Trichloromethane
- Formula: CHCl3
- Molecular weight: 119.378
- IUPAC Standard InChIKey: HEDRZPFGACZZDS-UHFFFAOYSA-N
- CAS Registry Number: 67-66-3
- 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. - Isotopologues:
- Other names: Chloroform; Freon 20; Methane, trichloro-; R 20; Trichloroform; CHCl3; Formyl trichloride; Methane trichloride; Methenyl trichloride; Methyl trichloride; Chloroforme; Cloroformio; NCI-C02686; R 20 (refrigerant); Trichloormethaan; Trichlormethan; Triclorometano; Rcra waste number U044; UN 1888; NSC 77361; F 20
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Gas phase thermochemistry data
Go To: Top, Condensed 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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -24.661 | kcal/mol | Review | Chase, 1998 | Data last reviewed in December, 1968 |
ΔfH°gas | -24.59 ± 0.60 | kcal/mol | Review | Manion, 2002 | derived from recommended ΔfHliquid° and ΔvapH°; DRB |
Quantity | Value | Units | Method | Reference | Comment |
S°gas,1 bar | 70.652 | cal/mol*K | Review | Chase, 1998 | Data last reviewed in December, 1968 |
Gas Phase Heat Capacity (Shomate Equation)
Cp° = A + B*t + C*t2 + D*t3 +
E/t2
H° − H°298.15= A*t + B*t2/2 +
C*t3/3 + D*t4/4 − E/t + F − H
S° = A*ln(t) + B*t + C*t2/2 + D*t3/3 −
E/(2*t2) + G
Cp = heat capacity (cal/mol*K)
H° = standard enthalpy (kcal/mol)
S° = standard entropy (cal/mol*K)
t = temperature (K) / 1000.
View plot Requires a JavaScript / HTML 5 canvas capable browser.
Temperature (K) | 298. to 1200. | 1200. to 6000. |
---|---|---|
A | 10.57530 | 24.25339 |
B | 27.40760 | 0.819731 |
C | -21.22810 | -0.157110 |
D | 6.190230 | 0.010446 |
E | -0.124954 | -2.234230 |
F | -29.27560 | -37.23709 |
G | 75.46489 | 92.53241 |
H | -24.65990 | -24.65990 |
Reference | Chase, 1998 | Chase, 1998 |
Comment | Data last reviewed in December, 1968 | Data last reviewed in December, 1968 |
Condensed phase thermochemistry data
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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
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 |
---|---|---|---|---|---|
ΔfH°liquid | -32.05 ± 0.60 | kcal/mol | Review | Manion, 2002 | adopted combustion calorimetry data of Hu and Sinke, 1969 with increased uncertainty to reflect other data; DRB |
ΔfH°liquid | -32.10 | kcal/mol | Ccr | Hu and Sinke, 1969, 2 | ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -113.10 | kcal/mol | Ccr | Hu and Sinke, 1969, 2 | ALS |
ΔcH°liquid | -113.3 ± 2.0 | kcal/mol | Ccb | Smith, Bjellerup, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -113. ± 2. kcal/mol; ALS |
Constant pressure heat capacity of liquid
Cp,liquid (cal/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
27.306 | 298.15 | Grolier, Roux-Desgranges, et al., 1993 | DH |
27.06 | 298.15 | Shehatta, 1993 | DH |
27.323 | 298.15 | Barta, Kooner, et al., 1989 | DH |
27.330 | 298.15 | Barta, Kooner, et al., 1989, 2 | DH |
27.61 | 298.15 | Petrov, Peshekhodov, et al., 1989 | T = 258.15, 278.15, 298.15, 318.15 K.; DH |
27.211 | 298.15 | Grolier, Roux-Desgranges, et al., 1987 | DH |
27.61 | 298.15 | Al'per, Peshekhodov, et al., 1986 | DH |
27.182 | 298.15 | Hepler, Kooner, et al., 1985 | DH |
27.309 | 298.15 | Inglese, Castagnolo, et al., 1981 | DH |
27.77 | 293. | Rastorguev and Ganiev, 1967 | T = 293 to 333 K.; DH |
27.10 | 300. | Harrison and Moelwyn-Hughes, 1957 | T = 243 to 303 K.; DH |
27.25 | 303.2 | Harrison and Moelwyn-Hughes, 1957 | T = 245 to 303 K. Unsmoothed experimental datum.; DH |
