1-Propene, 3-bromo-
- Formula: C3H5Br
- Molecular weight: 120.976
- IUPAC Standard InChIKey: BHELZAPQIKSEDF-UHFFFAOYSA-N
- CAS Registry Number: 106-95-6
- 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: Propene, 3-bromo-; Allyl bromide; 1-Bromo-2-propene; 2-Propenyl bromide; 3-Bromo-1-propene; 3-Bromopropene; 3-Bromopropylene; CH2=CHCH2Br; Bromallylene; UN 1099; NSC 7596
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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 | 47.7 | kJ/mol | Ion | Traeger, 1984 | |
ΔfH°gas | 45.6 ± 6.7 | kJ/mol | Cm | Gellner and Skinner, 1949 | Heat of formation derived by Cox and Pilcher, 1970 |
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 by: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°liquid | 20. | kJ/mol | Cm | Holm, 1973 | Grignard Rx |
ΔfH°liquid | 13. ± 5.9 | kJ/mol | Cm | Gellner and Skinner, 1949 | Heat of formation derived by Cox and Pilcher, 1970 |
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 | 343.6 ± 0.8 | K | AVG | N/A | Average of 7 values; Individual data points |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 154.15 | K | N/A | Timmermans, 1952 | Uncertainty assigned by TRC = 0.6 K; TRC |
Tfus | 153.75 | K | N/A | Timmermans, 1921 | Uncertainty assigned by TRC = 0.3 K; values for .beta.-allyl bromide and .alpha.-trans allyl bromide also are given; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tc | 544.4 | K | N/A | Majer and Svoboda, 1985 | |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 32.85 | kJ/mol | N/A | Majer and Svoboda, 1985 | |
ΔvapH° | 33. ± 2. | kJ/mol | V | Gellner and Skinner, 1949 | Heat of formation derived by Cox and Pilcher, 1970; ALS |
Enthalpy of vaporization
ΔvapH (kJ/mol) | Temperature (K) | Method | Reference | Comment |
---|---|---|---|---|
30.24 | 343.3 | N/A | Majer and Svoboda, 1985 | |
32.2 | 312. | A,EB | Stephenson and Malanowski, 1987 | Based on data from 297. to 338. K. See also Svoboda, Majer, et al., 1977.; AC |
31.7 ± 0.1 | 318. | C | Svoboda, Majer, et al., 1977 | AC |
31.0 ± 0.1 | 330. | C | Svoboda, Majer, et al., 1977 | AC |
30.4 ± 0.1 | 341. | C | Svoboda, Majer, et al., 1977 | 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 |
---|---|---|---|---|---|
318. to 341. | 47.52 | 0.2779 | 544.4 | Majer and Svoboda, 1985 |
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
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
C3H4Br- + =
By formula: C3H4Br- + H+ = C3H5Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1570. ± 8.8 | kJ/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF; near tBuOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1540. ± 8.4 | kJ/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF; near tBuOH; B |
By formula: C3H5Br + H2O = HBr + C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -15. | kJ/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrolysis; ALS |
By formula: C3H5Br = C3H5Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -3.0 ± 0.4 | kJ/mol | Ciso | Abell and Adolf, 1969 | gas phase; HBr catalyst; ALS |
By formula: C3H5Br = C3H5Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1.3 ± 0.50 | kJ/mol | Eqk | Alfassi, Golden, et al., 1973 | gas phase; ALS |
By formula: C3H5Br = C3H5Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 4.5 ± 0.4 | kJ/mol | Eqk | Alfassi, Golden, et al., 1973 | gas phase; ALS |
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 |
---|---|---|---|---|
0.17 | Q | N/A | missing citation give several references for the Henry's law constants but don't assign them to specific species. |
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 compiled as indicated in comments:
B - John E. Bartmess
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
View reactions leading to C3H5Br+ (ion structure unspecified)
Ionization energy determinations
IE (eV) | Method | Reference | Comment |
---|---|---|---|
9.96 | PI | Traeger, 1984, 2 | LBLHLM |
10.0 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
10.01 | PE | Worrell, 1974 | Vertical value; LLK |
10.18 | PE | Schmidt and Schweig, 1973 | Vertical value; LLK |
10.06 | PE | Mines and Thompson, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H5+ | 10.39 | Br | PI | Traeger, 1984, 2 | LBLHLM |
De-protonation reactions
C3H4Br- + =
By formula: C3H4Br- + H+ = C3H5Br
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1570. ± 8.8 | kJ/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF; near tBuOH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1540. ± 8.4 | kJ/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF; near tBuOH; B |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- GAS (70 mmHg, N2 ADDED, TOTAL PRESSURE 600 mmHg); DOW KBr FOREPRISM-GRATING; DIGITIZED BY COBLENTZ SOCIETY (BATCH II) FROM HARD COPY; 2 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1340 AND 10% IN CS2 FOR 1340-400 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 4000-1330 CM-1, 10% IN CS2 FOR 1330-600 CM-1); BECKMAN IR-7 (GRATING); DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director
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
View image of digitized spectrum (can be printed in landscape orientation).
