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Methylene chloride

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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
MS - José A. Martinho Simões

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

CHCl2- + Hydrogen cation = Methylene chloride

By formula: CHCl2- + H+ = CH2Cl2

Quantity Value Units Method Reference Comment
Deltar1572. ± 9.2kJ/molG+TSBorn, Ingemann, et al., 2000gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B
Deltar1567. ± 13.kJ/molG+TSBohme, Lee-Ruff, et al., 1972gas phase; Comparable to DMSO; value altered from reference due to change in acidity scale; B
Quantity Value Units Method Reference Comment
Deltar1540. ± 8.4kJ/molIMREBorn, Ingemann, et al., 2000gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B
Deltar1543.9 ± 2.9kJ/molIMREPoutsma, Paulino, et al., 1997gas phase; relative to tBuOH at «DELTA»Gacid = 369.3; B
Deltar1535. ± 13.kJ/molIMRBBohme, Lee-Ruff, et al., 1972gas phase; Comparable to DMSO; value altered from reference due to change in acidity scale; B

Chlorine anion + Methylene chloride = (Chlorine anion bullet Methylene chloride)

By formula: Cl- + CH2Cl2 = (Cl- bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar66.1 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Deltar61.9 ± 8.4kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B
Deltar64.9 ± 1.3kJ/molTDEqDougherty, Dalton, et al., 1974gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar92.5J/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; Kebarle, 1977; M
Deltar92.0J/mol*KHPMSDougherty, Dalton, et al., 1974gas phase; M
Quantity Value Units Method Reference Comment
Deltar38. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Deltar37.0kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B
Deltar37.2 ± 2.5kJ/molTDEqDougherty, Dalton, et al., 1974gas phase; B

CN- + Methylene chloride = (CN- bullet Methylene chloride)

By formula: CN- + CH2Cl2 = (CN- bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar68. ± 15.kJ/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Deltar101.J/mol*KN/ALarson and McMahon, 1987gas phase; switching reaction,Thermochemical ladder(CN-)H2O, Entropy change calculated or estimated; Payzant, Yamdagni, et al., 1971; M
Quantity Value Units Method Reference Comment
Deltar38. ± 9.6kJ/molIMRELarson and McMahon, 1987gas phase; B,M

C2H5+ + Methylene chloride = (C2H5+ bullet Methylene chloride)

By formula: C2H5+ + CH2Cl2 = (C2H5+ bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar151.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; Entropy change is questionable; M
Quantity Value Units Method Reference Comment
Deltar189.J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; Entropy change is questionable; M

2Hydrogen + Methylene chloride = Methane + 2Hydrogen chloride

By formula: 2H2 + CH2Cl2 = CH4 + 2HCl

Quantity Value Units Method Reference Comment
Deltar-163.4 ± 1.3kJ/molChydLacher, Amador, et al., 1967gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -167.7 ± 1.3 kJ/mol; At 250 C; ALS

CH2Cl3- + 2Methylene chloride = C2H4Cl5-

By formula: CH2Cl3- + 2CH2Cl2 = C2H4Cl5-

Quantity Value Units Method Reference Comment
Deltar54.81kJ/molN/AHiraoka, Mizuno, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Deltar27.4kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B

C2H4Cl5- + 3Methylene chloride = C3H6Cl7-

By formula: C2H4Cl5- + 3CH2Cl2 = C3H6Cl7-

Quantity Value Units Method Reference Comment
Deltar40.6kJ/molN/AHiraoka, Mizuno, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Deltar19.4kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B

C3H6Cl7- + 4Methylene chloride = C4H8Cl9-

By formula: C3H6Cl7- + 4CH2Cl2 = C4H8Cl9-

Quantity Value Units Method Reference Comment
Deltar37.7kJ/molN/AHiraoka, Mizuno, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Deltar15.2kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B

C4H8Cl9- + 5Methylene chloride = C5H10Cl11-

By formula: C4H8Cl9- + 5CH2Cl2 = C5H10Cl11-

Quantity Value Units Method Reference Comment
Deltar32.2kJ/molN/AHiraoka, Mizuno, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Deltar11.0kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B

C3H7+ + Methylene chloride = (C3H7+ bullet Methylene chloride)

By formula: C3H7+ + CH2Cl2 = (C3H7+ bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar65.3kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar130.J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

C6H11+ + Methylene chloride = (C6H11+ bullet Methylene chloride)

By formula: C6H11+ + CH2Cl2 = (C6H11+ bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar44.4kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar130.J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

Lithium ion (1+) + Methylene chloride = (Lithium ion (1+) bullet Methylene chloride)

By formula: Li+ + CH2Cl2 = (Li+ bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar120.kJ/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 interpolated; M

