1-Propene, 3-bromo-

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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
Δfgas47.7kJ/molIonTraeger, 1984 
Δfgas45.6 ± 6.7kJ/molCmGellner and Skinner, 1949Heat 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
Δfliquid20.kJ/molCmHolm, 1973Grignard Rx
Δfliquid13. ± 5.9kJ/molCmGellner and Skinner, 1949Heat 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
Tboil343.6 ± 0.8KAVGN/AAverage of 7 values; Individual data points
Quantity Value Units Method Reference Comment
Tfus154.15KN/ATimmermans, 1952Uncertainty assigned by TRC = 0.6 K; TRC
Tfus153.75KN/ATimmermans, 1921Uncertainty 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
Tc544.4KN/AMajer and Svoboda, 1985 
Quantity Value Units Method Reference Comment
Δvap32.85kJ/molN/AMajer and Svoboda, 1985 
Δvap33. ± 2.kJ/molVGellner and Skinner, 1949Heat of formation derived by Cox and Pilcher, 1970; ALS

Enthalpy of vaporization

ΔvapH (kJ/mol) Temperature (K) Method Reference Comment
30.24343.3N/AMajer and Svoboda, 1985 
32.2312.A,EBStephenson and Malanowski, 1987Based on data from 297. to 338. K. See also Svoboda, Majer, et al., 1977.; AC
31.7 ± 0.1318.CSvoboda, Majer, et al., 1977AC
31.0 ± 0.1330.CSvoboda, Majer, et al., 1977AC
30.4 ± 0.1341.CSvoboda, Majer, et al., 1977AC

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 341.47.520.2779544.4Majer and Svoboda, 1985 

In addition to the Thermodynamics Research Center (TRC) data available from this site, much more physical and chemical property data is available from the following TRC products:


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- + Hydrogen cation = 1-Propene, 3-bromo-

By formula: C3H4Br- + H+ = C3H5Br

Quantity Value Units Method Reference Comment
Δr1570. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF; near tBuOH; B
Quantity Value Units Method Reference Comment
Δr1540. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF; near tBuOH; B

1-Propene, 3-bromo- + Water = Hydrogen bromide + 2-Propen-1-ol

By formula: C3H5Br + H2O = HBr + C3H6O

Quantity Value Units Method Reference Comment
Δr-15.kJ/molCmGellner and Skinner, 1949liquid phase; Heat of hydrolysis; ALS

1-Propene, 3-bromo- = 1-Propene, 1-bromo-

By formula: C3H5Br = C3H5Br

Quantity Value Units Method Reference Comment
Δr-3.0 ± 0.4kJ/molCisoAbell and Adolf, 1969gas phase; HBr catalyst; ALS

(E)-1-Bromo-1-propene = 1-Propene, 3-bromo-

By formula: C3H5Br = C3H5Br

Quantity Value Units Method Reference Comment
Δr1.3 ± 0.50kJ/molEqkAlfassi, Golden, et al., 1973gas phase; ALS

(Z)-1-Bromo-1-propene = 1-Propene, 3-bromo-

By formula: C3H5Br = C3H5Br

Quantity Value Units Method Reference Comment
Δr4.5 ± 0.4kJ/molEqkAlfassi, Golden, et al., 1973gas 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) = H exp(d(ln(kH))/d(1/T) ((1/T) - 1/(298.15 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)

H (mol/(kg*bar)) d(ln(kH))/d(1/T) (K) Method Reference Comment
0.17 QN/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
9.96PITraeger, 1984, 2LBLHLM
10.0PEBieri, Asbrink, et al., 1982Vertical value; LBLHLM
10.01PEWorrell, 1974Vertical value; LLK
10.18PESchmidt and Schweig, 1973Vertical value; LLK
10.06PEMines and Thompson, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H5+10.39BrPITraeger, 1984, 2LBLHLM

De-protonation reactions

C3H4Br- + Hydrogen cation = 1-Propene, 3-bromo-

By formula: C3H4Br- + H+ = C3H5Br

Quantity Value Units Method Reference Comment
Δr1570. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF; near tBuOH; B
Quantity Value Units Method Reference Comment
Δr1540. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF; near tBuOH; B

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

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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Mass spectrum
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Additional Data

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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

All mass spectra in this site (plus many more) are available from the NIST/EPA/NIH Mass Spectral Library. Please see the following for information about the library and its accompanying search program.


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