27.290 | 298. | Staveley, Tupman, et al., 1955 | T = 284 to 329 K.; DH |
27.99 | 298. | Kurbatov, 1948 | T = -52 to 51°C. Mean Cp, four temperatures.; DH |
33.39 | 303.6 | Phillip, 1939 | DH |
27.01 | 298.1 | Richards and Wallace, 1932 | T = 293 to 323 K.; DH |
27.61 | 293.2 | Williams and Daniels, 1925 | T = 20 to 50°C.; DH |
27.89 | 303. | Willams and Daniels, 1924 | T = 295 to 315 K. Equation only.; DH |
Gas phase ion energetics data
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, 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
LL - Sharon G. Lias and Joel F. Liebman
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 11.37 ± 0.02 | eV | N/A | N/A | L |
Electron affinity determinations
EA (eV) | Method | Reference | Comment |
---|---|---|---|
0.62 ± 0.16 | IMRB | Staneke, Groothuis, et al., 1995 | EA > EA(CH2S-.), and Cl-A(CHCl2.) < Cl-A(CHCl3). May be ion-molecule complex.; B |
1.756 ± 0.052 | SI | Gaines, Kay, et al., 1966 | The Magnetron method, lacking mass analysis, is not considered reliable.; B |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
11.41 ± 0.02 | PI | Wang and Leroi, 1983 | LBLHLM |
11.3 | PE | Von Niessen, Asbrink, et al., 1982 | LBLHLM |
11.48 | PE | Kimura, Katsumata, et al., 1981 | LLK |
11.37 ± 0.02 | PI | Werner, Tsai, et al., 1974 | LLK |
11.40 | PE | Dewar and Worley, 1969 | RDSH |
11.50 | CI | Cermak, 1968 | RDSH |
11.42 ± 0.03 | PI | Watanabe, 1957 | RDSH |
11.5 | PE | Von Niessen, Asbrink, et al., 1982 | Vertical value; LBLHLM |
11.48 | PE | Dixon, Murrell, et al., 1971 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C+ | 24.62 | ? | EI | Reed and Snedden, 1956 | RDSH |
CCl+ | 16.3 ± 0.2 | ? | EI | Hobrock and Kiser, 1964 | RDSH |
CCl2+ | 12.2 | ? | EI | Shapiro and Lossing, 1968 | RDSH |
CCl3+ | 11.70 ± 0.09 | H | EI | Martin, Lampe, et al., 1966 | RDSH |
CH+ | 16.8 ± 1.0 | Cl2+Cl | EI | Ogawa, Miyoshi, et al., 1982 | LBLHLM |
CH+ | 23.9 ± 0.3 | ? | EI | Hobrock and Kiser, 1964 | RDSH |
CHCl+ | 17.5 ± 0.2 | ? | EI | Hobrock and Kiser, 1964 | RDSH |
CHCl2+ | 11.52 | Cl | EI | Holmes, Lossing, et al., 1988 | LL |
CHCl2+ | 11.49 ± 0.02 | Cl | PI | Werner, Tsai, et al., 1974 | LLK |
CHCl2+ | 11.52 | Cl | EI | Lossing, 1972 | LLK |
CHCl2+ | 11.64 ± 0.20 | Cl | EI | Hobrock and Kiser, 1964 | RDSH |
CHCl2+ | 11.7 ± 0.1 | Cl | EI | Harrison and Shannon, 1962 | RDSH |
CHCl2+ | 12.43 ± 0.02 | Cl | EI | Reed and Snedden, 1956 | RDSH |
Cl+ | 22.0 ± 0.3 | ? | EI | Hobrock and Kiser, 1964 | RDSH |
H+ | 20.5 ± 1.7 | 4H+CCl3 | EI | Ogawa, Miyoshi, et al., 1982 | LBLHLM |
De-protonation reactions
CCl3- + =
By formula: CCl3- + H+ = CHCl3
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 360.33 | kcal/mol | Acid | Paulino and Squires, 1991 | gas phase; B |
ΔrH° | 357.6 ± 2.1 | kcal/mol | G+TS | Paulino and Squires, 1991 | gas phase; B |
ΔrH° | 357.0 ± 6.1 | kcal/mol | G+TS | Bohme, Lee-Ruff, et al., 1972 | gas phase; > acetone, <= C5H6; value altered from reference due to change in acidity scale; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 349.9 ± 2.0 | kcal/mol | IMRB | Paulino and Squires, 1991 | gas phase; B |
ΔrG° | 349.9 ± 3.0 | kcal/mol | IMRB | Born, Ingemann, et al., 2000 | gas phase; B |
ΔrG° | 349.3 ± 6.0 | kcal/mol | IMRB | Bohme, Lee-Ruff, et al., 1972 | gas phase; > acetone, <= C5H6; value altered from reference due to change in acidity scale; B |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry 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.
