Propane, 2-chloro-2-methyl-
- Formula: C4H9Cl
- Molecular weight: 92.567
- IUPAC Standard InChIKey: NBRKLOOSMBRFMH-UHFFFAOYSA-N
- CAS Registry Number: 507-20-0
- 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: tert-Butyl Chloride; Trimethylchloromethane; 2-Chloro-2-methylpropane; 2-Chloroisobutane; 2-Methyl-2-chloropropane; 2-Methyl-2-propyl chloride; tert-C4H9Cl; Chlorotrimethylmethane; Tertiary-butyl chloride; NSC 6527
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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -179.9 | kJ/mol | Eqk | Howlett, 1955 |
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 |
---|---|---|---|---|---|
ΔfH°liquid | -211.2 ± 2.3 | kJ/mol | Cm | Arnett and Pienta, 1980 | Hydrochlorination; ALS |
Quantity | Value | Units | Method | Reference | Comment |
ΔcH°liquid | -2675.2 ± 8.4 | kJ/mol | Ccb | Smith, Bjellerup, et al., 1953 | Reanalyzed by Cox and Pilcher, 1970, Original value = -2670. ± 8. kJ/mol; ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
162.0 | 298.15 | Shehatta, 1993 | DH |
172.80 | 272.73 | Dworkin and Guillamin, 1966 | T = 82 to 273 K. Value is unsmoothed experimental datum.; DH |
152.7 | 259.6 | Kushner, Crowe, et al., 1950 | T = 122 to 260 K. Value is unsmoothed experimental datum.; 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, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
CAL - James S. Chickos, William E. Acree, Jr., Joel F. Liebman, Students of Chem 202 (Introduction to the Literature of Chemistry), University of Missouri -- St. Louis
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 324.1 ± 0.9 | K | AVG | N/A | Average of 14 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 247. ± 3. | K | AVG | N/A | Average of 8 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Ttriple | 247.53 | K | N/A | Dworkin and Guillamin, 1966, 2 | Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 29.19 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 28.6 | kJ/mol | CGC | Chickos, Hosseini, et al., 1995 | Based on data from 313. to 353. K.; AC |
ΔvapH° | 29.0 ± 0.1 | kJ/mol | C | Wadsö, Luoma, et al., 1968 | AC |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
27.55 | 324. | N/A | Majer and Svoboda, 1985 | |
32.3 | 268. | A | Stephenson and Malanowski, 1987 | Based on data from 253. to 358. K. See also Dykyj, 1971.; AC |
27.8 | 309. | A | Stephenson and Malanowski, 1987 | Based on data from 295. to 323. K. See also Calero, Valle, et al., 1969.; AC |
27. | 310. | N/A | Calero, Valle, et al., 1969 | Based on data from 295. to 323. K. See also Boublik, Fried, et al., 1984.; AC |
29.1 | 269. | N/A | Stull, 1947 | Based on data from 254. to 324. 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 | Comment |
---|---|---|---|---|---|
295. to 319.71 | 1.0542 | 110.567 | -221.514 | Calero, Valle, et al., 1969, 2 | Coefficents calculated by NIST from author's data. |
254. to 324. | 4.24201 | 1281.242 | -21.795 | Stull, 1947 | Coefficents calculated by NIST from author's data. |
Enthalpy of fusion
ΔfusH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
1.89 | 247.8 | DSC | Tamarit, López, et al., 2000 | AC |
1.97 | 248.1 | N/A | Lange, 1985 | AC |
1.99 | 248.4 | N/A | Urban, Janik, et al., 1972 | AC |
Entropy of fusion
ΔfusS (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
10.25 | 182.9 | Dean, 1985 | CAL |
26.82 | 219.3 | ||
7.95 | 248.1 |
Enthalpy of phase transition
ΔHtrs (kJ/mol) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
1.874 | 182.91 | crystaline, III | crystaline, II | Dworkin and Guillamin, 1966 | DH |
5.883 | 219.25 | crystaline, II | crystaline, I | Dworkin and Guillamin, 1966 | DH |
2.071 | 247.53 | crystaline, I | liquid | Dworkin and Guillamin, 1966 | DH |
1.715 | 183.1 | crystaline, III | crystaline, II | Kushner, Crowe, et al., 1950 | DH |
5.815 | 219.6 | crystaline, II | crystaline, I | Kushner, Crowe, et al., 1950 | DH |
2.010 | 248.1 | crystaline, I | liquid | Kushner, Crowe, et al., 1950 | DH |
Entropy of phase transition
ΔStrs (J/mol*K) | Temperature (K) | Initial Phase | Final Phase | Reference | Comment |
---|---|---|---|---|---|
10.25 | 182.91 | crystaline, III | crystaline, II | Dworkin and Guillamin, 1966 | DH |
