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:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry 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
  • References
  • Notes
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
  • X-ray Photoelectron Spectroscopy Database, version 5.0
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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

Gas Phase Heat Capacity (Shomate Equation)

C_p° = 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
    C_p = heat capacity (J/mol*K)
    H° = standard enthalpy (kJ/mol)
    S° = standard entropy (J/mol*K)
    t = temperature (K) / 1000.

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Condensed 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.
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of liquid

Phase change 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:
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
DRB - Donald R. Burgess, Jr.
DH - Eugene S. Domalski and Elizabeth D. Hearing
AC - William E. Acree, Jr., James S. Chickos
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein

Enthalpy of vaporization

Entropy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

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

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

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)

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

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:
HL - Edward P. Hunter and Sharon G. Lias
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

View reactions leading to CH₃Cl⁺ (ion structure unspecified)

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

CH₂Cl^- +  =

By formula: CH₂Cl^- + H⁺ = CH₃Cl

Ion clustering 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

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. Searches may be limited to ion clustering reactions. A general reaction search form is also available.

Clustering reactions

 +  = ( • )

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

CH₂Cl⁺ +  = (CH₂Cl⁺ • )

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

Free energy of reaction

(CH₂Cl⁺ • ) +  = (CH₂Cl⁺ • 2)

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

Free energy of reaction

 +  = ( • )

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

CH₃Cl₂^- + 2 = C₂H₆Cl₃^-

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

(CH₄Cl⁺ • ) +  = (CH₄Cl⁺ • 2)

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

Free energy of reaction

CH₆N⁺ +  = (CH₆N⁺ • )

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

CN^- +  = (CN^- • )

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

C₂H₅⁺ +  = (C₂H₅⁺ • )

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

C₂H₆Cl₃^- + 3 = C₃H₉Cl₄^-

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

C₃H₇⁺ +  = (C₃H₇⁺ • )

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

C₃H₉Cl₄^- + 4 = C₄H₁₂Cl₅^-

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

C₄H₉⁺ +  = (C₄H₉⁺ • )

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

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^-

 +  = ( • )

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

 +  = ( • )

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

IR Spectrum

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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: Coblentz Society, Inc.

Gas Phase Spectrum

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Notice: Except where noted, spectra from this collection were measured on dispersive instruments, often in carefully selected solvents, and hence may differ in detail from measurements on FTIR instruments or in other chemical environments. More information on the manner in which spectra in this collection were collected can be found here.

Notice: Concentration information is not available for this spectrum and, therefore, molar absorptivity values cannot be derived.

Additional Data

Mass spectrum (electron ionization)

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Vibrational and/or electronic energy levels

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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: Takehiko Shimanouchi

Symmetry:   C_3ν     Symmetry Number σ = 3

Source: Shimanouchi, 1972

Notes

Gas Chromatography

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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: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry 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, 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]

Fletcher and Pilcher, 1971
Fletcher, R.A.; Pilcher, G., Measurements of heats of combustion by flame calorimetry. Part 7.?Chloromethane, chloroethane, 1-chloropropane, 2-chloropropane, Trans. Faraday Soc., 1971, 67, 3191, https://doi.org/10.1039/tf9716703191 . [all data]

Fletcher and Pilcher, 1971, 2
Fletcher, R.A.; Pilcher, G., Measurements of heats of combustion by flame calorimetry. Part 7.-Chloromethane, chloroethane, 1-chloropropane, 2-chloropropane, Trans. Faraday Soc., 1971, 67, 3191-3201. [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]

Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G., Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [all data]

Messerly and Aston, 1940
Messerly, G.H.; Aston, J.G., The heat capacity and entropy, heats of fusion and vaporization and the vapor pressure of methyl chloride, J. Am. Chem. Soc., 1940, 62, 886-890. [all data]

Awberg and Griffiths, 1940
Awberg, J.H.; Griffiths, E., The specific heat of liquid methyl chloride, Proc. Phys. Soc. (London), 1940, 52, 770-776. [all data]

Shorthose, 1924
Shorthose, D.N., G. B. DSIR, Food Invest. Board, Spec. Rept., 1924, No. 19, 16pp. [all data]

Awbery, 1941
Awbery, J.H., Philos. Mag., 1941, 31, 247. [all data]

Timmermans, 1921
Timmermans, J., The Freezing Points of Organic Substances IV. New Exp. Determinations, Bull. Soc. Chim. Belg., 1921, 30, 62. [all data]

Timmermans, 1911
Timmermans, J., Researches on the freezing point of organic liquid compounds, Bull. Soc. Chim. Belg., 1911, 25, 300. [all data]

