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Methylene chloride

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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 as indicated in comments:
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Quantity Value Units Method Reference Comment
Deltafgas-95.52kJ/molReviewChase, 1998Data last reviewed in December, 1968
Deltafgas-95.1 ± 2.5kJ/molReviewManion, 2002derived from recommended «DELTA»fHliquid° and «DELTA»vapH°; DRB
Deltafgas-95.7 ± 1.3kJ/molChydLacher, Amador, et al., 1967Reanalyzed by Cox and Pilcher, 1970, Original value = -96.0 ± 1.3 kJ/mol; At 250 C; ALS
Quantity Value Units Method Reference Comment
gas,1 bar270.28J/mol*KReviewChase, 1998Data last reviewed in December, 1968

Gas Phase Heat Capacity (Shomate Equation)

Cp° = A + B*t + C*t2 + D*t3 + E/t2
H° − H°298.15= A*t + B*t2/2 + C*t3/3 + D*t4/4 − E/t + F − H
S° = A*ln(t) + B*t + C*t2/2 + D*t3/3 − E/(2*t2) + G
    Cp = heat capacity (J/mol*K)
    H° = standard enthalpy (kJ/mol)
    S° = standard entropy (J/mol*K)
    t = temperature (K) / 1000.

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Temperature (K) 298. - 1200.1200. - 6000.
A 19.1735195.12993
B 136.84446.721722
C -95.12993-1.288196
D 26.031050.085646
E -0.119405-14.93885
F -106.9338-157.3506
G 256.0144340.5412
H -95.52114-95.52114
ReferenceChase, 1998Chase, 1998
Comment Data last reviewed in December, 1968 Data last reviewed in December, 1968

Condensed phase thermochemistry data

Go To: Top, Gas 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:
DRB - Donald R. Burgess, Jr.
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-124.1 ± 2.5kJ/molReviewManion, 2002adopted combustion calorimetry data of Hu and Sinke, 1969 with increased uncertainty to reflect other data; DRB
Deltafliquid-124.3kJ/molCcrHu and Sinke, 1969, 2ALS
Quantity Value Units Method Reference Comment
Deltacliquid-602.50kJ/molCcrHu and Sinke, 1969, 2ALS
Deltacliquid-605.8 ± 8.4kJ/molCcbSmith, Bjellerup, et al., 1953Reanalyzed by Cox and Pilcher, 1970, Original value = -605. ± 4. kJ/mol; ALS
Quantity Value Units Method Reference Comment
liquid174.5J/mol*KN/AMoseeva, Rabinovich, et al., 1978DH

Constant pressure heat capacity of liquid

Cp,liquid (J/mol*K) Temperature (K) Reference Comment
102.3298.15Moseeva, Rabinovich, et al., 1978T = 5 to 300 K.; DH
105.5303.2Harrison and Moelwyn-Hughes, 1957T = 244 to 303 K. Unsmoothed experimental datum.; DH
129.3298.Kurbatov, 1948T = -76 to 41°C. Mean Cp, four temperatures.; DH
100.0298.Riedel, 1941T = -47 to 41°C.; DH
100.0298.1Riedel, 1940T = -47 to 41°C.; DH
100.5292.5Perlick, 1937T = -58 to 19°C. Value is unsmoothed experimental datum.; DH
100.8292.5Perlick, 1937, 2T = -58 to 19°C. Value is unsmoothed experimental datum.; DH

Reaction thermochemistry data

Go To: Top, Gas phase thermochemistry data, Condensed phase 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:
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, Gas phase thermochemistry data, Condensed phase thermochemistry 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.

Chase, 1998
Chase, M.W., Jr., NIST-JANAF Themochemical Tables, Fourth Edition, J. Phys. Chem. Ref. Data, Monograph 9, 1998, 1-1951. [all data]

Manion, 2002
Manion, J.A., Evaluated Enthalpies of Formation of the Stable Closed Shell C1 and C2 Chlorinated Hydrocarbons, J. Phys. Chem. Ref. Data, 2002, 31, 1, 123-172, https://doi.org/10.1063/1.1420703 . [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]

Hu and Sinke, 1969
Hu, A.T.; Sinke, G.C., Combustion calorimetry of some chlorinated organic compounds, J. Chem. Thermodyn., 1969, 1, 6, 507, https://doi.org/10.1016/0021-9614(69)90010-X . [all data]

Hu and Sinke, 1969, 2
Hu, A.T.; Sinke, G.C., Combustion calorimetry of some chlorinated organic compounds, J. Chem. Thermodyn., 1969, 1, 507-513. [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]

Moseeva, Rabinovich, et al., 1978
Moseeva, E.M.; Rabinovich, I.B.; Busygina, G.I.; Safonov, V.A.; Ovchinnikov, E.Yu., Thermodynamic proerties of methylene chloride, Termodin. Org. Soedin., Gor'kii, 1978, 1, 8-11. [all data]

Harrison and Moelwyn-Hughes, 1957
Harrison, D.; Moelwyn-Hughes, E.A., The heat capacities of certain liquids, Proc. Roy. Soc. (London), 1957, A239, 230-246. [all data]

Kurbatov, 1948
Kurbatov, V.Ya., Heat capacity of liquids. 2. Heat capacity and the temperature dependence of heat capacity from halogen derivatives of acylic hydrocarbons, Zh. Obshch. Kim., 1948, 18, 372-389. [all data]

Riedel, 1941
Riedel, L., Determination of the specific heat of liquid ethyl chloride and liquid methylene chloride, Bull. Int. Inst., Refrig. Annex 22, 1941, No4, 1-3. [all data]

Riedel, 1940
Riedel, L., Bestimmung der spezifischen Wärme von Äthychlorid und Methylenchlorid im flüssigen Zustand, Z. ges. Kalte-Ind., 1940, 47, 87. [all data]

Perlick, 1937
Perlick, A., Calorimetric investigations on dichloromethane, difluoromonochloroethane and tetrafluorodichloroethane, Bull. Int. Inst. Refrig., 1937, 18, 1-9. [all data]

Perlick, 1937, 2
Perlick, A., Kalorimetrische Messungen an Schwefeldioxyd, Methylenchlorid, Difluormonochloraethan und Tetrafluordichloraethan, Z. ges. Kalt-Ind., 1937, 44, 201-206. [all data]

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]

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

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References