1-Propene, 3-iodo-

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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
Δfgas99.5kJ/molIonTraeger, 1984 
Δfgas89.8 ± 1.4kJ/molEqkRodgers, Golden, et al., 1966 
Δfgas93.3 ± 6.3kJ/molCmGellner and Skinner, 1949Heay 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
Δfliquid55.2 ± 5.4kJ/molCmGellner and Skinner, 1949Heay 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

Quantity Value Units Method Reference Comment
Tboil376.2KN/AWeast and Grasselli, 1989BS
Tboil375.KN/AAmerican Tokyo Kasei, 1988BS
Tboil374.95KN/ALecat, 1943Uncertainty assigned by TRC = 0.35 K; TRC
Tboil375.KN/ALecat, 1927Uncertainty assigned by TRC = 1. K; TRC
Quantity Value Units Method Reference Comment
Tfus176.KN/ATimmermans, 1921Uncertainty assigned by TRC = 0.5 K; TRC
Tfus173.9KN/ATimmermans, 1921Uncertainty assigned by TRC = 0.5 K; TRC
Quantity Value Units Method Reference Comment
Δvap38. ± 2.kJ/molVGellner and Skinner, 1949Heay of formation derived by Cox and Pilcher, 1970; ALS

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:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
B - John E. Bartmess

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

Hydrogen iodide + 1-Propene, 3-iodo- = Propene + Iodine

By formula: HI + C3H5I = C3H6 + I2

Quantity Value Units Method Reference Comment
Δr-33.3 ± 1.4kJ/molEqkRodgers, Golden, et al., 1966gas phase; ALS
Δr-39.7 ± 4.2kJ/molEqkRodgers, Golden, et al., 1966gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -34.9 ± 0.96 kJ/mol; At 527 K; ALS

C3H4I- + Hydrogen cation = 1-Propene, 3-iodo-

By formula: C3H4I- + H+ = C3H5I

Quantity Value Units Method Reference Comment
Δr1551. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Stronger than MeCN, near FCH2CH2OH; B
Quantity Value Units Method Reference Comment
Δr1520. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Stronger than MeCN, near FCH2CH2OH; B

1-Propene, 3-iodo- + Water = Hydrogen iodide + 2-Propen-1-ol

By formula: C3H5I + H2O = HI + C3H6O

Quantity Value Units Method Reference Comment
Δr-8.79kJ/molCmGellner and Skinner, 1949liquid phase; Heat of hydrolysis; ALS

(E)-1-Iodo-1-propene = 1-Propene, 3-iodo-

By formula: C3H5I = C3H5I

Quantity Value Units Method Reference Comment
Δr-2.kJ/molEqkAlfassi, Golden, et al., 1973gas phase; ALS

(Z)-1-Iodo-1-propene = 1-Propene, 3-iodo-

By formula: C3H5I = C3H5I

Quantity Value Units Method Reference Comment
Δr5.0kJ/molEqkAlfassi, Golden, et al., 1973gas 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 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

Ionization energy determinations

IE (eV) Method Reference Comment
9.27PITraeger, 1984, 2LBLHLM
9.30PESchmidt and Schweig, 1973LLK
9.37PEBoschi and Salahub, 1972LLK
9.298SBoschi and Salahub, 1972LLK
9.25PEWorrell, 1974Vertical value; LLK
9.32PEBoschi and Salahub, 1974Vertical value; LLK
9.30PEMines and Thompson, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H5+9.80IPITraeger, 1984, 2LBLHLM
C3H5+9.9 ± 0.1IEIBurgers, Holmes, et al., 1983LBLHLM

De-protonation reactions

C3H4I- + Hydrogen cation = 1-Propene, 3-iodo-

By formula: C3H4I- + H+ = C3H5I

Quantity Value Units Method Reference Comment
Δr1551. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Stronger than MeCN, near FCH2CH2OH; B
Quantity Value Units Method Reference Comment
Δr1520. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Stronger than MeCN, near FCH2CH2OH; B

IR Spectrum

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compiled by: Coblentz Society, Inc.


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

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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 Japan AIST/NIMC Database- Spectrum MS-NW-6072
NIST MS number 229012

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Gas Chromatography

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), References, Notes

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

Van Den Dool and Kratz RI, non-polar column, temperature ramp

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-1688.Helmig and Greenberg, 199560. m/0.33 mm/0.25 μm, 6. K/min; Tstart: -50. C; Tend: 180. C

Normal alkane RI, non-polar column, custom temperature program

View large format table.

Column type Active phase I Reference Comment
CapillaryDB-1687.Helmig and Greenberg, 199560. m/0.33 mm/0.25 μm; Program: not specified

References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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]

Rodgers, Golden, et al., 1966
Rodgers, A.S.; Golden, D.M.; Benson, S.W., The thermochemistry of the gas phase equilibrium I2 + C3H6 = C3H5I + HI, J. Am. Chem. Soc., 1966, 88, 3194-3196. [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]

Weast and Grasselli, 1989
CRC Handbook of Data on Organic Compounds, 2nd Editon, Weast,R.C and Grasselli, J.G., ed(s)., CRC Press, Inc., Boca Raton, FL, 1989, 1. [all data]

American Tokyo Kasei, 1988
American Tokyo Kasei, TCI American Organic Chemical 88/89 Catalog, American Tokyo Kasei, Portland, OR, 1988, 1610. [all data]

Lecat, 1943
Lecat, M., Azeotropes of Ethyl Urethane and other Azeotropes, C. R. Hebd. Seances Acad. Sci., 1943, 217, 273. [all data]

Lecat, 1927
Lecat, M., New binary azeotropes: 7th list, Ann. Soc. Sci. Bruxelles, Ser. B, 1927, 47, 108-14. [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]

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]

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]

Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A., Semiquantitative proof of hyperconjugation, Angew. Chem. Int. Ed. Engl., 1973, 12, 307. [all data]

Boschi and Salahub, 1972
Boschi, R.A.; Salahub, D.R., The far ultra-violet spectra of some branched chain iodo-alkanes, iodo-cycloalkanes, fluoro-iodoalkanes and iodo-alkenes, Mol. Phys., 1972, 24, 735. [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]

Boschi and Salahub, 1974
Boschi, R.A.A.; Salahub, D.R., The high resolution photoelectron spectra of some iodoalkanes, iodocycloalkanes, iodoalkenes, and fluoroiodohydrocarbons, Can. J. Chem., 1974, 52, 1217. [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]

Burgers, Holmes, et al., 1983
Burgers, P.C.; Holmes, J.L.; Mommers, A.A.; Szulejko, J.E., The collisionally induced dissociation of allyl and 2-propenyl cations, Org. Mass Spectrom., 1983, 18, 596. [all data]

Helmig and Greenberg, 1995
Helmig, D.; Greenberg, J., Artifact formation from the use of potassium-iodide-based ozone traps during atmospheric sampling of trace organic gases, J. Hi. Res. Chromatogr., 1995, 18, 1, 15-18, https://doi.org/10.1002/jhrc.1240180105 . [all data]


Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References