Messerly and Aston, 1940, 2
Messerly, G.H.; Aston, J.G., The Heat Capacity and Entropy, Heats of Fusion and Vaporization and the Vapor Pressure of Methyl Chloride, J. Am. Chem. Soc., 1940, 62, 886-90. [all data]

Mansoorian, Hall, et al., 1981
Mansoorian, H.; Hall, K.R.; Holste, J.C.; Eubank, P.T., The density of gaseous ethane and of fluid methyl chloride and the vapor pressure of methyl chloride, J. Chem. Thermodyn., 1981, 13, 1001-24. [all data]

Hsu and McKetta, 1964
Hsu, C.C.; McKetta, J.J., Pressure-Volume-Temperature Properties of Methyl Chloride, J. Chem. Eng. Data, 1964, 9, 1, 45-51, https://doi.org/10.1021/je60020a014 . [all data]

Leduc, 1909
Leduc, A., Compressibility of gases between 0 atm and 3 atm and at all temperatures, C. R. Hebd. Seances Acad. Sci., 1909, 148, 407. [all data]

Vincent and Chappuis, 1886
Vincent, C.; Chappuis, J., J. Phys. Theor. Appl., 1886, 5, 58. [all data]

Centnerszwer, 1904
Centnerszwer, M., An Application of the Method of Cailletet and Mathias to Determine Critical Volume., Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1904, 49, 199. [all data]

Beersmans and Jungers, 2010
Beersmans, J.; Jungers, J.C., Synthèse et Étude des Chlorure, Bromure et Iodure de Deutérométhyle, Bull. Soc. Chim. Belges, 2010, 56, 5-8, 238-250, https://doi.org/10.1002/bscb.19470560506 . [all data]

Ganeff and Jungers, 2010
Ganeff, Jean M.; Jungers, Joseph C., Tensions de vapeur du système CH3Cl «63743» CH2Cl2, Bull. Soc. Chim. Belges, 2010, 57, 1-3, 82-87, https://doi.org/10.1002/bscb.19480570109 . [all data]

Stephenson and Malanowski, 1987
Stephenson, Richard M.; Malanowski, Stanislaw, Handbook of the Thermodynamics of Organic Compounds, 1987, https://doi.org/10.1007/978-94-009-3173-2 . [all data]

Thomson, 1946
Thomson, George Wm., The Antoine Equation for Vapor-pressure Data., Chem. Rev., 1946, 38, 1, 1-39, https://doi.org/10.1021/cr60119a001 . [all data]

Yates, 1926
Yates, G.W.C., LXXIV. Latent heats of vaporization of ethyl and methyl chlorides, Philos. Mag., 1926, 2, 817-826. [all data]

Ganeff and Jungers, 1948
Ganeff, J.M.; Jungers, J.C., Tensions de Vapeur du Systeme CH3Cl - CH2Cl2, Bull. Soc. Chim. Belg., 1948, 57, 1-3, 82-87, https://doi.org/10.1002/bscb.19480570109 . [all data]

Beersmans and Jungers, 1947
Beersmans, J.; Jungers, J.C., Synthese et Etude des Chlorure, Bromure et Iodure de Deuteromethyle, Bull. Soc. Chim. Belg., 1947, 56, 5-8, 238-250, https://doi.org/10.1002/bscb.19470560506 . [all data]

Bah and Dupont-Pavlovsky, 1995
Bah, A.; Dupont-Pavlovsky, N., Vapor Pressure of Solid Chloromethane, J. Chem. Eng. Data, 1995, 40, 4, 869-870, https://doi.org/10.1021/je00020a028 . [all data]

Domalski and Hearing, 1996
Domalski, Eugene S.; Hearing, Elizabeth D., Heat Capacities and Entropies of Organic Compounds in the Condensed Phase. Volume III, J. Phys. Chem. Ref. Data, 1996, 25, 1, 1, https://doi.org/10.1063/1.555985 . [all data]

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]

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]

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]

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Hochmann, Templet, et al., 1975
Hochmann, P.; Templet, P.H.; Wang, H.-t.; McGlynn, S.P., Molecular Rydberg transitions. I. Low-energy Rydberg transitions in methyl halides, J. Chem. Phys., 1975, 62, 2588. [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]

Ragle, Stenhouse, et al., 1970
Ragle, J.L.; Stenhouse, I.A.; Frost, D.C.; McDowell, C.A., Valence-shell ionization potentials of halomethanes by photoelectron spectroscopy. I. CH₃Cl, CH₃Br, CH₃I. Vibrational frequencies and vibronic interaction in CH₃Br⁺ and CH₃Cl⁺, J. Chem. Phys., 1970, 53, 178. [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]

Nicholson, 1965
Nicholson, A.J.C., Photoionization-efficiency curves. II. False and genuine structure, J. Chem. Phys., 1965, 43, 1171. [all data]