26.83 | 219.25 | crystaline, II | crystaline, I | Dworkin and Guillamin, 1966 | DH |
8.37 | 247.53 | crystaline, I | liquid | Dworkin and Guillamin, 1966 | DH |
9.4 | 183.1 | crystaline, III | crystaline, II | Kushner, Crowe, et al., 1950 | DH |
26.5 | 219.6 | crystaline, II | crystaline, I | Kushner, Crowe, et al., 1950 | DH |
8.1 | 248.1 | crystaline, I | liquid | Kushner, Crowe, et al., 1950 | DH |
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
M - Michael M. Meot-Ner (Mautner) and Sharon G. Lias
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
RCD - Robert C. Dunbar
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
By formula: Cl- + C4H9Cl = (Cl- • C4H9Cl)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 69.5 ± 4.2 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
ΔrH° | 59.8 ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 88.7 | J/mol*K | N/A | Larson and McMahon, 1984 | gas phase; switching reaction(Cl-)t-C4H9F, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 34.7 ± 0.84 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
ΔrG° | 33. ± 8.4 | kJ/mol | IMRE | Larson and McMahon, 1984 | gas phase; B,M |
By formula: C4H9Cl = C4H8 + HCl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 74. ± 2. | kJ/mol | Eqk | Howlett, 1955 | gas phase; ALS |
ΔrH° | 74.06 | kJ/mol | Eqk | Howlett, 1951 | gas phase; Hf-gas-(390) -44.4 kcal/mol; ALS |
ΔrH° | 72. ± 2. | kJ/mol | Eqk | Kistiakowsky and Stauffer, 1937 | gas phase; ALS |
By formula: Br- + C4H9Cl = (Br- • C4H9Cl)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 58.2 ± 4.2 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 27.6 ± 0.84 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
By formula: CN- + C4H9Cl = (CN- • C4H9Cl)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 66.5 ± 4.2 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 31.6 ± 0.84 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
By formula: CH3+ + C4H9Cl = (CH3+ • C4H9Cl)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 340. | kJ/mol | PHPMS | Sharma, Meza de Hojer, et al., 1985 | gas phase; from t-C4H9+ + CH3Cl; Cox and Pilcher, 1970, 2, Rosenstock, Buff, et al., 1982; M |
By formula: C4H8 + HCl = C4H9Cl
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -63.1 ± 1.8 | kJ/mol | Cm | Arnett and Pienta, 1980 | liquid phase; solvent: Methylene chloride; Hydrochloronation; ALS |
By formula: Na+ + C4H9Cl = (Na+ • C4H9Cl)
Free energy of reaction
ΔrG° (kJ/mol) | T (K) | Method | Reference | Comment |
---|---|---|---|---|
57.3 | 298. | IMRE | McMahon and Ohanessian, 2000 | Anchor alanine=39.89; RCD |
IR Spectrum
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, References, Notes
Data compiled by: Coblentz Society, Inc.
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Howlett, 1955
Howlett, K.E.,
The use of equilibrium constants to calculate thermodynamic quantities. Part II,
J. Chem. Soc., 1955, 1784-17. [all data]
Arnett and Pienta, 1980
Arnett, E.M.; Pienta, N.J.,
Stabilities of carbonium ions in solution. 12. Heats of formation of alkyl chlorides as an entree to heats of solvation of aliphatic carbonium ions,
J. Am. Chem. Soc., 1980, 102, 3329-3334. [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]
Shehatta, 1993
Shehatta, I.,
Heat capacity at constant pressure of some halogen compounds,
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Dworkin and Guillamin, 1966
Dworkin, A.; Guillamin, M.,
Chaleur specifique du chlorure de tertiobutyle a basse temperature,
J. chim. Phys. physicochim., 1966, 63, 53-58. [all data]
Kushner, Crowe, et al., 1950
Kushner, L.M.; Crowe, R.W.; Smyth, C.P.,
The heat capacities and dielectric constants of some alkyl halides in the solid state,
J. Am. Chem. Soc., 1950, 72, 1091-1098. [all data]
Dworkin and Guillamin, 1966, 2
Dworkin, A.; Guillamin, M.,
Specific heat of tert-butyl chloride at low temperature,
J. Chim. Phys. Phys.-Chim. Biol., 1966, 63, 53. [all data]
Majer and Svoboda, 1985
Majer, V.; Svoboda, V.,
Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]
Chickos, Hosseini, et al., 1995
Chickos, James S.; Hosseini, Sarah; Hesse, Donald G.,
Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times,
Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3
