Benzene, 1,3,5-trichloro-
- Formula: C6H3Cl3
- Molecular weight: 181.447
- IUPAC Standard InChIKey: XKEFYDZQGKAQCN-UHFFFAOYSA-N
- 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
- Permanent link for this species. Use this link for bookmarking this species for future reference.
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Gas phase thermochemistry data
Go To: Top, Gas phase ion energetics data, Gas Chromatography, 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 |
---|---|---|---|---|---|
ΔfH°gas | -2.6 ± 1.4 | kJ/mol | Ccr | Yan, Gu, et al., 1987 | |
ΔfH°gas | -13.36 | kJ/mol | Ccr | Platonov and Simulin, 1985 |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Gas Chromatography, 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 ± 0.06 | eV | N/A | N/A | L |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.33998 | ECD | Chen and Wentworth, 1981 | G3MP2B3 calculations indicate an EA of ca. -0.03 eV, and HOF(A-) = -3 kcal/mol; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.2 | PE | Maier and Thommen, 1982 | LBLHLM |
9.32 ± 0.03 | PE | Ruscic, Klasinc, et al., 1981 | LLK |
9.30 | PE | Kimura, Katsumata, et al., 1981 | LLK |
9.34 ± 0.02 | PE | Maier and Marthaler, 1978 | LLK |
9.5 ± 0.15 | CTS | Voigt and Reid, 1964 | RDSH |
9.36 | PE | Streets and Ceasar, 1973 | Vertical value; LLK |
De-protonation reactions
C6H2Cl3- + =
By formula: C6H2Cl3- + H+ = C6H3Cl3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1545. ± 8.8 | kJ/mol | G+TS | Schlosser, Marzi, et al., 2001 | gas phase; Acid: 1,3,5-trichlorobenzene.; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1510. ± 8.4 | kJ/mol | IMRE | Schlosser, Marzi, et al., 2001 | gas phase; Acid: 1,3,5-trichlorobenzene.; B |
Gas Chromatography
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, 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
Kovats' RI, non-polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | SE-30 | 160. | 1150.0 | Santiuste, Harangi, et al., 2003 | |
Capillary | HP-5 | 120. | 1162.5 | Santiuste, Harangi, et al., 2003 | |
Capillary | HP-5 | 120. | 1153.7 | Santiuste J.M. and Takacs J.M., 2003 | 60. m/0.25 mm/0.25 μm, N2 |
Capillary | HP-5 | 140. | 1165.1 | Santiuste J.M. and Takacs J.M., 2003 | 60. m/0.25 mm/0.25 μm, N2 |
Capillary | DB-5 | 110. | 1146.29 | Gerbino, Garbarino, et al., 1996 | 30. m/0.53 mm/1.5 μm, N2 |
Capillary | DB-5 | 70. | 1122.94 | Gerbino, Garbarino, et al., 1996 | 30. m/0.53 mm/1.5 μm, N2 |
Capillary | DB-5 | 90. | 1133.72 | Gerbino, Garbarino, et al., 1996 | 30. m/0.53 mm/1.5 μm, N2 |
Capillary | SE-30 | 0. | 1091. | Spieksma, Luijk, et al., 1994 | |
Capillary | SE-30 | 160. | 1131. | Evans and Haken, 1989 | Column length: 25. m; Column diameter: 0.32 mm |
Capillary | SE-30 | 160. | 1150. | Tarjan, Nyiredy, et al., 1989 | |
Capillary | SE-30 | 120. | 1131. | Haken and Korhonene, 1983 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | SE-30 | 140. | 1144. | Haken and Korhonene, 1983 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Capillary | SE-30 | 160. | 1150. | Haken and Korhonene, 1983 | N2; Column length: 25. m; Column diameter: 0.22 mm |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | ZB-Wax | 120. | 1550.0 | Pérez-Parajón, Santiuste, et al., 2004 | 60. m/0.25 mm/0.25 μm |
Capillary | ZB-Wax | 140. | 1569.3 | Pérez-Parajón, Santiuste, et al., 2004 | 60. m/0.25 mm/0.25 μm |
Capillary | ZB-Wax | 160. | 1589.5 | Pérez-Parajón, Santiuste, et al., 2004 | 60. m/0.25 mm/0.25 μm |
Capillary | Carbowax 20M | 160. | 1515. | Evans and Haken, 1989 | Column length: 22. m; Column diameter: 0.3 mm |
Capillary | Carbowax 20M | 140. | 1515. | Haken and Korhonene, 1983 | N2; Column length: 22. m; Column diameter: 0.3 mm |
Capillary | Carbowax 20M | 160. | 1545. | Haken and Korhonene, 1983 | N2; Column length: 22. m; Column diameter: 0.3 mm |
Capillary | Carbowax 20M | 180. | 1590. | Haken and Korhonene, 1983 | N2; Column length: 22. m; Column diameter: 0.3 mm |