Dibeler and Walker, 1965
Dibeler, V.H.; Walker, J.A., Ion-pair process in CH₃Cl by photoionization, J. Chem. Phys., 1965, 43, 1842. [all data]

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

Price, 1936
Price, W.C., The far ultraviolet absorption spectra and ionization potentials of the alkyl halides. Part I, J. Chem. Phys., 1936, 4, 539. [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]

Utsunomiya, Kobayashi, et al., 1980
Utsunomiya, C.; Kobayashi, T.; Nagakura, S., Photoelectron angular distribution measurements for some aliphatic alcohols, amines, halides, Bull. Chem. Soc. Jpn., 1980, 53, 1216. [all data]

Uehara, Saito, et al., 1973
Uehara, Y.; Saito, N.; Yonezawa, T., Ionization potentials of trifluoromethyl and methyl halides by photoelectron spectroscopy and calculations by extended Hucket and CNDO/2 methods, Chem. Lett., 1973, 495. [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]

Tsuda and Hamill, 1964
Tsuda, S.; Hamill, W.H., Structure in ionization efficiency curves near threshold from alkanes and alkyl halides, J. Chem. Phys., 1964, 41, 2713. [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]

Krauss, Walker, et al., 1968
Krauss, M.; Walker, J.A.; Dibeler, V.H., Mass spectrometric study of photoionization. X. Hydrogen chloride and methyl halides, J. Res. NBS, 1968, 72A, 281. [all data]

Tsuda, Melton, et al., 1964
Tsuda, S.; Melton, C.E.; Hamill, W.H., Ionization- efficiency curves for molecular and fragment ions from methane and the methyl halides, J. Chem. Phys., 1964, 41, 689. [all data]

Shimanouchi, 1972
Shimanouchi, T., Tables of Molecular Vibrational Frequencies Consolidated Volume I, National Bureau of Standards, 1972, 1-160. [all data]

Pacáková, Vojtechová, et al., 1988
Pacáková, V.; Vojtechová, H.; Coufal, P., Reaction gas chromatography: study of the photodecomposition of halogenated hydrocarbons, Chromatographia, 1988, 25, 7, 621-626, https://doi.org/10.1007/BF02327659 . [all data]

Hively and Hinton, 1968
Hively, R.A.; Hinton, R.E., Variation of the retention index with temperature on squalane substrates, J. Gas Chromatogr., 1968, 6, 4, 203-217, https://doi.org/10.1093/chromsci/6.4.203 . [all data]

White, Douglas, et al., 1992
White, C.M.; Douglas, L.J.; Hackett, J.P.; Anderson, R.R., Characterization of synthetic gasoline from the chloromethane-zeolite reaction, Energy Fuels, 1992, 6, 1, 76-82, https://doi.org/10.1021/ef00031a012 . [all data]

Zenkevich, 2005
Zenkevich, I.G., Experimentally measured retention indices., 2005. [all data]

Zenkevich, Eliseenkov, et al., 2006
Zenkevich, I.G.; Eliseenkov, E.V.; Kasatochkin, A.N., Application of Retention Indices in GC-MS Identification of Halogenated Organic Compounds, Mass Spectromery (Rus.), 2006, 3, 2, 131-140. [all data]

Blunden, Aneja, et al., 2005
Blunden, J.; Aneja, V.P.; Lonneman, W.A., Characterization of non-methane volatile organic compounds at swine facilities in eastern North Carolina, Atm. Environ., 2005, 39, 36, 6707-6718, https://doi.org/10.1016/j.atmosenv.2005.03.053 . [all data]

Zenkevich, 1999
Zenkevich, I.G., Mutual Correlation between Gas-Chromatographic Retention Indices of Organic Compounds from Different Series, Zh. Anal. Khim., 1999, 54, 12, 1272-1279. [all data]

Zenkevich, 1998
Zenkevich, I.G., Reciprocally Unambiguous Conformity Between GC Retention Indices and Boiling Points within Two- and Multidimensional Taxonomic Groups of Organic Compounds, J. Hi. Res. Chromatogr., 1998, 21, 10, 565-568, https://doi.org/10.1002/(SICI)1521-4168(19981001)21:10<565::AID-JHRC565>3.0.CO;2-6 . [all data]

Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A., New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments, Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]

Notes

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

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  Ptriple	Triple point pressure
  S°gas,1 bar	Entropy of gas at standard conditions (1 bar)
  S°liquid	Entropy of liquid at standard conditions
  T	Temperature
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  d(ln(kH))/d(1/T)	Temperature dependence parameter for Henry's Law constant
  k°H	Henry's Law constant at 298.15K
  ΔcH°gas	Enthalpy of combustion of gas at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°liquid	Enthalpy of formation of liquid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔrS°	Entropy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization
  ρc	Critical density

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