Chase, 1998
Chase, M.W., Jr.,
NIST-JANAF Themochemical Tables, Fourth Edition,
J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1-1951. [all data]
Manion, 2002
Manion, J.A.,
Evaluated Enthalpies of Formation of the Stable Closed Shell C1 and C2 Chlorinated Hydrocarbons,
J. Phys. Chem. Ref. Data, 2002, 31, 1, 123-172, https://doi.org/10.1063/1.1420703
. [all data]
Hu and Sinke, 1969
Hu, A.T.; Sinke, G.C.,
Combustion calorimetry of some chlorinated organic compounds,
J. Chem. Thermodyn., 1969, 1, 6, 507, https://doi.org/10.1016/0021-9614(69)90010-X
. [all data]
Hu and Sinke, 1969, 2
Hu, A.T.; Sinke, G.C.,
Combustion calorimetry of some chlorinated organic compounds,
J. Chem. Thermodyn., 1969, 1, 507-513. [all data]
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]
Grolier, Roux-Desgranges, et al., 1993
Grolier, J.-P.E.; Roux-Desgranges, G.; Berkane, M.; Jimenez, E.; Wilhelm, E.,
Heat capacities and densities of mixtures of very polar substances 2. Mixtures containing N,N-dimethylformamide,
J. Chem. Thermodynam., 1993, 25(1), 41-50. [all data]
Shehatta, 1993
Shehatta, I.,
Heat capacity at constant pressure of some halogen compounds,
Thermochim. Acta, 1993, 213, 1-10. [all data]
Barta, Kooner, et al., 1989
Barta, L.; Kooner, Z.S.; Hepler, L.G.; Roux-Desgranges, G.; Grolier, J.-P.E.,
Thermodynamics of complex formation in chloroform and 1,4-dioxane,
Can. J. Chem., 1989, 67, 1225-1229. [all data]
Barta, Kooner, et al., 1989, 2
Barta, L.; Kooner, Z.S.; Hepler, L.G.; Roux-Desgranges, G.; Grolier, J.-P.E.,
Thermal and volumetric properties of chloroform dimethylsulfoxide: Thermodynamic analysis using the ideal associated solution model,
J. Solution Chem., 1989, 18(7), 663-673. [all data]
Petrov, Peshekhodov, et al., 1989
Petrov, A.N.; Peshekhodov, P.B.; Al'per, G.A.,
Heat capacity of non-aqueous solutions of non-electrolyts with N,N-dimethylformamide as a base, Sbornik Nauch. Trud., Termodin. Rast. neelect., Ivanovo,
Inst. nevod. rast., 1989, Akad. [all data]
Grolier, Roux-Desgranges, et al., 1987
Grolier, J.-P.E.; Roux-Desgranges, G.; Kooner, Z.S.; Smith, J.F.; Hepler, L.G.,
Thermal and volumetric properties of chloroform + benzene mixtures and the ideal associated solution model of complex formation,
J. Solution Chem., 1987, 16, 745-752. [all data]
Al'per, Peshekhodov, et al., 1986
Al'per, G.A.; Peshekhodov, P.B.; Nikiforov, M.Yu.; Petrov, A.N.; Krestov, G.A.,
Specific heats and features of the intermolecular interactions in the system chloroform-acetone,
Zhur. Obshchei Khim., 1986, 56(8), 1688-1691. [all data]
Hepler, Kooner, et al., 1985
Hepler, L.G.; Kooner, Z.S.; Roux-Desgranges, G.; Grolier, J.-P.E.,
Thermal and volumetric properties of chloroform + triethylamine mixtures and the ideal associated solution model of complex formation,
J. Solution Chem., 1985, 14(8), 579-594. [all data]
Inglese, Castagnolo, et al., 1981
Inglese, A.; Castagnolo, M.; Dell'Atti, A.; DeGiglio, A.,
Thermochim. Acta, 1981, 77-87. [all data]
Rastorguev and Ganiev, 1967
Rastorguev, Yu.L.; Ganiev, Yu.A.,
Study of the heat capacity of selected solvents,
