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Propane, 2-chloro-2-methyl-

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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
Deltar16.6 ± 1.0kcal/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar14.3 ± 2.0kcal/molIMRELarson and McMahon, 1984gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar21.2cal/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
Deltar8.30 ± 0.20kcal/molTDAsLi, Ross, et al., 1996gas phase; B
Deltar8.0 ± 2.0kcal/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
Deltar17.7 ± 0.5kcal/molEqkHowlett, 1955gas phase; ALS
Deltar17.70kcal/molEqkHowlett, 1951gas phase; Hf-gas-(390) -44.4 kcal/mol; ALS
Deltar17.1 ± 0.5kcal/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
Deltar13.9 ± 1.0kcal/molTDAsLi, Ross, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar6.60 ± 0.20kcal/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
Deltar15.9 ± 1.0kcal/molTDAsLi, Ross, et al., 1996gas phase; B
Quantity Value Units Method Reference Comment
Deltar7.55 ± 0.20kcal/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
Deltar81.kcal/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; from t-C4H9+ + CH3Cl; Cox and Pilcher, 1970, 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-15.08 ± 0.42kcal/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° (kcal/mol) T (K) Method Reference Comment
13.7298.IMREMcMahon and Ohanessian, 2000Anchor alanine=39.89; RCD

References

Go To: Top, Reaction thermochemistry data, Notes

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

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

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]

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

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