C4H9+ + Methylene chloride = (C4H9+ bullet Methylene chloride)

By formula: C4H9+ + CH2Cl2 = (C4H9+ bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar40.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar93.3J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

C5H11+ + Methylene chloride = (C5H11+ bullet Methylene chloride)

By formula: C5H11+ + CH2Cl2 = (C5H11+ bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar40.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar97.5J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

C5H9+ + Methylene chloride = (C5H9+ bullet Methylene chloride)

By formula: C5H9+ + CH2Cl2 = (C5H9+ bullet CH2Cl2)

Quantity Value Units Method Reference Comment
Deltar41.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Deltar84.5J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

C14H21MnO2 (solution) + Methylene chloride (solution) = C8H7Cl2MnO2 (solution) + Heptane (solution)

By formula: C14H21MnO2 (solution) + CH2Cl2 (solution) = C8H7Cl2MnO2 (solution) + C7H16 (solution)

Quantity Value Units Method Reference Comment
Deltar-37.7 ± 4.2kJ/molPACYang and Yang, 1992solvent: Heptane; MS

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.

Born, Ingemann, et al., 2000
Born, M.; Ingemann, S.; Nibbering, N.M.M., Thermochemical properties of halogen-substituted methanes, methyl radicals, and carbenes in the gas phase, Int. J. Mass Spectrom., 2000, 194, 2-3, 103-113, https://doi.org/10.1016/S1387-3806(99)00125-6 . [all data]

Bohme, Lee-Ruff, et al., 1972
Bohme, D.K.; Lee-Ruff, E.; Young, L.B., Acidity order of selected bronsted acids in the gas phase at 300K, J. Am. Chem. Soc., 1972, 94, 5153. [all data]

Poutsma, Paulino, et al., 1997
Poutsma, J.C.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of CHCl, CHF, and CClF. A Gas-Phase Experimental and G2 Theoretical Study., J. Phys. Chem. A, 1997, 101, 29, 5327, https://doi.org/10.1021/jp970778f . [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]

Hiraoka, Mizuno, et al., 2001
Hiraoka, K.; Mizuno, T.; Iino, T.; Eguchi, D.; Yamabe, S., Characteristic changes of bond energies for gas-phase cluster ions of halide ions with methane and chloromethanes, J. Phys. Chem. A, 2001, 105, 20, 4887-4893, https://doi.org/10.1021/jp010143n . [all data]

Dougherty, Dalton, et al., 1974
Dougherty, R.C.; Dalton, J.; Roberts, J.D., SN2 reactions in the gas phase: Structure of the transition state, Org. Mass Spectrom., 1974, 8, 77. [all data]

Kebarle, 1977
Kebarle, P., Ion Thermochemistry and Solvation from Gas Phase Ion Equilibria, Ann. Rev. Phys. Chem., 1977, 28, 1, 445, https://doi.org/10.1146/annurev.pc.28.100177.002305 . [all data]

Larson and McMahon, 1987
Larson, J.W.; McMahon, T.B., Hydrogen bonding in gas phase anions. The energetics of interaction between cyanide ion and bronsted acids, J. Am. Chem. Soc., 1987, 109, 6230. [all data]

Payzant, Yamdagni, et al., 1971
Payzant, J.D.; Yamdagni, R.; Kebarle, P., Hydration of CN-, NO2-, NO3-, and HO- in the gas phase, Can. J. Chem., 1971, 49, 3308. [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]

Lacher, Amador, et al., 1967
Lacher, J.R.; Amador, A.; Park, J.D., Reaction heats of organic compounds. Part 5.-Heats of hydrogenation of dichloromethane, 1,1- and 1,2-dichloroethane and 1,2-dichloropropane, Trans. Faraday Soc., 1967, 63, 1608-1611. [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]

Staley and Beauchamp, 1975
Staley, R.H.; Beauchamp, J.L., Intrinsic Acid - Base Properties of Molecules. Binding Energies of Li+ to pi - and n - Donor Bases, J. Am. Chem. Soc., 1975, 97, 20, 5920, https://doi.org/10.1021/ja00853a050 . [all data]

Dzidic and Kebarle, 1970
Dzidic, I.; Kebarle, P., Hydration of the Alkali Ions in the Gas Phase. Enthalpies and Entropies of Reactions M+(H2O)n-1 + H2O = M+(H2O)n, J. Phys. Chem., 1970, 74, 7, 1466, https://doi.org/10.1021/j100702a013 . [all data]

Yang and Yang, 1992
Yang, P.-F.; Yang, K.G., J. Am. Chem. Soc., 1992, 114, 6937. [all data]


Notes

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