1-Propene, 3-iodo-
- Formula: C3H5I
- Molecular weight: 167.9763
- IUPAC Standard InChI: InChI=1S/C3H5I/c1-2-3-4/h2H,1,3H2
- 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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Reaction thermochemistry data
Go To: Top, References, Notes
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° | -7.96 ± 0.33 | kcal/mol | Eqk | Rodgers, Golden, et al., 1966 | gas phase; ALS |
| ΔrH° | -9.5 ± 1.0 | kcal/mol | Eqk | Rodgers, Golden, et al., 1966 | gas phase; Reanalyzed by Cox and Pilcher, 1970, Original value = -8.33 ± 0.23 kcal/mol; At 527 K; ALS |
C3H4I- + =
By formula: C3H4I- + H+ = C3H5I
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 370.7 ± 2.1 | kcal/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; Stronger than MeCN, near FCH2CH2OH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 363.4 ± 2.0 | kcal/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° | -2.10 | kcal/mol | Cm | Gellner and Skinner, 1949 | liquid phase; Heat of hydrolysis; ALS |
=
By formula: C3H5I = C3H5I
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -0.4 | kcal/mol | Eqk | Alfassi, Golden, et al., 1973 | gas phase; ALS |
=
By formula: C3H5I = C3H5I
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1.2 | kcal/mol | Eqk | Alfassi, Golden, et al., 1973 | gas phase; ALS |
References
Go To: Top, Reaction thermochemistry data, Notes
Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.
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]
Cox and Pilcher, 1970
Cox, J.D.; Pilcher, G.,
Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970, 1-636. [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]
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]
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]
Notes
Go To: Top, Reaction thermochemistry data, References
- Symbols used in this document:
ΔrG° Free energy of reaction at standard conditions ΔrH° Enthalpy of reaction at standard conditions - Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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