Gu, et al., 1987 
Deltafgas-3.193kcal/molCcrPlatonov and Simulin, 1985 

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
Deltafsolid-17.99 ± 0.32kcal/molCcrYan, Gu, et al., 1987 
Quantity Value Units Method Reference Comment
Deltacsolid-665.73 ± 0.31kcal/molCcrYan, Gu, et al., 1987 
Deltacsolid-664.90 ± 0.12kcal/molCcrPlatonov and Simulin, 1985 

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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil481.2KN/AAldrich Chemical Company Inc., 1990BS
Quantity Value Units Method Reference Comment
Tfus334.45KN/ADonnelly, Drewes, et al., 1990Uncertainty assigned by TRC = 0.2 K; TRC
Tfus336.3KN/AMiller, Ghodbane, et al., 1984Uncertainty assigned by TRC = 0.2 K; TRC
Tfus336.7KN/APlato and Glasgow, 1969Uncertainty assigned by TRC = 0.1 K; TRC
Tfus336.2KN/ADiepen and Scheffer, 1948Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Deltavap14.kcal/molGCSpieksma, Luijk, et al., 1994Based on data from 413. - 453. K.; AC
Quantity Value Units Method Reference Comment
Deltasub17.4 ± 0.1kcal/molCYan, Gu, et al., 1987ALS
Deltasub12.91kcal/molEPlatonov and Simulin, 1985ALS
Deltasub17.4 ± 0.1kcal/molN/AYan, Gu, et al., 1985See also Yan, Gu, et al., 1987, 2.; AC

Enthalpy of vaporization

DeltavapH (kcal/mol) Temperature (K) Method Reference Comment
12.0 ± 0.02375.DMBlok, van Genderen, et al., 2001Based on data from 338. - 415. K.; AC
12.4337.N/ARohác, Ruzicka, et al., 1999AC
11.7351.AStephenson and Malanowski, 1987Based on data from 336. - 482. K. See also Stull, 1947.; AC

Antoine Equation Parameters

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

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Temperature (K) A B C Reference Comment
336.9 - 481.64.601382067.313-32.267Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of sublimation

DeltasubH (kcal/mol) Temperature (K) Method Reference Comment
13.5291.RGSears and Hopke, 1949Based on data from 282. - 301. K. See also Jones, 1960.; AC

Enthalpy of fusion

DeltafusH (kcal/mol) Temperature (K) Reference Comment
4.197335.9van der Linde, van Miltenburg, et al., 2005AC
4.35336.7Acree, 1991AC

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 by: John E. Bartmess

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

C6H2Cl3- + Hydrogen cation = Benzene, 1,3,5-trichloro-

By formula: C6H2Cl3- + H+ = C6H3Cl3

Quantity Value Units Method Reference Comment
Deltar369.2 ± 2.1kcal/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: 1,3,5-trichlorobenzene.
Quantity Value Units Method Reference Comment
Deltar360.8 ± 2.0kcal/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: 1,3,5-trichlorobenzene.

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
0.63 LN/A

Gas phase ion energetics data

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

Quantity Value Units Method Reference Comment
IE (evaluated)9.30 ± 0.06eVN/AN/AL

Electron affinity determinations

EA (eV) Method Reference Comment
0.33998ECDChen and Wentworth, 1981G3MP2B3 calculations indicate an EA of ca. -0.03 eV, and HOF(A-) = -3 kcal/mol; B

Ionization energy determinations

IE (eV) Method Reference Comment
9.2PEMaier and Thommen, 1982LBLHLM
9.32 ± 0.03PERuscic, Klasinc, et al., 1981LLK
9.30PEKimura, Katsumata, et al., 1981LLK
9.34 ± 0.02PEMaier and Marthaler, 1978LLK
9.5 ± 0.15CTSVoigt and Reid, 1964RDSH
9.36PEStreets and Ceasar, 1973Vertical value; LLK

De-protonation reactions

C6H2Cl3- + Hydrogen cation = Benzene, 1,3,5-trichloro-

By formula: C6H2Cl3- + H+ = C6H3Cl3

Quantity Value Units Method Reference Comment
Deltar369.2 ± 2.1kcal/molG+TSSchlosser, Marzi, et al., 2001gas phase; Acid: 1,3,5-trichlorobenzene.; B
Quantity Value Units Method Reference Comment
Deltar360.8 ± 2.0kcal/molIMRESchlosser, Marzi, et al., 2001gas phase; Acid: 1,3,5-trichlorobenzene.; B

IR Spectrum

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, Mass spectrum (electron ionization), References, Notes

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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Mass 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 Chuck Anderson, Aldrich Chemical Co.
NIST MS number 107765

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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.

