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Propane, 2-chloro-2-methyl-

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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

Quantity Value Units Method Reference Comment
Deltafgas-179.9kJ/molEqkHowlett, 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
Deltafliquid-211.2 ± 2.3kJ/molCmArnett and Pienta, 1980Hydrochlorination; ALS
Quantity Value Units Method Reference Comment
Deltacliquid-2675.2 ± 8.4kJ/molCcbSmith, Bjellerup, et al., 1953Reanalyzed 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
162.0298.15Shehatta, 1993DH
172.80272.73Dworkin and Guillamin, 1966T = 82 to 273 K. Value is unsmoothed experimental datum.; DH
152.7259.6Kushner, Crowe, et al., 1950T = 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
Tboil324.1 ± 0.9KAVGN/AAverage of 14 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus247. ± 3.KAVGN/AAverage of 8 values; Individual data points
Quantity Value Units Method Reference Comment
Ttriple247.53KN/ADworkin and Guillamin, 1966, 2Crystal phase 1 phase; Uncertainty assigned by TRC = 0.02 K; TRC
Quantity Value Units Method Reference Comment
Deltavap29.19kJ/molN/AMajer and Svoboda, 1985 
Deltavap28.6kJ/molCGCChickos, Hosseini, et al., 1995Based on data from 313. - 353. K.; AC
Deltavap29.0 ± 0.1kJ/molCWadsö, Luoma, et al., 1968AC

Enthalpy of vaporization

DeltavapH (kJ/mol) Temperature (K) Method Reference Comment
27.55324.N/AMajer and Svoboda, 1985 
32.3268.AStephenson and Malanowski, 1987Based on data from 253. - 358. K. See also Dykyj, 1971.; AC
27.8309.AStephenson and Malanowski, 1987Based on data from 295. - 323. K. See also Calero, Valle, et al., 1969.; AC
27.310.N/ACalero, Valle, et al., 1969Based on data from 295. - 323. K. See also Boublik, Fried, et al., 1984.; AC
29.1269.N/AStull, 1947Based on data from 254. - 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. - 319.711.0542110.567-221.514Calero, Valle, et al., 1969, 2Coefficents calculated by NIST from author's data.
254. - 324.4.242011281.242-21.795Stull, 1947Coefficents calculated by NIST from author's data.

Enthalpy of fusion

DeltafusH (kJ/mol) Temperature (K) Method Reference Comment
1.89247.8DSCTamarit, López, et al., 2000AC
1.97248.1N/ALange, 1985AC
1.99248.4N/AUrban, Janik, et al., 1972AC

Entropy of fusion

DeltafusS (J/mol*K) Temperature (K) Reference Comment
10.25182.9Dean, 1985CAL
26.82219.3
7.95248.1

Enthalpy of phase transition

DeltaHtrs (kJ/mol) Temperature (K) Initial Phase Final Phase Reference Comment
1.874182.91crystaline, IIIcrystaline, IIDworkin and Guillamin, 1966DH
5.883219.25crystaline, IIcrystaline, IDworkin and Guillamin, 1966DH
2.071247.53crystaline, IliquidDworkin and Guillamin, 1966DH
1.715183.1crystaline, IIIcrystaline, IIKushner, Crowe, et al., 1950DH
5.815219.6crystaline, IIcrystaline, IKushner, Crowe, et al., 1950DH
2.010248.1crystaline, IliquidKushner, Crowe, et al., 1950DH

Entropy of phase transition

DeltaStrs (J/mol*K) Temperature (K) Initial Phase Final Phase Reference Comment
10.25182.91crystaline, IIIcrystaline, IIDworkin and Guillamin, 1966DH
26.83219.25crystaline, IIcrystaline, IDworkin and Guillamin, 1966DH
8.37247.53crystaline, IliquidDworkin and Guillamin, 1966DH
9.4183.1crystaline, IIIcrystaline, IIKushner, Crowe, et al., 1950DH
26.5219.6crystaline, IIcrystaline, IKushner, Crowe, et al., 1950DH
8.1248.1crystaline, IliquidKushner, Crowe, et al., 1950DH

