Chloromethane

• Formula: CH₃Cl
• Molecular weight: 50.488
• IUPAC Standard InChI: InChI=1S/CH3Cl/c1-2/h1H3 Copy

  
• IUPAC Standard InChIKey: NEHMKBQYUWJMIP-UHFFFAOYSA-N Copy
• CAS Registry Number: 74-87-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: Methane, chloro-; Methyl chloride; Artic; Freon 40; Monochloromethane; CH3Cl; Chloor-methaan; Chlor-methan; Chlorure de methyle; Clorometano; Cloruro di metile; Methylchlorid; Metylu chlorek; R 40; Rcra waste number U045; UN 1063; Refrigerant R40
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Reaction thermochemistry data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Henry's Law data
  • Gas phase ion energetics data
  • Ion clustering data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Vibrational and/or electronic energy levels
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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Reaction thermochemistry data

Go To: Top, 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

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

 +  = ( • )

By formula: Cl^- + CH₃Cl = (Cl^- • CH₃Cl)

CH₂Cl^- +  =

By formula: CH₂Cl^- + H⁺ = CH₃Cl

(CH₂Cl⁺ • ) +  = (CH₂Cl⁺ • 2)

By formula: (CH₂Cl⁺ • CH₃Cl) + CH₃Cl = (CH₂Cl⁺ • 2CH₃Cl)

Free energy of reaction

(CH₄Cl⁺ • ) +  = (CH₄Cl⁺ • 2)

By formula: (CH₄Cl⁺ • CH₃Cl) + CH₃Cl = (CH₄Cl⁺ • 2CH₃Cl)

Free energy of reaction

CH₂Cl⁺ +  = (CH₂Cl⁺ • )

By formula: CH₂Cl⁺ + CH₃Cl = (CH₂Cl⁺ • CH₃Cl)

Free energy of reaction

C₃H₇⁺ +  = (C₃H₇⁺ • )

By formula: C₃H₇⁺ + CH₃Cl = (C₃H₇⁺ • CH₃Cl)

 +  = ( • )

By formula: CH₃⁺ + CH₃Cl = (CH₃⁺ • CH₃Cl)

 +  = ( • )

By formula: Br^- + CH₃Cl = (Br^- • CH₃Cl)

CN^- +  = (CN^- • )

By formula: CN^- + CH₃Cl = (CN^- • CH₃Cl)

CH₃Cl₂^- + 2 = C₂H₆Cl₃^-

By formula: CH₃Cl₂^- + 2CH₃Cl = C₂H₆Cl₃^-

C₂H₆Cl₃^- + 3 = C₃H₉Cl₄^-

By formula: C₂H₆Cl₃^- + 3CH₃Cl = C₃H₉Cl₄^-

C₃H₉Cl₄^- + 4 = C₄H₁₂Cl₅^-

By formula: C₃H₉Cl₄^- + 4CH₃Cl = C₄H₁₂Cl₅^-

C₄H₁₂Cl₅^- + 5 = C₅H₁₅Cl₆^-

By formula: C₄H₁₂Cl₅^- + 5CH₃Cl = C₅H₁₅Cl₆^-

C₅H₁₅Cl₆^- + 6 = C₆H₁₈Cl₇^-

By formula: C₅H₁₅Cl₆^- + 6CH₃Cl = C₆H₁₈Cl₇^-

C₆H₁₈Cl₇^- + 7 = C₇H₂₁Cl₈^-

By formula: C₆H₁₈Cl₇^- + 7CH₃Cl = C₇H₂₁Cl₈^-

C₇H₂₁Cl₈^- + 8 = C₈H₂₄Cl₉^-

By formula: C₇H₂₁Cl₈^- + 8CH₃Cl = C₈H₂₄Cl₉^-

C₂H₅⁺ +  = (C₂H₅⁺ • )

By formula: C₂H₅⁺ + CH₃Cl = (C₂H₅⁺ • CH₃Cl)

 +  = ( • )

By formula: Li⁺ + CH₃Cl = (Li⁺ • CH₃Cl)

C₄H₉⁺ +  = (C₄H₉⁺ • )

By formula: C₄H₉⁺ + CH₃Cl = (C₄H₉⁺ • CH₃Cl)

CH₆N⁺ +  = (CH₆N⁺ • )

By formula: CH₆N⁺ + CH₃Cl = (CH₆N⁺ • CH₃Cl)

 +  =  + 

By formula: H₂ + CH₃Cl = CH₄ + HCl

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]

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]

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]

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]

