Methylene chloride

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Reaction thermochemistry data

Go To: Top, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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
Δr1572. ± 9.2kJ/molG+TSBorn, Ingemann, et al., 2000gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B
Δr1567. ± 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
Δr1540. ± 8.4kJ/molIMREBorn, Ingemann, et al., 2000gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B
Δr1543.9 ± 2.9kJ/molIMREPoutsma, Paulino, et al., 1997gas phase; relative to tBuOH at ΔGacid = 369.3; B
Δr1535. ± 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 • Methylene chloride)

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

Quantity Value Units Method Reference Comment
Δr66.1 ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Δr61.9 ± 8.4kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B
Δr64.9 ± 1.3kJ/molTDEqDougherty, Dalton, et al., 1974gas phase; B,M
Quantity Value Units Method Reference Comment
Δr92.5J/mol*KN/ALarson and McMahon, 1984gas phase; switching reaction(Cl-)t-C4H9OH, Entropy change calculated or estimated; Kebarle, 1977; M
Δr92.0J/mol*KHPMSDougherty, Dalton, et al., 1974gas phase; M
Quantity Value Units Method Reference Comment
Δr38. ± 8.4kJ/molIMRELarson and McMahon, 1984gas phase; B,M
Δr37.0kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B
Δr37.2 ± 2.5kJ/molTDEqDougherty, Dalton, et al., 1974gas phase; B

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

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

Quantity Value Units Method Reference Comment
Δr68. ± 15.kJ/molIMRELarson and McMahon, 1987gas phase; B,M
Quantity Value Units Method Reference Comment
Δr101.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
Δr38. ± 9.6kJ/molIMRELarson and McMahon, 1987gas phase; B,M

C2H5+ + Methylene chloride = (C2H5+ • Methylene chloride)

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

Quantity Value Units Method Reference Comment
Δr151.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; Entropy change is questionable; M
Quantity Value Units Method Reference Comment
Δr189.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
Δr-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
Δr54.81kJ/molN/AHiraoka, Mizuno, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Δr27.4kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B

C2H4Cl5- + 3Methylene chloride = C3H6Cl7-

By formula: C2H4Cl5- + 3CH2Cl2 = C3H6Cl7-

Quantity Value Units Method Reference Comment
Δr40.6kJ/molN/AHiraoka, Mizuno, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Δr19.4kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B

C3H6Cl7- + 4Methylene chloride = C4H8Cl9-

By formula: C3H6Cl7- + 4CH2Cl2 = C4H8Cl9-

Quantity Value Units Method Reference Comment
Δr37.7kJ/molN/AHiraoka, Mizuno, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Δr15.2kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B

C4H8Cl9- + 5Methylene chloride = C5H10Cl11-

By formula: C4H8Cl9- + 5CH2Cl2 = C5H10Cl11-

Quantity Value Units Method Reference Comment
Δr32.2kJ/molN/AHiraoka, Mizuno, et al., 2001gas phase; B
Quantity Value Units Method Reference Comment
Δr11.0kJ/molTDAsHiraoka, Mizuno, et al., 2001gas phase; B

C3H7+ + Methylene chloride = (C3H7+ • Methylene chloride)

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

Quantity Value Units Method Reference Comment
Δr65.3kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr130.J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

C6H11+ + Methylene chloride = (C6H11+ • Methylene chloride)

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

Quantity Value Units Method Reference Comment
Δr44.4kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr130.J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

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

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

Quantity Value Units Method Reference Comment
Δr120.kJ/molICRStaley and Beauchamp, 1975gas phase; switching reaction(Li+)H2O, from graph; Dzidic and Kebarle, 1970 interpolated; M

C4H9+ + Methylene chloride = (C4H9+ • Methylene chloride)

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

Quantity Value Units Method Reference Comment
Δr40.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr93.3J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

C5H11+ + Methylene chloride = (C5H11+ • Methylene chloride)

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

Quantity Value Units Method Reference Comment
Δr40.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr97.5J/mol*KPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M

C5H9+ + Methylene chloride = (C5H9+ • Methylene chloride)

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

Quantity Value Units Method Reference Comment
Δr41.kJ/molPHPMSSharma, Meza de Hojer, et al., 1985gas phase; M
Quantity Value Units Method Reference Comment
Δr84.5J/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
Δr-37.7 ± 4.2kJ/molPACYang and Yang, 1992solvent: Heptane; MS

Henry's Law 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 by: Rolf Sander