Izv. Vyssh. Uchebn. Zaved. Neft Gaz. 10, 1967, No.1, 79-82. [all data]
Harrison and Moelwyn-Hughes, 1957
Harrison, D.; Moelwyn-Hughes, E.A.,
The heat capacities of certain liquids,
Proc. Roy. Soc. (London), 1957, A239, 230-246. [all data]
Staveley, Tupman, et al., 1955
Staveley, L.A.K.; Tupman, W.I.; Hart, K.R.,
Some thermodynamice properties of the systems benzene + ethylene dichloride, benzene + carbon tetrachloride, acetone + chloroform, and acetone + carbon disulphide,
Trans. Faraday Soc., 1955, 51, 323-342. [all data]
Kurbatov, 1948
Kurbatov, V.Ya.,
Heat capacity of liquids. 2. Heat capacity and the temperature dependence of heat capacity from halogen derivatives of acylic hydrocarbons,
Zh. Obshch. Kim., 1948, 18, 372-389. [all data]
Phillip, 1939
Phillip, N.M.,
Adiabatic and isothermal compressibilities of liquids,
Proc. Indian Acad. Sci., 1939, A9, 109-120. [all data]
Richards and Wallace, 1932
Richards, W.T.; Wallace, J.H., Jr.,
The specific heats of five organic liquids from their adiabatic temperature-pressure coefficients,
J. Am. Chem. Soc., 1932, 54, 2705-2713. [all data]
Williams and Daniels, 1925
Williams, J.W.; Daniels, F.,
The specific heats of binary mixtures,
J. Am. Chem. Soc., 1925, 47, 1490-1503. [all data]
Willams and Daniels, 1924
Willams, J.W.; Daniels, F.,
The specific heats of certain organic liquids at elevated temperatures,
J. Am. Chem. Soc., 1924, 46, 903-917. [all data]
Staneke, Groothuis, et al., 1995
Staneke, P.O.; Groothuis, G.; Ingemann, S.; Nibbering, N.M.M.,
Formation, stability and structure of radical anions of chloroform, tetrachloromethane and fluorotrichloromethane in the gas phase,
Int. J. Mass Spectrom. Ion Proc., 1995, 142, 1-2, 83, https://doi.org/10.1016/0168-1176(94)04127-S
. [all data]
Gaines, Kay, et al., 1966
Gaines, A.F.; Kay, J.; Page, F.M.,
Determination of Electron Affinities. Part 8. - CCl4, CHCl3, and CH2Cl2,
Trans. Farad. Soc., 1966, 62, 874, https://doi.org/10.1039/tf9666200874
. [all data]
Wang and Leroi, 1983
Wang, F.C.-Y.; Leroi, G.E.,
Photoionization and fragmentation of halogenated methanes,
Ann. Isr. Phys. Soc., 1983, 6, 210. [all data]
Von Niessen, Asbrink, et al., 1982
Von Niessen, W.; Asbrink, L.; Bieri, G.,
30.4 nm He(II) Photoelectron spectra of organic molecules. Part VI. Halogeno-compounds (C,H,X: X = Cl, Br, I),
J. Electron Spectrosc. Relat. Phenom., 1982, 26, 173. [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]
Werner, Tsai, et al., 1974
Werner, A.S.; Tsai, B.P.; Baer, T.,
Photoionization study of the ionization potentials fragmentation paths of the chlorinated methanes carbon tetrabromide,
J. Chem. Phys., 1974, 60, 3650. [all data]
Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D.,
Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation,
J. Chem. Phys., 1969, 50, 654. [all data]
Cermak, 1968
Cermak, V.,
Penning ionization electron spectroscopy. I. Determination of ionization potentials of polyatomic molecules,
Collection Czech. Chem. Commun., 1968, 33, 2739. [all data]
Watanabe, 1957
Watanabe, K.,
Ionization potentials of some molecules,
