1-Propene, 3-iodo-

• Formula: C₃H₅I
• Molecular weight: 167.9763
• IUPAC Standard InChI: InChI=1S/C3H5I/c1-2-3-4/h2H,1,3H2 Copy

  
• IUPAC Standard InChIKey: HFEHLDPGIKPNKL-UHFFFAOYSA-N Copy
• CAS Registry Number: 556-56-9
• Chemical structure:
  This structure is also available as a 2d Mol file
• Other names: Propene, 3-iodo-; Allyl iodide; 3-Iodo-1-propene; 3-Iodopropene; 3-Iodopropylene; CH2CHCH2I; UN 1723; 2-Propene, 1-iodo
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• Information on this page:
  • Condensed phase thermochemistry data
  • Phase change data
  • Gas phase ion energetics data
  • References
  • Notes
• Other data available:
  • Gas phase thermochemistry data
  • Reaction thermochemistry data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
• Data at other public NIST sites:
  • Gas Phase Kinetics Database
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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

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

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

Appearance energy determinations

De-protonation reactions

C₃H₄I^- +  =

By formula: C₃H₄I^- + H⁺ = C₃H₅I

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

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]

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. [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]

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]

Notes

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• Symbols used in this document:
  

  AE	Appearance energy
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  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 at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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