Henry's Law constant (water solution)

kH(T) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 K)))
H = Henry's law constant for solubility in water at 298.15 K (mol/(kg*bar))
d(ln(kH))/d(1/T) = Temperature dependence constant (K)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.364100.LN/A 
0.41 MN/A 
0.383500.XN/A 
0.403800.MN/A 
0.403900.XN/A 
0.40 QN/A missing citation give several references for the Henry's law constants but don't assign them to specific species.
0.344300.XN/A 
0.473800.MGossett, 1987 
0.354200.XN/A 
0.394500.XN/A 
0.354200.MN/A 
0.313600.XN/A 
0.313700.XLeighton and Calo, 1981 
0.39 LN/A 
0.854200.XN/A 
0.40 VN/A 
1.2 VN/AValue at T = 275. K.
0.37 CN/A 
0.44 VN/A 
0.33 MPearson and McConnell, 1975The same data was also published in missing citation. Value at T = 293. K.
0.444100.MN/A 

Gas phase ion energetics 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 evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron
LL - Sharon G. Lias and Joel F. Liebman

Quantity Value Units Method Reference Comment
IE (evaluated)11.33 ± 0.04eVN/AN/AL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
628. ± 8.Cacace, de Petris, et al., 1999COS; C2H2. Paper reports PA although proton transfer reactivity brackets GB. Following authors, the GBs of CH2Cl2 and COS are equated given reversible proton transfer.; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
602. ± 8.Cacace, de Petris, et al., 1999COS; C2H2. Paper reports PA although proton transfer reactivity brackets GB. Following authors, the GBs of CH2Cl2 and COS are equated given reversible proton transfer.; MM

Ionization energy determinations

IE (eV) Method Reference Comment
11.32PEVon Niessen, Asbrink, et al., 1982LBLHLM
11.40PEKimura, Katsumata, et al., 1981LLK
11.32 ± 0.01PIWerner, Tsai, et al., 1974LLK
11.28EILossing, 1972LLK
11.33PEDewar and Worley, 1969RDSH
11.36CICermak, 1968RDSH
11.35 ± 0.02PIWatanabe, 1957RDSH
11.40PEDixon, Murrell, et al., 1971Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C+25.5 ± 0.1?EIReed and Snedden, 1956RDSH
CH+21.72 ± 0.04?EIReed and Snedden, 1956RDSH
CHCl2+13.00 ± 0.10HEIReed and Snedden, 1956RDSH
CH2+17.0Cl2EIHaney and Franklin, 1968RDSH
CH2Cl+12.10ClEIHolmes, Lossing, et al., 1988LL
CH2Cl+12.14 ± 0.02ClPIWerner, Tsai, et al., 1974LLK
CH2Cl+12.15ClEILossing, 1972LLK
CH2Cl+12.1 ± 0.1ClEIHarrison and Shannon, 1962RDSH
CH2Cl+12.89 ± 0.03ClEIReed and Snedden, 1956RDSH
CHC12+12.12 ± 0.05HEIMartin, Lampe, et al., 1966RDSH
Cl+17.4 ± 0.1CH2ClEIDeCorpo, Bafus, et al., 1971LLK
Cl+17.4CH2ClEIFranklin and Haney, 1970RDSH

De-protonation reactions

CHCl2- + Hydrogen cation = Methylene chloride

By formula: CHCl2- + H+ = CH2Cl2

Quantity Value Units Method Reference Comment
Δr1572. ± 9.2kJ/molG+TSBorn, Ingemann, et al., 2000gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B
Δr1567. ± 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
Δr1540. ± 8.4kJ/molIMREBorn, Ingemann, et al., 2000gas phase; D-EA from this reference yields BDE = 96.0±3.2 kcal/mol; B
Δr1543.9 ± 2.9kJ/molIMREPoutsma, Paulino, et al., 1997gas phase; relative to tBuOH at ΔGacid = 369.3; B
Δr1535. ± 13.kJ/molIMRBBohme, Lee-Ruff, et al., 1972gas phase; Comparable to DMSO; value altered from reference due to change in acidity scale; B

Mass spectrum (electron ionization)

Go To: Top, Reaction thermochemistry data, Henry's Law 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: NIST Mass Spectrometry Data Center, William E. Wallace, director

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Origin Japan AIST/NIMC Database- Spectrum MS-NW-5526
NIST MS number 228003

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References

Go To: Top, Reaction thermochemistry data, Henry's Law data, Gas phase ion energetics data, Mass spectrum (electron ionization), 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]

Gossett, 1987
Gossett, J.M., Measurement of Henry's Law Constants for C1 and C2 Chlorinated Hydrocarbons, Environ. Sci. Technol., 1987, 21, 202-208. [all data]