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 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

Chlorine anion + Propane, 2-chloro-2-methyl- = (Chlorine anion bullet Propane, 2-chloro-2-methyl-)

By formula: Cl- + C4H9Cl = (Cl- bullet C4H9Cl)

Quantity Value Units Method Reference Comment
Deltar69.5 ± 4.2kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar59.8 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar88.7J/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)t-C4H9F, Entropy change calculated or estimated; Larson and McMahon, 1984, 2; M
Quantity Value Units Method Reference Comment
Deltar34.7 ± 0.84kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar33. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M

Propane, 2-chloro-2-methyl- = 1-Propene, 2-methyl- + Hydrogen chloride

By formula: C4H9Cl = C4H8 + HCl

Quantity Value Units Method Reference Comment
Deltar74. ± 2.kJ/molEqkHowlett, 1955gas phase; ALS
Deltar74.06kJ/molEqkHowlett, 1951gas phase; Hf-gas-(390) -44.4 kcal/mol; ALS
Deltar72. ± 2.kJ/molEqkKistiakowsky and Stauffer, 1937gas phase; ALS

Bromine anion + Propane, 2-chloro-2-methyl- = (Bromine anion bullet Propane, 2-chloro-2-methyl-)

By formula: Br- + C4H9Cl = (Br- bullet C4H9Cl)

Quantity Value Units Method Reference Comment
Deltar58.2 ± 4.2kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar27.6 ± 0.84kJ/molTDAsLi, Ross, et al., 1996gas phase; B

CN- + Propane, 2-chloro-2-methyl- = (CN- bullet Propane, 2-chloro-2-methyl-)

By formula: CN- + C4H9Cl = (CN- bullet C4H9Cl)

Quantity Value Units Method Reference Comment
Deltar66.5 ± 4.2kJ/molTDAsLi, Ross, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar31.6 ± 0.84kJ/molTDAsLi, Ross, et al., 1996gas phase; B

Methyl cation + Propane, 2-chloro-2-methyl- = (Methyl cation bullet Propane, 2-chloro-2-methyl-)

By formula: CH3+ + C4H9Cl = (CH3+ bullet C4H9Cl)

Quantity Value Units Method Reference Comment
Deltar340.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; from t-C4H9+ + CH3Cl; Cox and Pilcher, 1970, 2, Rosenstock, Buff, et al., 1982; M

1-Propene, 2-methyl- + Hydrogen chloride = Propane, 2-chloro-2-methyl-

By formula: C4H8 + HCl = C4H9Cl

Quantity Value Units Method Reference Comment
Deltar-63.1 ± 1.8kJ/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochloronation; ALS

Sodium ion (1+) + Propane, 2-chloro-2-methyl- = (Sodium ion (1+) bullet Propane, 2-chloro-2-methyl-)

By formula: Na+ + C4H9Cl = (Na+ bullet C4H9Cl)

Free energy of reaction

DeltarG° (kJ/mol) T (K) Method Reference Comment
57.3298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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, 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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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 107667

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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.

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, Thermochim. Acta, 1993, 213, 1-10. [all data]

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 . [all data]

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 . [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]

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., J. Am. Chem. Soc., 1996, 118, 39, 9360, https://doi.org/10.1021/ja960565o . [all data]

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, J. Am. Chem. Soc., 1984, 106, 517. [all data]

Larson and McMahon, 1984, 2
Larson, J.W.; McMahon, T.B., Gas phase negative ion chemistry of alkylchloroformates, Can. J. Chem., 1984, 62, 675. [all data]

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, J. Chem. Soc., 1951, 1409-1412. [all data]

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')+, J. Am. Chem. Soc., 1985, 107, 13, 3757, https://doi.org/10.1021/ja00299a002 . [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, J. Am. Chem. Soc., 1982, 104, 2337. [all data]

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, Chem. Eur. J., 2000, 6, 16, 2931, https://doi.org/10.1002/1521-3765(20000818)6:16<2931::AID-CHEM2931>3.0.CO;2-7 . [all data]


Notes

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