Butane, 2-chloro-2-methyl-

Data at NIST subscription sites:

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.


Condensed phase thermochemistry data

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

Quantity Value Units Method Reference Comment
Δfliquid-235. ± 2.kJ/molCmArnett and Pienta, 1980Hydrochlorination
Quantity Value Units Method Reference Comment
Δcliquid-3327.5 ± 8.4kJ/molCcbSmith, Bjellerup, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -3322. ± 8. kJ/mol

Phase change data

Go To: Top, Condensed phase thermochemistry data, Reaction 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 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Tboil358.8KN/AWeast and Grasselli, 1989BS
Tboil358.KN/AKornblum, Smiley, et al., 1955Uncertainty assigned by TRC = 2. K; TRC
Tboil358.15KN/AKharasch and Buchi, 1951Uncertainty assigned by TRC = 2. K; TRC
Tboil358.75KN/AMumford and Phillips, 1950Uncertainty assigned by TRC = 0.5 K; TRC
Tboil358.8KN/ATimmermans, 1921Uncertainty assigned by TRC = 0.2 K; TRC
Quantity Value Units Method Reference Comment
Tfus200.KN/AFleming and Whitmore, 1932Uncertainty assigned by TRC = 5. K; TRC
Tfus200.45KN/ATimmermans, 1921Uncertainty assigned by TRC = 0.5 K; TRC

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
35.0295.AStephenson and Malanowski, 1987Based on data from 280. to 396. K. See also Dykyj, 1972.; AC
33.5 ± 0.84356.2VMathews and Fehlandt, 1931Reanalyzed by Pedley, Naylor, et al., 1986, Original value = 30.7 kJ/mol; ALS

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

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

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

Butane, 2-chloro-2-methyl- = Butane, 2-chloro-3-methyl-

By formula: C5H11Cl = C5H11Cl

Quantity Value Units Method Reference Comment
Δr9.12kJ/molEqkEsipenok, Kabo, et al., 1973liquid phase; solvent: liquid phase
Δr7.9 ± 0.2kJ/molEqkEsipenok, Kabo, et al., 1973liquid phase; solvent: cyclohexane

2-Butene, 2-methyl- + Hydrogen chloride = Butane, 2-chloro-2-methyl-

By formula: C5H10 + HCl = C5H11Cl

Quantity Value Units Method Reference Comment
Δr-59.08 ± 0.92kJ/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochloroination

2-Methyl-1-butene + Hydrogen chloride = Butane, 2-chloro-2-methyl-

By formula: C5H10 + HCl = C5H11Cl

Quantity Value Units Method Reference Comment
Δr-63.7 ± 1.4kJ/molCmArnett and Pienta, 1980liquid phase; solvent: Methylene chloride; Hydrochlorination

References

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

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

Kornblum, Smiley, et al., 1955
Kornblum, N.; Smiley, R.A.; Ungnade, H.E.; White, A.M.; Taub, B., The reaction of silver nitrite with secondary and tertiary alkyl halides, J. Am. Chem. Soc., 1955, 77, 5528-33. [all data]

Kharasch and Buchi, 1951
Kharasch, M.S.; Buchi, G., Reactions of Atoms and Free Radicals in Solution XXIV. The Reactions of Acetyl Peroxide with Chloro- and Dichloroalkanes, J. Am. Chem. Soc., 1951, 73, 632. [all data]

Mumford and Phillips, 1950
Mumford, S.A.; Phillips, J.W.C., 19. The Physical Properties of Some Aliphatic Compounds, J. Chem. Soc., 1950, 1950, 75-84. [all data]

Timmermans, 1921
Timmermans, J., The Freezing Points of Organic Substances IV. New Exp. Determinations, Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]

Fleming and Whitmore, 1932
Fleming, G.H.; Whitmore, F.C., Chlorination of Neopentane, J. Am. Chem. Soc., 1932, 54, 3460. [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, 1972
Dykyj, J., Petrochemia, 1972, 12, 1, 13. [all data]

Mathews and Fehlandt, 1931
Mathews, J.H.; Fehlandt, P.R., The heats of vaporization of some organic compounds, J. Am. Chem. Soc., 1931, 53, 3212-32. [all data]

Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P., Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]

Esipenok, Kabo, et al., 1973
Esipenok, G.E.; Kabo, G.Ya.; Andreevskii, D.N., Equilibrium and thermodynamics of the isomerisation of methylchlorobutanes, Russ. J. Phys. Chem. (Engl. Transl.), 1973, 47, 420. [all data]


Notes

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