Allyl chloride
- Formula: C3H5Cl
- Molecular weight: 76.525
- IUPAC Standard InChI: InChI=1S/C3H5Cl/c1-2-3-4/h2H,1,3H2
- IUPAC Standard InChIKey: OSDWBNJEKMUWAV-UHFFFAOYSA-N
- CAS Registry Number: 107-05-1
- Chemical structure:
This structure is also available as a 2d Mol file or as a computed 3d SD file
The 3d structure may be viewed using Java or Javascript. - Other names: 1-Propene, 3-chloro-; Propene, 3-chloro-; 1-Chloro-2-propene; 2-Propenyl chloride; 3-Chloro-1-propene; 3-Chloropropene; 3-Chloropropylene; CH2=CHCH2Cl; Chloroallylene; Allile(cloruro di); Allylchlorid; Allyle(chlorure d'); Chlorallylene; NCI-C04615; 1-Chloropropene-2; 3-Chloropropene-1; 3-Chlorpropen; α-Chloropropylene; 3-Chloro-1-propylene; UN 1100; NSC 20939; 3-chloropropene (allyl chloride)
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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:
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
C3H4Cl- + =
By formula: C3H4Cl- + H+ = C3H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 1590. ± 17. | kJ/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B |
| ΔrH° | 1571. ± 8.8 | kJ/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF, near tBuOH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 1559. ± 17. | kJ/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B |
| ΔrG° | 1540. ± 8.4 | kJ/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF, near tBuOH; B |
+ 2
=
+
By formula: C3H5Cl + 2C2H7N = C5H11N + C2H8ClN
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -82.6 ± 0.4 | kJ/mol | Cm | Beldie, Aelenei, et al., 1982 | liquid phase; ALS |
=
By formula: C3H5Cl = C3H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -9.96 ± 0.42 | kJ/mol | Ciso | Abell and Adolf, 1969 | gas phase; HBr catalyst; ALS |
=
By formula: C3H5Cl = C3H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 15. ± 0.8 | kJ/mol | Eqk | Alfassi, Golden, et al., 1973 | liquid phase; ALS |
=
By formula: C3H5Cl = C3H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 11. ± 0.8 | kJ/mol | Eqk | Alfassi, Golden, et al., 1973 | liquid 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.
Dahlke and Kass, 1991
Dahlke, G.D.; Kass, S.R.,
Substituent Effects in the Gas Phase - 1-Substituted Allyl Anions,
J. Am. Chem. Soc., 1991, 113, 15, 5566, https://doi.org/10.1021/ja00015a008
. [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]
Beldie, Aelenei, et al., 1982
Beldie, C.; Aelenei, N.; Onu, A.; Nemtoi, G.,
Thermochemical characterization of the reactions involved in the allyldimethylamine synthesis,
Rev. Chim. (Bucharest), 1982, 33, 917-919. [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]
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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