Benzene, 1,3,5-trichloro-

• Formula: C₆H₃Cl₃
• Molecular weight: 181.447
• IUPAC Standard InChI: InChI=1S/C6H3Cl3/c7-4-1-5(8)3-6(9)2-4/h1-3H Copy

  
• IUPAC Standard InChIKey: XKEFYDZQGKAQCN-UHFFFAOYSA-N Copy
• CAS Registry Number: 108-70-3
• 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: s-Trichlorobenzene; 1,3,5-Trichlorobenzene; sym-Trichlorobenzene; UN 2321
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• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Mass spectrum (electron ionization)
  • References
  • Notes
• Other data available:
  • Reaction thermochemistry data
  • IR Spectrum
  • Gas Chromatography
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• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

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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

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

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

Enthalpy of vaporization

Antoine Equation Parameters

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

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Enthalpy of sublimation

Enthalpy of fusion

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)

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

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
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

Electron affinity determinations

Ionization energy determinations

De-protonation reactions

C₆H₂Cl₃^- +  =

By formula: C₆H₂Cl₃^- + H⁺ = C₆H₃Cl₃

Mass spectrum (electron ionization)

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

Spectrum

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Additional Data

References

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

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 π orbitals of halobenzenes, Mol. Phys., 1973, 26, 1037. [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, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), References

• Symbols used in this document:
  

  EA	Electron affinity
  IE (evaluated)	Recommended ionization energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  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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