Ethyl bromide

• Formula: C₂H₅Br
• Molecular weight: 108.965
• IUPAC Standard InChI: InChI=1S/C2H5Br/c1-2-3/h2H2,1H3 Copy

  
• IUPAC Standard InChIKey: RDHPKYGYEGBMSE-UHFFFAOYSA-N Copy
• CAS Registry Number: 74-96-4
• 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, bromo-; Bromic ether; Bromoethane; Hydrobromic ether; Monobromoethane; C2H5Br; 1-Bromoethane; Bromure d'ethyle; Etylu bromek; Halon 2001; NCI-C55481; UN 1891; NSC 8824
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• Information on this page:
  • Phase change data
  • Gas phase ion energetics data
  • Ion clustering data
  • Vibrational and/or electronic energy levels
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Reaction thermochemistry data
  • Henry's Law data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
AC - William E. Acree, Jr., James S. Chickos

Enthalpy of vaporization

Enthalpy of vaporization

Δ_vapH = A exp(-βT_r) (1 − T_r)^β
    Δ_vapH = Enthalpy of vaporization (at saturation pressure) (kJ/mol)
    T_r = reduced temperature (T / T_c)

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Antoine Equation Parameters

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

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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 C₂H₅Br⁺ (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^- + C₂H₅Br = (Br^- • C₂H₅Br)

 +  = ( • )

By formula: Cl^- + C₂H₅Br = (Cl^- • C₂H₅Br)

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

References

Go To: Top, Phase change data, Gas phase ion energetics data, Ion clustering data, Vibrational and/or electronic energy levels, Notes

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

Majer and Svoboda, 1985
Majer, V.; Svoboda, V., Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford, 1985, 300. [all data]

Herz and Neukirch, 1923
Herz, W.; Neukirch, E., On Knowldge of the Critical State, Z. Phys. Chem., Stoechiom. Verwandtschaftsl., 1923, 104, 433-50. [all data]

Lane, Linnett, et al., 1953
Lane, M.R.; Linnett, J.W.; Oswin, H.G., A study of the C₂H₄+HCl=C₂H₅Cl and C2H4+Hbr=C2H5Br equilibria, Proc. Roy. Soc. London A, 1953, 216, 361-374. [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]

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]

Li and Rossini, 1961
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]

Dykyj, 1970
Dykyj, J., Petrochemica, 1970, 10, 2, 51. [all data]

Svoboda, Majer, et al., 1977
Svoboda, V.; Majer, V.; Veselý, F.; Pick, J., Heats of vaporization of alkyl bromides, Collect. Czech. Chem. Commun., 1977, 42, 6, 1755-1760, https://doi.org/10.1135/cccc19771755 . [all data]

Zmaczynski, 1930
Zmaczynski, M.A., J. Chim. Phys. Phys.-Chim. Biol., 1930, 27, 503. [all data]

Boublik, Fried, et al., 1984
Boublik, T.; Fried, V.; Hala, E., The Vapour Pressures of Pure Substances: Selected Values of the Temperature Dependence of the Vapour Pressures of Some Pure Substances in the Normal and Low Pressure Region, 2nd ed., Elsevier, New York, 1984, 972. [all data]

Zmaczynski, 1930, 2
Zmaczynski, M.A., Recherches Ebullioscopiques et Tonometriques Comparatives de 8 Substances Organiques Etalons, J. Chim. Phys. Phys. Chim. Biol., 1930, 27, 503-517. [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]

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]

Ohno, Imai, et al., 1985
Ohno, K.; Imai, K.; Harada, Y., Variations in reactivity of lone-pair electrons due to intramolecular hydrogen bonding as observed by penning ionization electron spectroscopy, J. Am. Chem. Soc., 1985, 107, 8078. [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]

Johnstone, Mellon, et al., 1970
Johnstone, R.A.W.; Mellon, F.A.; Ward, S.D., Online acquisition of ionization efficiency data, Intern. J. Mass Spectrom. Ion Phys., 1970, 5, 241. [all data]

Hashmall and Heilbronner, 1970
Hashmall, J.A.; Heilbronner, E., n-Ionization potentials of alkyl bromides, Angew. Chem. Intern. Ed., 1970, 9, 305. [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 II, J. Chem. Phys., 1936, 4, 547. [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]

Hoppilliard and Solgadi, 1980
Hoppilliard, Y.; Solgadi, D., Conformational analysis of 2-haloethanols and 2-methoxyethylhalides in a photoelectron spectrometer, Tetrahedron, 1980, 36, 377. [all data]

Kimura, Katsumata, et al., 1973
Kimura, K.; Katsumata, S.; Achiba, Y.; Matsumoto, H.; Nagakura, S., Photoelectron spectra and orbital structures of higher alkyl chlorides, bromides, and iodides., Bull. Chem. Soc. Jpn., 1973, 46, 373. [all data]

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

Miller and Baer, 1984
Miller, B.E.; Baer, T., Kinetic energy release distribution in the fragmentation of energy-selected vinyl and ethyl bromide ions, Chem. Phys., 1984, 85, 39. [all data]

Traeger and McLoughlin, 1981
Traeger, J.C.; McLoughlin, R.G., Absolute heats of formation for gas phase cations, J. Am. Chem. Soc., 1981, 103, 3647. [all data]

Johnstone and Mellon, 1972
Johnstone, R.A.W.; Mellon, F.A., Electron-impact ionization and appearance potentials, J. Chem. Soc. Faraday Trans. 2, 1972, 68, 1209. [all data]

Grutzmacher, 1970
Grutzmacher, H.-F., Zum Mechanismus massenspektrometrischer Fragmentierungsreaktionen-IV: zur Bildung von Phenonium-Ionen bei der Elektronenstoss-Fragmentierung von -Phenylathylbromiden, Org. Mass Spectrom., 1970, 3, 131. [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]

Dougherty, 1974
Dougherty, R.C., SN₂ reactions in the gas phase. Alkyl group structural effects, Org. Mass Spectrom., 1974, 8, 85. [all data]

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

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  IE (evaluated)	Recommended ionization energy
  Pc	Critical pressure
  Tboil	Boiling point
  Tc	Critical temperature
  Tfus	Fusion (melting) point
  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
  ρc	Critical density

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