Ethyl Chloride

• Formula: C₂H₅Cl
• Molecular weight: 64.514
• IUPAC Standard InChI: InChI=1S/C2H5Cl/c1-2-3/h2H2,1H3 Copy

  
• IUPAC Standard InChIKey: HRYZWHHZPQKTII-UHFFFAOYSA-N Copy
• CAS Registry Number: 75-00-3
• 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: Ethane, chloro-; Aethylis; Aethylis chloridum; Anodynon; Chelen; Chlorene; Chlorethyl; Chloridum; Chloroethane; Chloryl; Chloryl anesthetic; Cloretilo; Dublofix; Ether chloratus; Ether hydrochloric; Ether muriatic; Hydrochloric ether; Kelene; Monochlorethane; Monochloroethane; Muriatic ether; Narcotile; C2H5Cl; Aethylchlorid; Chloorethaan; Chloroaethan; Chlorure D'ethyle; Cloroetano; Cloruro di etile; Etylu chlorek; NCI-C06224; UN 1037; Chloryle anesthetic
• 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
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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

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:
BS - Robert L. Brown and Stephen E. Stein
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 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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
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. 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^- + C₂H₅Cl = (Cl^- • C₂H₅Cl)

=  + 

By formula: C₂H₅Cl = C₂H₄ + HCl

(C₂H₅⁺ • 2) +  = (C₂H₅⁺ • 3)

By formula: (C₂H₅⁺ • 2C₂H₅Cl) + C₂H₅Cl = (C₂H₅⁺ • 3C₂H₅Cl)

(C₂H₅⁺ • ) +  = (C₂H₅⁺ • 2)

By formula: (C₂H₅⁺ • C₂H₅Cl) + C₂H₅Cl = (C₂H₅⁺ • 2C₂H₅Cl)

 +  = ( • )

By formula: Br^- + C₂H₅Cl = (Br^- • C₂H₅Cl)

 +  = ( • )

By formula: CH₃⁺ + C₂H₅Cl = (CH₃⁺ • C₂H₅Cl)

C₄H₉⁺ +  = (C₄H₉⁺ • )

By formula: C₄H₉⁺ + C₂H₅Cl = (C₄H₉⁺ • C₂H₅Cl)

 +  =  + 

By formula: H₂ + C₂H₅Cl = C₂H₆ + 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:
MM - Michael M. Meot-Ner (Mautner)
LL - Sharon G. Lias and Joel F. Liebman
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

View reactions leading to C₂H₅Cl⁺ (ion structure unspecified)

Proton affinity at 298K

Gas basicity at 298K

Protonation entropy at 298K

Ionization energy determinations

Appearance energy determinations

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^- + C₂H₅Cl = (Br^- • C₂H₅Cl)

 +  = ( • )

By formula: CH₃⁺ + C₂H₅Cl = (CH₃⁺ • C₂H₅Cl)

(C₂H₅⁺ • ) +  = (C₂H₅⁺ • 2)

By formula: (C₂H₅⁺ • C₂H₅Cl) + C₂H₅Cl = (C₂H₅⁺ • 2C₂H₅Cl)

(C₂H₅⁺ • 2) +  = (C₂H₅⁺ • 3)

By formula: (C₂H₅⁺ • 2C₂H₅Cl) + C₂H₅Cl = (C₂H₅⁺ • 3C₂H₅Cl)

C₄H₉⁺ +  = (C₄H₉⁺ • )

By formula: C₄H₉⁺ + C₂H₅Cl = (C₄H₉⁺ • C₂H₅Cl)

 +  = ( • )

By formula: Cl^- + C₂H₅Cl = (Cl^- • C₂H₅Cl)

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• GAS (100 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm^-1 resolution

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

• gas

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_s     Symmetry Number σ = 1

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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Kovats' RI, 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, isothermal

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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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Normal alkane RI, 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, NIST Free Links, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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, 3191-3201. [all data]

Casey and Fordham, 1951
Casey, D.W.H.; Fordham, S., An all-glass calorimeter, and the heat of combustion of ethyl chloride, J. Chem. Soc., 1951, 2513-2516. [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]

Gordon and Giauque, 1948
Gordon, J.; Giauque, W.F., The entropy of ethyl chloride. Heat capacity from 18 to 287K. Vapor pressure. Heats of fusion and vaporization, J. Am. Chem. Soc., 1948, 70, 1506-1510. [all data]

