1-Propene, 3-iodo-
- Formula: C3H5I
- Molecular weight: 167.9763
- IUPAC Standard InChIKey: HFEHLDPGIKPNKL-UHFFFAOYSA-N
- 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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Gas phase thermochemistry data
Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, 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: Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔfH°gas | 99.5 | kJ/mol | Ion | Traeger, 1984 | |
ΔfH°gas | 89.8 ± 1.4 | kJ/mol | Eqk | Rodgers, Golden, et al., 1966 | |
ΔfH°gas | 93.3 ± 6.3 | kJ/mol | Cm | Gellner and Skinner, 1949 | Heay 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 | 55.2 ± 5.4 | kJ/mol | Cm | Gellner and Skinner, 1949 | Heay 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 |
---|---|---|---|---|---|
Tboil | 376.2 | K | N/A | Weast and Grasselli, 1989 | BS |
Tboil | 375. | K | N/A | American Tokyo Kasei, 1988 | BS |
Tboil | 374.95 | K | N/A | Lecat, 1943 | Uncertainty assigned by TRC = 0.35 K; TRC |
Tboil | 375. | K | N/A | Lecat, 1927 | Uncertainty assigned by TRC = 1. K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
Tfus | 176. | K | N/A | Timmermans, 1921 | Uncertainty assigned by TRC = 0.5 K; TRC |
Tfus | 173.9 | K | N/A | Timmermans, 1921 | Uncertainty assigned by TRC = 0.5 K; TRC |
Quantity | Value | Units | Method | Reference | Comment |
ΔvapH° | 38. ± 2. | kJ/mol | V | Gellner and Skinner, 1949 | Heay of formation derived by Cox and Pilcher, 1970; ALS |
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
By formula: HI + C3H5I = C3H6 + I2
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -33.3 ± 1.4 | kJ/mol | Eqk | Rodgers, Golden, et al., 1966 | gas phase; ALS |
ΔrH° | -39.7 ± 4.2 | kJ/mol | Eqk | Rodgers, Golden, et al., 1966 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -34.9 ± 0.96 kJ/mol; At 527 K; ALS |
C3H4I- + =
By formula: C3H4I- + H+ = C3H5I
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1551. ± 8.8 | kJ/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; Stronger than MeCN, near FCH2CH2OH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1520. ± 8.4 | kJ/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; Stronger than MeCN, near FCH2CH2OH; B |
By formula: C3H5I + H2O = HI + C3H6O
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -8.79 | kJ/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrolysis; ALS |
By formula: C3H5I = C3H5I
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | -2. | kJ/mol | Eqk | Alfassi, Golden, et al., 1973 | gas phase; ALS |
By formula: C3H5I = C3H5I
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 5.0 | kJ/mol | Eqk | Alfassi, Golden, et al., 1973 | gas 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 |
---|---|---|---|
9.27 | PI | Traeger, 1984, 2 | LBLHLM |
9.30 | PE | Schmidt and Schweig, 1973 | LLK |
9.37 | PE | Boschi and Salahub, 1972 | LLK |
9.298 | S | Boschi and Salahub, 1972 | LLK |
9.25 | PE | Worrell, 1974 | Vertical value; LLK |
9.32 | PE | Boschi and Salahub, 1974 | Vertical value; LLK |
9.30 | PE | Mines and Thompson, 1973 | Vertical value; LLK |
Appearance energy determinations
Ion | AE (eV) | Other Products | Method | Reference | Comment |
---|---|---|---|---|---|
C3H5+ | 9.80 | I | PI | Traeger, 1984, 2 | LBLHLM |
C3H5+ | 9.9 ± 0.1 | I | EI | Burgers, Holmes, et al., 1983 | LBLHLM |
De-protonation reactions
C3H4I- + =
By formula: C3H4I- + H+ = C3H5I
Quantity | Value | Units | Method | Reference | Comment |
---|---|---|---|---|---|
ΔrH° | 1551. ± 8.8 | kJ/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; Stronger than MeCN, near FCH2CH2OH; B |
Quantity | Value | Units | Method | Reference | Comment |
ΔrG° | 1520. ± 8.4 | kJ/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; Stronger than MeCN, near FCH2CH2OH; B |
IR Spectrum
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Data compiled by: Coblentz Society, Inc.
- LIQUID; Not specified, most likely a prism, grating, or hybrid spectrometer.; DIGITIZED BY NIST FROM HARD COPY; 4 cm-1 resolution
- SOLUTION (10% IN CCl4 FOR 3800-1333 AND 10% IN CS2 FOR 1333-400 CM-1); DOW KBr FOREPRISM-GRATING; DIGITIZED BY NIST FROM HARD COPY (FROM TWO SEGMENTS); 4 cm-1 resolution
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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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 | Japan AIST/NIMC Database- Spectrum MS-NW-6072 |
NIST MS number | 229012 |
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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 688. | Helmig and Greenberg, 1995 | 60. 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
Column type | Active phase | I | Reference | Comment |
---|---|---|---|---|
Capillary | DB-1 | 687. | Helmig and Greenberg, 1995 | 60. 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
- Symbols used in this document:
AE Appearance energy Tboil Boiling point Tfus Fusion (melting) point 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 at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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