J. Chem. Phys., 1957, 26, 542. [all data]
Dixon, Murrell, et al., 1971
Dixon, R.N.; Murrell, J.N.; Narayan, B.,
The photoelectron spectra of the halomethanes,
Mol. Phys., 1971, 20, 611. [all data]
Reed and Snedden, 1956
Reed, R.I.; Snedden, W.,
Studies in electron impact methods. Part 6.-The formation of the methine and carbon ions,
J. Chem. Soc. Faraday Trans., 1956, 55, 876. [all data]
Hobrock and Kiser, 1964
Hobrock, D.L.; Kiser, R.W.,
Electron impact studies of some trihalomethanes: trichloromethane, dichlorofluoro-methane, chlorodifluoromethane, and trifluoromethane,
J. Phys. Chem., 1964, 68, 575. [all data]
Shapiro and Lossing, 1968
Shapiro, J.S.; Lossing, F.P.,
Free radicals by mass spectrometry. XXXVII. The ionization potential and heat of formation of dichlorocarbene,
J. Phys. Chem., 1968, 72, 1552. [all data]
Martin, Lampe, et al., 1966
Martin, R.H.; Lampe, F.W.; Taft, R.W.,
An electron-impact study of ionization and dissociation in methoxy- and halogen- substituted methanes,
J. Am. Chem. Soc., 1966, 88, 1353. [all data]
Ogawa, Miyoshi, et al., 1982
Ogawa, T.; Miyoshi, F.; Higo, M.,
Translational energy distribution and relative emission cross section of excited hydrogen atom produced in electron-chloroform collisions,
Bull. Chem. Soc. Jpn., 1982, 55, 1790. [all data]
Holmes, Lossing, et al., 1988
Holmes, J.L.; Lossing, F.P.; McFarlane, R.A.,
Stabilization energy and positional effects in halogen-substituted alkyl ions.,
Int. J. Mass Spectrom. Ion Phys., 1988, 86, 209. [all data]
Lossing, 1972
Lossing, F.P.,
Free radicals by mass spectrometry. XLIV. Ionization potentials bond dissociation energies for chloro-and fluoromethyl radicals,
Bull. Soc. Chim. Belg., 1972, 81, 125. [all data]
Harrison and Shannon, 1962
Harrison, A.G.; Shannon, T.W.,
An electron impact study of chloromethyl and dichloromethyl derivatives,
Can. J. Chem., 1962, 40, 1730. [all data]
Paulino and Squires, 1991
Paulino, J.A.; Squires, R.R.,
Carbene Thermochemistry from Collision-Induced Dissociation Threshold Energy Measurements - The Heats of Formation of X1A1 CF2 and X1A1 CCl2,
J. Am. Chem. Soc., 1991, 113, 15, 5573, https://doi.org/10.1021/ja00015a009
. [all data]
Bohme, Lee-Ruff, et al., 1972
Bohme, D.K.; Lee-Ruff, E.; Young, L.B.,
Acidity order of selected bronsted acids in the gas phase at 300K,
J. Am. Chem. Soc., 1972, 94, 5153. [all data]
Born, Ingemann, et al., 2000
Born, M.; Ingemann, S.; Nibbering, N.M.M.,
Thermochemical properties of halogen-substituted methanes, methyl radicals, and carbenes in the gas phase,
Int. J. Mass Spectrom., 2000, 194, 2-3, 103-113, https://doi.org/10.1016/S1387-3806(99)00125-6
. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
AE Appearance energy Cp,liquid Constant pressure heat capacity of liquid EA Electron affinity IE (evaluated) Recommended ionization energy S°gas,1 bar Entropy of gas at standard conditions (1 bar) ΔcH°liquid Enthalpy of combustion of liquid at standard conditions ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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