Due to licensing restrictions, this spectrum cannot be downloaded.
Owner | NIST Mass Spectrometry Data Center Collection (C) 2014 copyright by the U.S. Secretary of Commerce on behalf of the United States of America. All rights reserved. |
---|---|
Origin | NIST Mass Spectrometry Data Center, 1990. |
NIST MS number | 118538 |
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, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
Traeger, 1984
Traeger, J.C.,
A study of the allyl cation thermochemistry by photoionization mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259-271. [all data]
Gellner and Skinner, 1949
Gellner, O.H.; Skinner, H.A.,
Dissociation energies of carbon-halogen bonds. The bond strengths allyl-X and benzyl-X,
J. Chem. Soc., 1949, 1145-1148. [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]
Holm, 1973
Holm, T.,
Thermochemistry of Grignard reagents. Enthalpies of formation of alkylmagnesium bromides and of alkyl bromides,
J. Organomet. Chem., 1973, 56, 87-93. [all data]
Timmermans, 1952
Timmermans, J.,
Freezing points of organic compounds. VVI New determinations.,
Bull. Soc. Chim. Belg., 1952, 61, 393. [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]
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]
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]
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]
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]
Abell and Adolf, 1969
Abell, P.I.; Adolf, P.K.,
HBr catalyzed photoisomerization of allyl halides,
J. Chem. Thermodyn., 1969, 1, 333-338. [all data]
Alfassi, Golden, et al., 1973
Alfassi, Z.B.; Golden, D.M.; Benson, S.W.,
The thermochemistry of the isomerization of 3-halopropenes (allyl halides) to 1-halopropenes; entropy and enthalpy of formation contribution of the Cd-(H)(X) group,
J. Chem. Thermodyn., 1973, 5, 411-420. [all data]
Traeger, 1984, 2
Traeger, J.C.,
A study of the allyl cation thermochemistry by photoionization mass spectrometry,
Int. J. Mass Spectrom. Ion Processes, 1984, 58, 259. [all data]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]
Worrell, 1974
Worrell, C.W.,
The photoelectron and absorption spectra of allyl halides,
J. Electron Spectrosc. Relat. Phenom., 1974, 3, 359. [all data]
Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A.,
Semiquantitative proof of hyperconjugation,
Angew. Chem. Int. Ed. Engl., 1973, 12, 307. [all data]
Mines and Thompson, 1973
Mines, G.W.; Thompson, H.W.,
Photoelectron spectra of vinyl and allyl halides,
Spectrochim. Acta Part A, 1973, 29, 1377. [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, IR Spectrum, Mass spectrum (electron ionization), NIST Free Links, References
- Symbols used in this document:
AE Appearance energy 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 ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions ΔvapH Enthalpy of vaporization ΔvapH° Enthalpy of vaporization at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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