Yan, Gu, et al., 1987
Yan, H.; Gu, J.; An, X.; Hu, R., Standard enthalpies of formation and enthlpies of isomerization of trichlorobenzenes, Huaxue Xuebao, 1987, 45, 1184-1187. [all data]

Platonov and Simulin, 1985
Platonov, V.A.; Simulin, Yu.N., Determination of the standard enthalpies of formation of polychlorobenzenes. III. The standard enthalpies of formation of mono-1,2,4- and 1,3,5-tri-, and 1,2,3,4- and 1,2,3,5-tetrachlorobenzenes, Russ. J. Phys. Chem. (Engl. Transl.), 1985, 59, 179-181. [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]

Donnelly, Drewes, et al., 1990
Donnelly, J.R.; Drewes, L.A.; Johnson, R.L.; Munslow, W.D.; Knapp, K.K.; Sovocool, G.W., Purity and heat of fusion data for environmental standards as determined by differential scanning calorimetry, Thermochim. Acta, 1990, 167, 2, 155, https://doi.org/10.1016/0040-6031(90)80476-F . [all data]

Miller, Ghodbane, et al., 1984
Miller, M.M.; Ghodbane, S.; Wasik, S.P.; Tewari, Y.B.; Martire, D.E., Aqueous Solubilities, Octanol/Water Partition Coefficients, and Entropies of Melting of Chlorinated Benzenes and Biphenyls, J. Chem. Eng. Data, 1984, 29, 184-190. [all data]

Plato and Glasgow, 1969
Plato, C.; Glasgow, A.R., Jr., Differential scanning calorimetry as a general method for determining the purity and heat of fusion of high-purity organic chemicals. Application to 95 compounds, Anal. Chem., 1969, 41, 2, 330, https://doi.org/10.1021/ac60271a041 . [all data]

Diepen and Scheffer, 1948
Diepen, G.A.M.; Scheffer, F.E.C., On Critical Phenomena of Saturated Solutions in Binary Systems, J. Am. Chem. Soc., 1948, 70, 4081. [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]

Yan, Gu, et al., 1985
Yan, Haike; Gu, Jiangou; Hu, Rihen, Sublimation Calorimeter and the Measurement of Enthalpies of Vaporization and Sublimation of Trichlorobenzenes, Acta Phys. Chim. Sin., 1985, 1, 6, 543-546, https://doi.org/10.3866/PKU.WHXB19850607 . [all data]

Yan, Gu, et al., 1987, 2
Yan, H.; Gu, J.; An, X.; Hu, R.-H., Huaxue Xuebao, 1987, 45, 1184. [all data]

Blok, van Genderen, et al., 2001
Blok, Jacobus G.; van Genderen, Aad C.G.; van der Linde, Peter R.; Oonk, Harry A.J., Vapour pressures of crystalline 1,2,4,5-tetrachlorobenzene, and crystalline and liquid 1,3,5-trichlorobenzene and 1,2,4,5-tetramethylbenzene, The Journal of Chemical Thermodynamics, 2001, 33, 9, 1097-1106, https://doi.org/10.1006/jcht.2000.0819 . [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]

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]

Stull, 1947
Stull, Daniel R., Vapor Pressure of Pure Substances. Organic and Inorganic Compounds, Ind. Eng. Chem., 1947, 39, 4, 517-540, https://doi.org/10.1021/ie50448a022 . [all data]

Sears and Hopke, 1949
Sears, G.W.; Hopke, E.R., Vapor Pressures of the Isomeric Trichlorobenzenes in the Low Pressure Region, J. Am. Chem. Soc., 1949, 71, 7, 2575-2576, https://doi.org/10.1021/ja01175a094 . [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]

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]

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]

Chen and Wentworth, 1981
Chen, E.C.M.; Wentworth, W.E., Correlation and Prediction of Electron Capture Response from Molecular Parameters, J. Chromatogr., 1981, 217, 151, https://doi.org/10.1016/S0021-9673(00)88069-3 . [all data]

Maier and Thommen, 1982
Maier, J.P.; Thommen, F., Photoelectron-photoion coincidence studies of halobenzene cations in their excited electronic states, J. Chem. Phys., 1982, 77, 4427. [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. 2. Trichlorobenzenes, tetrachlorobenzenes, and pentachlorobenzene, J. Phys. Chem., 1981, 85, 1490. [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]

Voigt and Reid, 1964
Voigt, E.M.; Reid, C., Ionization potentials of substituted benzenes and their charge-transfer spectra with tetracyanoethylene, J. Am. Chem. Soc., 1964, 86, 3930. [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]


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