Van Den Dool and Kratz RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-5 | 1117.64 | Gerbino, Garbarino, et al., 1996 | 30. m/0.53 mm/1.5 μm, N2, 2. K/min; Tstart: 50. C |
Capillary | DB-5 | 1122.48 | Gerbino, Garbarino, et al., 1996 | 30. m/0.53 mm/1.5 μm, N2, 2. K/min; Tstart: 50. C |
Capillary | DB-5 | 1127.13 | Gerbino, Garbarino, et al., 1996 | 30. m/0.53 mm/1.5 μm, N2, 2. K/min; Tstart: 50. C |
Capillary | DB-1 | 1128. | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.25 μm, N2, 100. C @ 0. min, 10. K/min |
Capillary | DB-1 | 1123. | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.25 μm, N2, 100. C @ 0. min, 5. K/min |
Capillary | DB-1 | 1115. | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.25 μm, N2, 50. C @ 0. min, 10. K/min |
Capillary | DB-1 | 1109. | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.25 μm, N2, 50. C @ 0. min, 5. K/min |
Capillary | Petrocol DH | 1112. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Van Den Dool and Kratz RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Packed | SE-30 | 1146. | Peng, Ding, et al., 1988 | Supelcoport; Chromosorb; Column length: 3.05 m; Program: 40C(5min) => 10C/min => 200C or 250C (60min) |
Van Den Dool and Kratz RI, polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-Wax | 1517.29 | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.5 μm, N2, 10. K/min; Tstart: 100. C |
Capillary | DB-Wax | 1517.48 | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.5 μm, N2, 5. K/min; Tstart: 100. C |
Capillary | DB-Wax | 1529.51 | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.5 μm, N2, 10. K/min; Tstart: 50. C |
Capillary | DB-Wax | 1517.60 | Gerbino and Castello, 1995 | 30. m/0.235 mm/0.5 μm, N2, 5. K/min; Tstart: 50. C |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 1084. | Messadi and Ali-Mokhnache, 1993 | 2. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 80. C |
Capillary | OV-101 | 1095. | Messadi and Ali-Mokhnache, 1993 | 2. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 80. C |
Capillary | OV-101 | 1096. | Messadi and Ali-Mokhnache, 1993 | 2. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 80. C |
Capillary | OV-101 | 1100. | Messadi and Ali-Mokhnache, 1993 | 2. K/min; Column length: 25. m; Column diameter: 0.20 mm; Tstart: 80. C |
Capillary | Ultra-1 | 1112. | Okumura, 1991 | 25. m/0.32 mm/0.25 μm, He, 3. K/min; Tstart: 80. C; Tend: 260. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Methyl Silicone | 1131. | Yu and Zazhi, 2005 | Program: not specified |
Capillary | CP Sil 2 | 1151. | Fuhrer, Deissler, et al., 1997 | 55. m/0.25 mm/0.25 μm, N2; Program: 40C(3min) => 20C/min => 80C => 2C/min => 240C(45min) |
Capillary | SPB-1 | 1106. | Vezzani, Moretti, et al., 1994 | Column length: 30. m; Column diameter: 0.32 mm; Program: not specified |
Capillary | PTE-5 | 1145. | Nakano, Fujimori, et al., 1992 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min) |
Capillary | Ultra-2 | 1158. | Nakano, Fujimori, et al., 1992 | 25. m/0.20 mm/0.33 μm; Program: 50 0C (2 min) 30 0C/min -> 200 0C 8 0C/min -> 280 0C (10 min) |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 1113. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Lee's RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | HP5-MS | 190. | Vrana, Paschke, et al., 2005 | 30. m/0.25 mm/0.25 μm, Helium, 50. C @ 5. min, 5. K/min, 280. C @ 10. min |
References
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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]
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]
Santiuste, Harangi, et al., 2003
Santiuste, J.M.; Harangi, J.; Takács, J.M.,
Mosaic increments for predicting the gas chromatographic retention data of the chlorobenzenes,
J. Chromatogr. A, 2003, 1002, 1-2, 155-168, https://doi.org/10.1016/S0021-9673(03)00736-2
. [all data]
Santiuste J.M. and Takacs J.M., 2003
Santiuste J.M.; Takacs J.M.,
Relationships between retention data of benzene and chlorobenzenes with their physico-chemical properties and topological indices,
Chromatographia, 2003, 58, 87-96. [all data]