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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]

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Gordon, J.; Giauque, W.F., The Entropy of Ethyl Chloride. Heat Capacity from 13 to 287 K. Vapor Pressure. Heats of Fusion and Vaporization, J. Am. Chem. Soc., 1948, 70, 1506. [all data]

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Berthoud, A., Determination of Critical Temperatures and Pressures of Amines and Alkyl Chlorides, J. Chim. Phys. Phys.-Chim. Biol., 1917, 15, 3. [all data]

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Li, J.C.M.; Rossini, F.D., Vapor Pressures and Boiling Points of the l-Fluoroalkanes, l-Chloroalkanes, l-Bromoalkanes, and l-Iodoalkanes, C ₁ to C ₂₀ ., J. Chem. Eng. Data, 1961, 6, 2, 268-270, https://doi.org/10.1021/je60010a025 . [all data]

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Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

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Larson, J.W.; McMahon, T.B., Fluoride and chloride affinities of main group oxides, fluorides, oxofluorides, and alkyls. Quantitative scales of lewis acidities from ion cyclotron resonance halide-exchange equilibria, J. Phys. Chem., 1984, 88, 1083. [all data]

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Luczynski and Wincel, 1974
Luczynski, Z.; Wincel, H., Ion - Molecule Reactions in Ethyl Chloride, Int. J. Mass Spectrom. Ion Phys., 1974, 14, 1, 29, https://doi.org/10.1016/0020-7381(74)80059-8 . [all data]

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Rosenstock, Buff, et al., 1982
Rosenstock, H.M.; Buff, R.; Ferreira, M.A.A.; Lias, S.G.; Parr, A.C.; Stockbauer, R.L.; Holmes, J.L., Fragmentation mechanism and energetics of some alkyl halide ions, J. Am. Chem. Soc., 1982, 104, 2337. [all data]

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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]

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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]

Bouchoux, Caunan, et al., 2001
Bouchoux, G.; Caunan, F.; Leblanc, D.; Nguyen, M.T.; Salpin, J.Y., Protonation thermochemistry of ethyl halides, Chem Phys. Phys. Chem., 2001, 10, 604-610. [all data]

Luo and Pacey, 1992
Luo, Y.-R.; Pacey, P.D., Effects of alkyl substitution on ionization energies of alkanes and haloalkanes and on heats of formation of their molecular cations. Part 2. Alkanes and chloro-, bromo- and iodoalkanes, Int. J. Mass Spectrom. Ion Processes, 1992, 112, 63. [all data]

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Katsumata, S.; Kimura, K., Photoelectron spectra and sum rule consideration. Effect of chlorine substitution on ionization energies for chloroethanes, chloroacetaldehydes and chloroacetyl chlorides, J. Electron Spectrosc. Relat. Phenom., 1975, 6, 309. [all data]

Kimura, Katsumata, et al., 1973
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Irsa, A.P., Electron impact studies on C₂H₅Cl, C₂H₅Br, and C₂H₅I, J. Chem. Phys., 1957, 26, 18. [all data]

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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]

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White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S., Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane, J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211 . [all data]

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Huang, Liang, et al., 1996
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Dimov and Milina, 1989
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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]

Flanagan, Streete, et al., 1997
Flanagan, R.J.; Streete, P.J.; Ramsey, J.D., Volatile Substance Abuse, UNODC Technical Series, No 5, United Nations, Office on Drugs and Crime, Vienna International Centre, PO Box 500, A-1400 Vienna, Austria, 1997, 56, retrieved from http://www.odccp.org/pdf/technical_series₁997-01-01₁.pdf. [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]

Strete, Ruprah, et al., 1992
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Ramsey, J.D.; Flanagan, R.J., Detection and Identification of Volatile Organic Compounds in Blood by Headspace Gas Chromatography as an Aid to the Diagnosis of Solvent Abuse, J. Chromatogr., 1982, 240, 2, 423-444, https://doi.org/10.1016/S0021-9673(00)99622-5 . [all data]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Cp,liquid	Constant pressure heat capacity of liquid
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  S°liquid	Entropy of liquid at standard conditions
  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
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions
  ΔvapS	Entropy of vaporization

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