Yamdagni and Kebarle, 1971
Yamdagni, R.; Kebarle, P., Hydrogen bonding energies to negative ions from gas phase measurements of ionic equilibria, J. Am. Chem. Soc., 1971, 93, 7139. [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]

French, Ikuta, et al., 1982
French, M.A.; Ikuta, S.; Kebarle, P., Hydrogen bonding of O-H and C-H hydrogen donors to Cl^-. Results from mass spectrometric measurement of the ion-molecule equilibria RH + Cl^- = RHCl^-, Can. J. Chem., 1982, 60, 1907. [all data]

Hierl, Henchman, et al., 1992
Hierl, P.M.; Henchman, M.J.; Paulson, J.F., Threshold Energies for the Reactions HO- + MeX - MeOH + X- measured by Tandem Mass Spectrometry: Acidities of MeCl and MeBr, Int. J. Mass Spectrom. Ion Proc., 1992, 117, 475, https://doi.org/10.1016/0168-1176(92)80109-E . [all data]

Ingemann and Nibbering, 1985
Ingemann, S.; Nibbering, N.M.M., Gas-phase acidity of CH₃X [X = P(CH₃)₂, SCH₃, F, Cl, Br, I] compounds, J. Chem. Soc. Perkin Trans. 2, 1985, 837. [all data]

Rogers, Simpson, et al., 2010
Rogers, N.J.; Simpson, M.J.; Tuckett, R.P.; Dunn, K.F.; Latimer, C.J., Vacuum-UV negative photoion spectroscopy of CH3F, CH3Cl and CH3Br, Phys. Chem. Chem. Phys., 2010, 12, 36, 10971-10980, https://doi.org/10.1039/c0cp00234h . [all data]

Poutsma, Nash, et al., 1997
Poutsma, J.C.; Nash, J.J.; Paulino, J.A.; Squires, R.R., Absolute Heats of Formation of Phenylcarbene and Vinylcarbene, J. Am. Chem. Soc., 1997, 119, 20, 4686, https://doi.org/10.1021/ja963918s . [all data]

Henchman, Hierl, et al., 1985
Henchman, M.; Hierl, P.M.; Paulson, J.F., Nucleophilic displacement vs. proton tranfer: The system OH-.(H₂O)_0,1,2 + CH₃Cl in the relative energy range 0.03-5 eV, J. Am. Chem. Soc., 1985, 107, 2812. [all data]

Luczynski, Malicki, et al., 1974
Luczynski, Z.; Malicki, W.; Wincel, H., Positive Ion Reactions of Methyl Cloride in the Gas Phase, Int. J. Mass Spectrom. Ion Phys., 1974, 15, 3, 321, https://doi.org/10.1016/0020-7381(74)85009-6 . [all data]

Sen Sharma and Kebarle, 1978
Sen Sharma, D.K.; Kebarle, P., Binding Energies and Stabilities of Chloronium Ions from Study of the Gas - Phase Equilibria: R1+ + ClR2 = R1ClR2+, J. Am. Chem. Soc., 1978, 100, 18, 5826, https://doi.org/10.1021/ja00486a039 . [all data]

McMahon, Heinis, et al., 1988
McMahon, T.; Heinis, T.; Nicol, G.; Hovey, J.K.; Kebarle, P., Methyl Cation Affinities, J. Am. Chem. Soc., 1988, 110, 23, 7591, https://doi.org/10.1021/ja00231a002 . [all data]

Foster, Williamson, et al., 1974
Foster, M.S.; Williamson, A.D.; Beauchamp, J.L., Photoionization mass spectrometry of trans-azomethane, Int. J. Mass Spectrom. Ion Phys., 1974, 15, 429. [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]

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]

Meot-Ner, 1984
Meot-Ner, (Mautner)M., The Ionic Hydrogen Bond and Ion Solvation. 1. -NH+ O-, -NH+ N- and -OH+ O- Bonds. Correlations with Proton Affinity. Deviations Due to Structural Effects, J. Am. Chem. Soc., 1984, 106, 5, 1257, https://doi.org/10.1021/ja00317a015 . [all data]

Lacher, Emery, et al., 1956
Lacher, J.R.; Emery, E.; Bohmfalk, E.; Park, J.D., Reaction heats of organic compounds. IV. A high temperature calorimeter and the hydrogenation of methyl ethyl and vinyl chlorides, J. Phys. Chem., 1956, 60, 492-495. [all data]

Notes

Go To: Top, Reaction thermochemistry data, References

• Symbols used in this document:
  

  T	Temperature
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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