Gerbino, Garbarino, et al., 1996
Gerbino, T.C.; Garbarino, G.; Petit-Bon, P.,
Programmed temperature retention indices: calculation of linear programmed temperature retention indices of halogenated benzenes from isothermal data,
Ann. Chim. (Rome), 1996, 86, 63-75. [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
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Evans and Haken, 1989
Evans, M.B.; Haken, J.K.,
Dispersion and selectivity indices in gas chromatography. IV. Chlorinated aromatic compounds,
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. [all data]
Tarjan, Nyiredy, et al., 1989
Tarjan, G.; Nyiredy, Sz.; Gyor, M.; Lombosi, E.R.; Lombosi, T.S.; Budahegyi, M.V.; Meszaros, S.Y.; Takacs, J.M.,
Review. Thirtieth Anniversary of the Retention Index According to Kovats in Gas-Liquid Chromatography,
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Haken and Korhonene, 1983
Haken, J.K.; Korhonene, I.O.O.,
Retention increments of isomeric chlorobenzenes,
J. Chromatogr., 1983, 265, 323-327, https://doi.org/10.1016/S0021-9673(01)96727-5
. [all data]
Pérez-Parajón, Santiuste, et al., 2004
Pérez-Parajón, J.M.; Santiuste, J.M.; Takács, J.M.,
Sensitivity of the methylbenzenes and chlorobenzenes retention index to column temperature, stationary phase polarity, and number and chemical nature of substituents,
J. Chromatogr. A, 2004, 1048, 2, 223-232, https://doi.org/10.1016/j.chroma.2004.07.028
. [all data]
Gerbino and Castello, 1995
Gerbino, T.C.; Castello, G.,
Prediction of programmed temperature retention indices on capillary columns of different polarities,
J. Chromatogr. A, 1995, 699, 1-2, 161-171, https://doi.org/10.1016/0021-9673(95)00024-H
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White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211
. [all data]
Peng, Ding, et al., 1988
Peng, C.T.; Ding, S.F.; Hua, R.L.; Yang, Z.C.,
Prediction of Retention Indexes I. Structure-Retention Index Relationship on Apolar Columns,
J. Chromatogr., 1988, 436, 137-172, https://doi.org/10.1016/S0021-9673(00)94575-8
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Messadi and Ali-Mokhnache, 1993
Messadi, D.; Ali-Mokhnache, S.,
Calculation of retention indices and peak widths in temperature programmed gas-liquid chromatography,
Chromatographia, 1993, 37, 5/6, 264-270, https://doi.org/10.1007/BF02278631
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Okumura, 1991
Okumura, T.,
retention indices of environmental chemicals on methyl silicone capillary column,
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Yu and Zazhi, 2005
Yu, H.; Zazhi, J.,
Relationship between chromatogram retention index and toxicity of chlorinated phenols and chlorinated benzenes to Guppy,
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Fuhrer, Deissler, et al., 1997
Fuhrer, U.; Deissler, A.; Schreitmuller, J.; Ballschmiter, K.,
Analysis of Halogenated Methoxybenzenes and Hexachlorobenzene (HCB) in the Picogram m-3 Range in Marine Air,
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Vezzani, Moretti, et al., 1994
Vezzani, S.; Moretti, P.; Castello, G.,
Fast and Accurate Method for the Automatic Prediction of Programmed-Temperature Retention Times,
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Nakano, Fujimori, et al., 1992
Nakano, T.; Fujimori, K.; Takaishi, Y.; Okuno, T.,
GC/MS-SIM analysis of polychlorobenzenes, polychlorophenols and polychloronaphthalenes,
Report of the Environmental Science Institute of Hyogo Prefecture, 1992, 24, 30-37. [all data]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Vrana, Paschke, et al., 2005
Vrana, B.; Paschke, H.; Paschke, A.; Popp, P.; Schuurmann, G.,
Performance of semipermeable membrane devices for sampling of organic contaminants in groun water,
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Notes
Go To: Top, Gas phase thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
EA Electron affinity IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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