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 |
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: Br- + C2H5Br = (Br- • C2H5Br)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50.2 ± 4.2 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
ΔrH° | 48.53 | kJ/mol | TDAs | Dougherty, 1974 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 80.3 | J/mol*K | HPMS | Dougherty, 1974 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 24.7 ± 0.84 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
ΔrG° | 24.7 | kJ/mol | TDAs | Dougherty, 1974 | gas phase; B |
By formula: Cl- + C2H5Br = (Cl- • C2H5Br)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 56.9 ± 4.2 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 29.0 ± 0.84 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
By formula: C2H5Br = HBr + C2H4
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 80.3 ± 2.1 | kJ/mol | Eqk | Lane, Linnett, et al., 1953 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = 79.9 kJ/mol; ALS |
By formula: H2 + C2H5Br = HBr + C2H6
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -59.0 ± 1.1 | kJ/mol | Chyd | Fowell, Lacher, et al., 1965 | gas phase; ALS |
By formula: H2 + 2C2H5Br = 2C2H6 + Br2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 23. ± 13. | kJ/mol | Chyd | Ashcroft, Carson, et al., 1965 | liquid phase; ALS |
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 |
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)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 50.2 ± 4.2 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
ΔrH° | 48.53 | kJ/mol | TDAs | Dougherty, 1974 | gas phase; B,M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrS° | 80.3 | J/mol*K | HPMS | Dougherty, 1974 | gas phase; M |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 24.7 ± 0.84 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
ΔrG° | 24.7 | kJ/mol | TDAs | Dougherty, 1974 | gas phase; B |
By formula: Cl- + C2H5Br = (Cl- • C2H5Br)
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 56.9 ± 4.2 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 29.0 ± 0.84 | kJ/mol | TDAs | Li, Ross, et al., 1996 | gas phase; B |
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
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | OV-1 | 100. | 524. | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | OV-1 | 125. | 529. | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | OV-1 | 75. | 517. | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | SE-30 | 100. | 522. | Winskowski, 1983 | Gaschrom Q; Column length: 2. m |
Packed | Porapack Q | 200. | 484. | Goebel, 1982 | N2 |
Packed | Apolane | 70. | 509.6 | Riedo, Fritz, et al., 1976 | He, Chromosorb; Column length: 2.4 m |
Packed | DC-200 | 100. | 519. | Rohrschneider, 1966 | Column length: 4. m |
Packed | Squalane | 100. | 504. | Rohrschneider, 1966 | Column length: 5. m |
Packed | Apiezon L | 100. | 529. | Rohrschneider, 1966 | Column length: 5. m |
Packed | Apiezon L | 130. | 530. | von Kováts, 1958 | Celite (40:60 Gewichtsverhaltnis) |
Packed | Apiezon L | 70. | 522. | von Kováts, 1958 | Celite (40:60 Gewichtsverhaltnis) |
Kovats' RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Packed | SP-1000 | 100. | 792.57 | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | SP-1000 | 125. | 795.84 | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | SP-1000 | 75. | 777.51 | Castello and Gerbino, 1988 | He, Chromosorb W DMCS; Column length: 3. m |
Packed | Carbowax 20M | 75. | 776. | Goebel, 1982 | N2, Kieselgur (60-100 mesh); Column length: 2. m |
Packed | Carbowax 20M | 100. | 783. | Rohrschneider, 1966 | Column length: 2. m |
Normal alkane RI, non-polar column, temperature ramp
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | OV-101 | 514. | Dimov and Milina, 1989 | H2, 2. K/min; Column length: 50. m; Column diameter: 0.32 mm; Tstart: 40. C; Tend: 280. C |
Normal alkane RI, non-polar column, custom temperature program
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | Polydimethyl siloxanes | 511. | Zenkevich and Chupalov, 1996 | Program: not specified |
Capillary | OV-1, SE-30, Methyl silicone, SP-2100, OV-101, DB-1, etc. | 518. | Waggott and Davies, 1984 | Hydrogen; Column length: 50. m; Column diameter: 0.32 mm; Program: not specified |
Normal alkane RI, polar column, isothermal
Column type | Active phase | Temperature (C) | I | Reference | Comment |
---|---|---|---|---|---|
Capillary | PEG-20M | 100. to 150. | 784. | Wang and Wu, 1990 | N2; Column length: 58. m; Column diameter: 0.35 mm |
References
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, 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]
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
Castello and Gerbino, 1988
Castello, G.; Gerbino, T.C.,
Effect of Temperature on the Gas Chromatographic Separation of Halogenated Compounds on Polar and Non-Polar Stationary Phases,
J. Chromatogr., 1988, 437, 33-45, https://doi.org/10.1016/S0021-9673(00)90369-8
. [all data]
Winskowski, 1983
Winskowski, J.,
Gaschromatographische Identifizierung von Stoffen anhand von Indexziffem und unterschiedlichen Detektoren,
Chromatographia, 1983, 17, 3, 160-165, https://doi.org/10.1007/BF02271041
. [all data]
Goebel, 1982
Goebel, K.-J.,
Gaschromatographische Identifizierung Niedrig Siedender Substanzen Mittels Retentionsindices und Rechnerhilfe,
J. Chromatogr., 1982, 235, 1, 119-127, https://doi.org/10.1016/S0021-9673(00)95793-5
. [all data]
Riedo, Fritz, et al., 1976
Riedo, F.; Fritz, D.; Tarján, G.; Kováts, E.Sz.,
A tailor-made C87 hydrocarbon as a possible non-polar standard stationary phase for gas chromatography,
J. Chromatogr., 1976, 126, 63-83, https://doi.org/10.1016/S0021-9673(01)84063-2
. [all data]
Rohrschneider, 1966
Rohrschneider, L.,
Eine methode zur charakterisierung von gaschromatographischen trennflüssigkeiten,
J. Chromatogr., 1966, 22, 6-22, https://doi.org/10.1016/S0021-9673(01)97064-5
. [all data]
von Kováts, 1958
von Kováts, E.,
206. Gas-chromatographische Charakterisierung organischer Verbindungen. Teil 1: Retentionsindices aliphatischer Halogenide, Alkohole, Aldehyde und Ketone,
Helv. Chim. Acta, 1958, 41, 7, 1915-1932, https://doi.org/10.1002/hlca.19580410703
. [all data]
Dimov and Milina, 1989
Dimov, N.; Milina, R.,
Precalculation of gas chromatographic retention indices of linear 1-halogenoalkanes,
J. Chromatogr., 1989, 463, 159-164, https://doi.org/10.1016/S0021-9673(01)84464-2
. [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]
Waggott and Davies, 1984
Waggott, A.; Davies, I.W.,
Identification of organic pollutants using linear temperature programmed retention indices (LTPRIs) - Part II, 1984, retrieved from http://dwi.defra.gov.uk/research/completed-research/reports/dwi0383.pdf. [all data]
Wang and Wu, 1990
Wang, Z.; Wu, C.,
Volatile matter of Chinese lacquer,
Lin chan hua xue yu gong ye, 1990, 10, 1, 39-41. [all data]
Notes
Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, Gas phase ion energetics data, Ion clustering data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy ΔfH°gas Enthalpy of formation of gas at standard conditions 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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