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Wadsö, Luoma, et al., 1968
Wadsö, Ingemar; Luoma, Sinikka; Olson, Thomas; Norin, Torbjörn,
Heats of Vaporization of Organic Compounds. II. Chlorides, Bromides, and Iodides.,
Acta Chem. Scand., 1968, 22, 2438-2444, https://doi.org/10.3891/acta.chem.scand.22-2438
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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]
Dykyj, 1971
Dykyj, J.,
Petrochemia, 1971, 11, 2, 27. [all data]
Calero, Valle, et al., 1969
Calero, G.C.; Valle, M.M.; Losa, C.G.,
Rev. Acad. Cienc. Fis. Quim. Nat. Zaragoza, 1969, 24, 2, 137. [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]
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]
Calero, Valle, et al., 1969, 2
Calero, G.C.; Valle, M.M.; Losa, C.G.,
Estudio Termodinamico del Sistema 2-Cloro, 2-Metilpropano 2-Bromo, 2-Metilpropano,
Rev. Acad. Cienc. Exactas Fis. Quim. Nat. Zaragoza, 1969, 24, 2, 137-158. [all data]
Tamarit, López, et al., 2000
Tamarit, J.Ll.; López, D.O.; Alcobé, X.; Barrio, M.; Salud, J.; Pardo, L.C.,
Thermal and Structural Characterization of (CH 3 ) 3 CCl,
Chem. Mater., 2000, 12, 2, 555-563, https://doi.org/10.1021/cm9911565
. [all data]
Lange, 1985
Lange, N.A.,
Lange's Handbook of Chemistry, 13th Edition, J.A. Dean, ed(s)., McGraw-Hill, New York, NY, 1985, 1792. [all data]
Urban, Janik, et al., 1972
Urban, S.; Janik, J.A.; Lenik, J.; Mayer, J.; Waluga, T.; Wróbel, S.,
Calorimetric, dielectric, and infrared investigations of solid t-butyl chloride,
Phys. Stat. Sol. (a), 1972, 10, 1, 271-280, https://doi.org/10.1002/pssa.2210100132
. [all data]
Dean, 1985
Dean, J.A.,
Lange's Handbook of Chemistry, 1985, McGraw-Hill. [all data]
Li, Ross, et al., 1996
Li, C.; Ross, P.; Szulejko, J.; McMahon, T.B.,
High-Pressure Mass Spectrometric Investigations of the Potential Energy Surfaces of Gas-Phase Sn2 Reactions.,
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Larson and McMahon, 1984
Larson, J.W.; McMahon, T.B.,
Hydrogen bonding in gas phase anions. An experimental investigation of the interaction between chloride ion and bronsted acids from ICR chloride exchange equilibria,
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Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B.,
Gas phase negative ion chemistry of alkylchloroformates,
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Howlett, 1951
Howlett, K.E.,
The use of equilibrium constants to calculate thermodynamic quantities. Part I. Equilibria in the system tert.-butyl chloride, isobutene, hydrogen chloride,
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Kistiakowsky and Stauffer, 1937
Kistiakowsky, G.B.; Stauffer, C.H.,
The kinetics of gaseous addition of halogen acids to isobutene, 1937, 165-170. [all data]
Sharma, Meza de Hojer, et al., 1985
Sharma, D.M.S.; Meza de Hojer, S.; Kebarle, P.,
Stabilities of halonium ions from a study of gas-phase equilibria R+ + XR' = (RXR')+,
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. [all data]
Cox and Pilcher, 1970, 2
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds
in Academic Press, New York, 1970. [all data]
Rosenstock, Buff, et al., 1982
Rosenstock, H.M.; Buff, R.; Ferreira, M.A.A.; Lias, S.G.; Parr, A.C.; Stockbauer, R.L.; Holmes, J.L.,
Fragmentation mechanism and energetics of some alkyl halide ions,
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McMahon and Ohanessian, 2000
McMahon, T.B.; Ohanessian, G.,
An Experimental and Ab Initio Study of the Nature of the Binding in Gas-Phase Complexes of Sodium Ions,
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. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, IR Spectrum, References
- Symbols used in this document:
Cp,liquid Constant pressure heat capacity of liquid T Temperature Tboil Boiling point Tfus Fusion (melting) point Ttriple Triple point temperature ΔHtrs Enthalpy of phase transition ΔStrs Entropy of phase transition 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 ΔfusH Enthalpy of fusion ΔfusS Entropy of fusion ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔrS° Entropy of reaction 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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