Ethyl bromide
- Formula: C2H5Br
- Molecular weight: 108.965
- IUPAC Standard InChIKey: RDHPKYGYEGBMSE-UHFFFAOYSA-N
- 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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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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | -63.6 | kJ/mol | Cm | Kudchadker and Kudchadker, 1979 | |
ΔfH°gas | -65.3 ± 6.3 | kJ/mol | Chyd | Ashcroft, Carson, et al., 1965 | |
ΔfH°gas | -61.9 ± 1.0 | kJ/mol | Chyd | Fowell, Lacher, et al., 1965 | |
ΔfH°gas | -64.6 ± 2.1 | kJ/mol | Eqk | Lane, Linnett, et al., 1953 |
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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | -95.5 ± 2.1 | kJ/mol | Chyd | Ashcroft, Carson, et al., 1965 | Reanalyzed by Pedley, Naylor, et al., 1986, Original value = -96.2 ± 6.3 kJ/mol; ALS |
Constant pressure heat capacity of liquid
Cp,liquid (J/mol*K) | Temperature (K) | Reference | Comment |
---|---|---|---|
105.8 | 298.15 | Shehatta, 1993 | DH |
100.8 | 298. | Kurbatov, 1948 | T = -50 to 37°C; mean Cp, five temperatures.; DH |
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
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
Tboil | 311.5 ± 0.4 | K | AVG | N/A | Average of 15 out of 16 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 155. ± 2. | K | AVG | N/A | Average of 6 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 503.8 | K | N/A | Majer and Svoboda, 1985 | |
Tc | 503.95 | K | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.4 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Pc | 62.3149 | bar | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.8106 bar; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ρc | 4.65 | mol/l | N/A | Herz and Neukirch, 1923 | Uncertainty assigned by TRC = 0.03 mol/l; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 28.26 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 28. ± 1. | kJ/mol | V | Lane, Linnett, et al., 1953 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
27.04 | 311.6 | N/A | Majer and Svoboda, 1985 | |
26.9 | 349. | A | Stephenson and Malanowski, 1987 | Based on data from 334. to 504. K.; AC |
26.6 | 341. | A | Stephenson and Malanowski, 1987 | Based on data from 326. to 454. K.; AC |
31.0 | 467. | A | Stephenson and Malanowski, 1987 | Based on data from 452. to 503. K.; AC |
30.6 | 240. | E | Stephenson and Malanowski, 1987 | Based on data from 225. to 333. K. See also Li and Rossini, 1961 and Dykyj, 1970.; AC |
27.6 ± 0.1 | 305. | C | Svoboda, Majer, et al., 1977 | AC |
27.0 ± 0.1 | 312. | C | Svoboda, Majer, et al., 1977 | AC |
26.2 ± 0.1 | 323. | C | Svoboda, Majer, et al., 1977 | AC |
27.9 | 316. | N/A | Zmaczynski, 1930 | Based on data from 301. to 348. K. See also Boublik, Fried, et al., 1984.; AC |
Enthalpy of vaporization
ΔvapH =
A exp(-βTr) (1 − Tr)β
ΔvapH =
Enthalpy of vaporization (at saturation pressure)
(kJ/mol)
Tr = reduced temperature (T / Tc)
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Temperature (K) | A (kJ/mol) | β | Tc (K) | Reference | Comment |
---|---|---|---|---|---|
305. to 323. | 49.38 | 0.3807 | 503.8 | Majer and Svoboda, 1985 |
Antoine Equation Parameters
log10(P) = A − (B / (T + C))
P = vapor pressure (bar)
T = temperature (K)
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Temperature (K) | A | B | C | Reference | Comment |
---|---|---|---|---|---|
301.29 to 348.51 | 4.11241 | 1121.371 | -38.478 | Zmaczynski, 1930, 2 | Coefficents calculated by NIST from author's data. |
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) = k°H exp(d(ln(kH))/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(kH))/d(1/T) = Temperature dependence constant (K)
k°H (mol/(kg*bar)) | d(ln(kH))/d(1/T) (K) | Method | Reference | Comment |
---|---|---|---|---|
0.13 | Q | N/A | missing citation give several references for the Henry's law constants but don't assign them to specific species. | |
0.13 | V | N/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:
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
