Propane, 2-chloro-2-methyl-

• Formula: C₄H₉Cl
• Molecular weight: 92.567
• IUPAC Standard InChI: InChI=1S/C4H9Cl/c1-4(2,3)5/h1-3H3 Copy

  
• IUPAC Standard InChIKey: NBRKLOOSMBRFMH-UHFFFAOYSA-N Copy
• 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
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
• Options:
  • Switch to calorie-based units

Data at NIST subscription sites:

• NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data)

NIST subscription sites provide data under the NIST Standard Reference Data Program, but require an annual fee to access. The purpose of the fee is to recover costs associated with the development of data collections included in such sites. Your institution may already be a subscriber. Follow the links above to find out more about the data in these sites and their terms of usage.

Gas phase thermochemistry data

Go To: Top, Phase change 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Phase change 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:
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

Enthalpy of vaporization

Antoine Equation Parameters

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

View plot Requires a JavaScript / HTML 5 canvas capable browser.

Enthalpy of fusion

Entropy of fusion

Enthalpy of phase transition

Entropy of phase transition

Gas phase ion energetics data

Go To: Top, Gas phase thermochemistry data, Phase change 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:
LL - Sharon G. Lias and Joel F. Liebman
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

References

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

Howlett, 1955
Howlett, K.E., The use of equilibrium constants to calculate thermodynamic quantities. Part II, J. Chem. Soc., 1955, 1784-17. [all data]

Dworkin and Guillamin, 1966
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]

Dworkin and Guillamin, 1966, 2
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]

Luo and Pacey, 1992
Luo, Y.-R.; Pacey, P.D., Effects of alkyl substitution on ionization energies of alkanes and haloalkanes and on heats of formation of their molecular cations. Part 2. Alkanes and chloro-, bromo- and iodoalkanes, Int. J. Mass Spectrom. Ion Processes, 1992, 112, 63. [all data]

Baldwin, Maccoll, et al., 1964
Baldwin, M.; Maccoll, A.; Miller, S.I., Appearance potentials of the lower chloroalkanes, J. Am. Chem. Soc., 1964, 86, 4498. [all data]

Watanabe, Nakayama, et al., 1962
Watanabe, K.; Nakayama, T.; Mottl, J., Ionization potentials of some molecules, J. Quant. Spectry. Radiative Transfer, 1962, 2, 369. [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]

Flamini, Semprini, et al., 1976
Flamini, A.; Semprini, E.; Stefani, F.; Sorriso, S.; Cardaci, G., He(I) photoelectron spectra and semiempirical molecular-orbital calculations on methylmetal halides of group 4A elements, J. Chem. Soc. Dalton Trans., 1976, 731. [all data]

Baldwin, Maccoll, et al., 1966
Baldwin, M.; Maccoll, A.; Miller, S.I., Ionization and appearance potentials from a study of alkyl chlorides, Advan. Mass Spectrom., 1966, 3, 259. [all data]

McLoughlin and Traeger, 1979
McLoughlin, R.G.; Traeger, J.C., Heat of formation for tert-butyl cation in the gas phase, J. Am. Chem. Soc., 1979, 101, 5791. [all data]

Notes

Go To: Top, Gas phase thermochemistry data, Phase change data, Gas phase ion energetics data, References

• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔHtrs	Enthalpy of phase transition
  ΔStrs	Entropy of phase transition
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
• The National Institute of Standards and Technology (NIST) uses its best efforts to deliver a high quality copy of the Database and to verify that the data contained therein have been selected on the basis of sound scientific judgment. However, NIST makes no warranties to that effect, and NIST shall not be liable for any damage that may result from errors or omissions in the Database.
• Customer support for NIST Standard Reference Data products.