Leighton and Calo, 1981
Leighton, D.T.; Calo, J.M., Distribution Coefficients of Chlorinated Hydrocarbons in Dilute Air-Water Systems for Groundwater Contamination Applications, J. Chem. Eng. Data, 1981, 26, 382-385. [all data]

Pearson and McConnell, 1975
Pearson, C.R.; McConnell, G., Chlorinated C1 and C2 Hydrocarbons in the Marine Environment, Proc. R. Soc. London, B, 1975, 189, 305-332. [all data]

Cacace, de Petris, et al., 1999
Cacace, F.; de Petris, G.; Pepi, F.; Rosi, M.; Troiani, A., Gaseous [H3C-Cl-Cl](+) ions from the reaction of methane with Cl-3(+), the first example of a new dihalogenation process: Formation and characterization of CH3Cl2+ isomers by experimental and theoretical methods, Chemistry - A European Journal, 1999, 5, 2750. [all data]

Von Niessen, Asbrink, et al., 1982
Von Niessen, W.; Asbrink, L.; Bieri, G., 30.4 nm He(II) Photoelectron spectra of organic molecules. Part VI. Halogeno-compounds (C,H,X: X = Cl, Br, I), J. Electron Spectrosc. Relat. Phenom., 1982, 26, 173. [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]

Werner, Tsai, et al., 1974
Werner, A.S.; Tsai, B.P.; Baer, T., Photoionization study of the ionization potentials fragmentation paths of the chlorinated methanes carbon tetrabromide, J. Chem. Phys., 1974, 60, 3650. [all data]

Lossing, 1972
Lossing, F.P., Free radicals by mass spectrometry. XLIV. Ionization potentials bond dissociation energies for chloro-and fluoromethyl radicals, Bull. Soc. Chim. Belg., 1972, 81, 125. [all data]

Dewar and Worley, 1969
Dewar, M.J.S.; Worley, S.D., Photoelectron spectra of molecules. I. Ionization potentials of some organic molecules and their interpretation, J. Chem. Phys., 1969, 50, 654. [all data]

Cermak, 1968
Cermak, V., Penning ionization electron spectroscopy. I. Determination of ionization potentials of polyatomic molecules, Collection Czech. Chem. Commun., 1968, 33, 2739. [all data]

Watanabe, 1957
Watanabe, K., Ionization potentials of some molecules, J. Chem. Phys., 1957, 26, 542. [all data]

Dixon, Murrell, et al., 1971
Dixon, R.N.; Murrell, J.N.; Narayan, B., The photoelectron spectra of the halomethanes, Mol. Phys., 1971, 20, 611. [all data]

Reed and Snedden, 1956
Reed, R.I.; Snedden, W., Studies in electron impact methods. Part 6.-The formation of the methine and carbon ions, J. Chem. Soc. Faraday Trans., 1956, 55, 876. [all data]

Haney and Franklin, 1968
Haney, M.A.; Franklin, J.L., Correlation of excess energies of electron-impact dissociations with the translational energies of the products, J.Chem. Phys., 1968, 48, 4093. [all data]

Holmes, Lossing, et al., 1988
Holmes, J.L.; Lossing, F.P.; McFarlane, R.A., Stabilization energy and positional effects in halogen-substituted alkyl ions., Int. J. Mass Spectrom. Ion Phys., 1988, 86, 209. [all data]

Harrison and Shannon, 1962
Harrison, A.G.; Shannon, T.W., An electron impact study of chloromethyl and dichloromethyl derivatives, Can. J. Chem., 1962, 40, 1730. [all data]

Martin, Lampe, et al., 1966
Martin, R.H.; Lampe, F.W.; Taft, R.W., An electron-impact study of ionization and dissociation in methoxy- and halogen- substituted methanes, J. Am. Chem. Soc., 1966, 88, 1353. [all data]

DeCorpo, Bafus, et al., 1971
DeCorpo, J.J.; Bafus, D.A.; Franklin, J.L., Enthalpies of formation of the monohalomethyl radicals from mass spectrometric studies of the dihalomethanes, J. Chem. Thermodyn., 1971, 3, 125. [all data]

Franklin and Haney, 1970
Franklin, J.L.; Haney, M.A., Energy distribution in ionic decomposition processes, Recent Developments in Mass Spectroscopy, ed. K. Ogata and T. Hayakawa Baltimore Univ. Park Press, Baltimore, MD, 1970, 909. [all data]


Notes

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