IE (evaluated) | 10.29 ± 0.01 | eV | N/A | N/A | L |
Quantity | Value | Units | Method | Reference | Comment |
Proton affinity (review) | 696.2 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Quantity | Value | Units | Method | Reference | Comment |
Gas basicity | 669.7 | kJ/mol | N/A | Hunter and Lias, 1998 | HL |
Proton affinity at 298K
Proton affinity (kJ/mol) | Reference | Comment |
---|---|---|
684.3 ± 1.6 | Bouchoux, Caunan, et al., 2001 | T = 300K; MM |
Gas basicity at 298K
Gas basicity (review) (kJ/mol) | Reference | Comment |
---|---|---|
660.5 ± 1.6 | Bouchoux, Caunan, et al., 2001 | T = 300K; MM |
Protonation entropy at 298K
Protonation entropy (J/mol*K) | Reference | Comment |
---|---|---|
29.2 | Bouchoux, Caunan, et al., 2001 | T = 300K; MM |
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
10.31 | EST | Luo and Pacey, 1992 | LL |
10.2 | PE | Ohno, Imai, et al., 1985 | LBLHLM |
10.30 | PE | Kimura, Katsumata, et al., 1981 | LLK |
10.24 ± 0.03 | EI | Johnstone, Mellon, et al., 1970 | RDSH |
10.30 ± 0.015 | PE | Hashmall and Heilbronner, 1970 | RDSH |
10.29 ± 0.01 | PI | Watanabe, 1957 | RDSH |
10.29 ± 0.02 | S | Price, 1936 | RDSH |
10.30 | PE | Ohno, Imai, et al., 1985 | Vertical value; LBLHLM |
10.30 | PE | Kimura, Katsumata, et al., 1981 | Vertical value; LLK |
10.29 | PE | Utsunomiya, Kobayashi, et al., 1980 | Vertical value; LLK |
10.28 | PE | Hoppilliard and Solgadi, 1980 | Vertical value; LLK |
10.28 | PE | Kimura, Katsumata, et al., 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
Br+ | 18.6 ± 0.3 | ? | EI | Irsa, 1957 | RDSH |
CH2Br+ | 14.1 ± 0.1 | CH3 | EI | Irsa, 1957 | RDSH |
CH3+ | 16.9 ± 0.3 | ? | EI | Irsa, 1957 | RDSH |
C2H5+ | 11.21 ± 0.05 | Br | PIPECO | Miller and Baer, 1984 | T = 0K; LBLHLM |
C2H5+ | 11.05 ± 0.01 | Br | PI | Traeger and McLoughlin, 1981 | T = 298K; LLK |
C2H5+ | 11.14 | Br | PI | Traeger and McLoughlin, 1981 | T = 0K; LLK |
C2H5+ | 10.72 ± 0.08 | Br | EI | Johnstone and Mellon, 1972 | LLK |
C2H5+ | 11.15 | Br | EI | Grutzmacher, 1970 | RDSH |
References
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Kudchadker and Kudchadker, 1979
Kudchadker, S.A.; Kudchadker, A.P.,
Ideal gas thermodynamic properties of selected bromoethanes and iodoethane,
J. Phys. Chem. Ref. Data, 1979, 8, 519-526. [all data]
Ashcroft, Carson, et al., 1965
Ashcroft, S.J.; Carson, A.S.; Carter, W.; Laye, P.G.,
Thermochemistry of reductions caused by lithium aluminium hydride. Part 3.- The C-halogen bond dissociation energies in ethyl iodine and ethyl bromide,
Trans. Faraday Soc., 1965, 61, 225-229. [all data]
Fowell, Lacher, et al., 1965
Fowell, P.; Lacher, J.R.; Park, J.D.,
Reaction heats of organic compounds. Part 3.-Heats of hydrogenation of methyl bromide and ethyl bromide,
Trans. Faraday Soc., 1965, 61, 1324-1327. [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]
Pedley, Naylor, et al., 1986
Pedley, J.B.; Naylor, R.D.; Kirby, S.P.,
Thermochemical Data of Organic Compounds, Chapman and Hall, New York, 1986, 1-792. [all data]
Shehatta, 1993
Shehatta, I.,
Heat capacity at constant pressure of some halogen compounds,
Thermochim. Acta, 1993, 213, 1-10. [all data]
Kurbatov, 1948
Kurbatov, V.Ya.,
Heat capacity of liquids. 2. Heat capacity and the temperature dependence of heat capacity from halogen derivatives of acylic hydrocarbons,
Zh. Obshch. Kim., 1948, 18, 372-389. [all data]
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]
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]
Notes
Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Henry's Law data, Gas phase ion energetics data, 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 Tboil Boiling point Tc Critical temperature Tfus Fusion (melting) point d(ln(kH))/d(1/T) Temperature dependence parameter for Henry's Law constant k°H Henry's Law constant at 298.15K ΔfH°gas Enthalpy of formation of gas at standard conditions ΔfH°liquid Enthalpy of formation of liquid 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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