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, Gas phase ion energetics data, 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 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° | 379.9 ± 4.1 | kcal/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B |
| ΔrH° | 375.4 ± 2.1 | kcal/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF, near tBuOH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 372.5 ± 4.0 | kcal/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B |
| ΔrG° | 368.0 ± 2.0 | kcal/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° | -19.74 ± 0.09 | kcal/mol | Cm | Beldie, Aelenei, et al., 1982 | liquid phase; ALS |
=
By formula: C3H5Cl = C3H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | -2.38 ± 0.10 | kcal/mol | Ciso | Abell and Adolf, 1969 | gas phase; HBr catalyst; ALS |
=
By formula: C3H5Cl = C3H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 3.5 ± 0.2 | kcal/mol | Eqk | Alfassi, Golden, et al., 1973 | liquid phase; ALS |
=
By formula: C3H5Cl = C3H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 2.6 ± 0.2 | kcal/mol | Eqk | Alfassi, Golden, et al., 1973 | liquid phase; ALS |
Gas phase ion energetics data
Go To: Top, Reaction thermochemistry data, 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 evaluated as indicated in comments:
L - Sharon G. Lias
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
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| IE (evaluated) | 10.05 ± 0.01 | eV | N/A | N/A | L |
Ionization energy determinations
| IE (eV) | Method | Reference | Comment |
|---|---|---|---|
| 10.05 | PI | Traeger, 1984 | LBLHLM |
| 9.9 | PE | Bieri, Asbrink, et al., 1982 | LBLHLM |
| 10.04 ± 0.01 | PI | Buff, Parr, et al., 1981 | LLK |
| 10.05 | PE | Mines and Thompson, 1973 | LLK |
| 10.05 | PE | Bieri, Asbrink, et al., 1982 | Vertical value; LBLHLM |
| 10.34 | PE | Zverev and Ermolaeva, 1981 | Vertical value; LLK |
| 10.20 | PE | Worrell, 1974 | Vertical value; LLK |
| 10.34 | PE | Schmidt and Schweig, 1973 | Vertical value; LLK |
Appearance energy determinations
| Ion | AE (eV) | Other Products | Method | Reference | Comment |
|---|---|---|---|---|---|
| C3H3+ | 13.37 ± 0.08 | ? | PI | Buff, Parr, et al., 1981 | LLK |
| C3H5+ | 11.04 | Cl | PI | Traeger, 1984 | LBLHLM |
| C3H5+ | 11.05 ± 0.04 | Cl | PI | Buff, Parr, et al., 1981 | LLK |
De-protonation reactions
C3H4Cl- + =
By formula: C3H4Cl- + H+ = C3H5Cl
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 379.9 ± 4.1 | kcal/mol | G+TS | Dahlke and Kass, 1991 | gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B |
| ΔrH° | 375.4 ± 2.1 | kcal/mol | G+TS | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF, near tBuOH; B |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 372.5 ± 4.0 | kcal/mol | IMRB | Dahlke and Kass, 1991 | gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B |
| ΔrG° | 368.0 ± 2.0 | kcal/mol | IMRB | Poutsma, Nash, et al., 1997 | gas phase; Between iPrOH, HF, near tBuOH; B |
Gas Chromatography
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, 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 | Petrocol DH | 516. | White, Hackett, et al., 1992 | 100. m/0.25 mm/0.5 μm, He, 1. K/min; Tstart: 30. C; Tend: 220. C |
Normal alkane RI, non-polar column, isothermal
| Column type | Active phase | Temperature (C) | I | Reference | Comment |
|---|---|---|---|---|---|
| Packed | Synachrom | 150. | 495. | Dufka, Malinsky, et al., 1971 | Helium, Synachrom (60-80 mesh); Column length: 1.5 m |
| Packed | Synachrom | 150. | 500. | Dufka, Malinsky, et al., 1971 | Helium, Synachrom (60-80 mesh); Column length: 1.5 m |
Normal alkane RI, non-polar column, temperature ramp
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | OV-101 | 526. | Zenkevich, 2005 | 25. m/0.20 mm/0.10 μm, N2/He, 6. K/min; Tstart: 50. C; Tend: 250. C |
| Capillary | SE-54 | 498. | Huang, Liang, et al., 1996 | 36. m/0.25 mm/0.25 μm, 5. K/min; Tstart: 35. C; Tend: 240. C |
Normal alkane RI, non-polar column, custom temperature program
| Column type | Active phase | I | Reference | Comment |
|---|---|---|---|---|
| Capillary | Polydimethyl siloxanes | 526. | Zenkevich and Chupalov, 1996 | Program: not specified |
References
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, 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]
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]
Bieri, Asbrink, et al., 1982
Bieri, G.; Asbrink, L.; Von Niessen, W.,
30.4-nm He(II) photoelectron spectra of organic molecules,
J. Electron Spectrosc. Relat. Phenom., 1982, 27, 129. [all data]
Buff, Parr, et al., 1981
Buff, R.D.; Parr, A.C.; Jason, A.J.,
The photoionization of allyl chloride from onset to 20 eV,
Int. J. Mass Spectrom. Ion Phys., 1981, 40, 31. [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]
Zverev and Ermolaeva, 1981
Zverev, V.V.; Ermolaeva, L.V.,
Ionization potentials and intramolecular charge transfer. II. The photoelectron spectrum and electronic structure of trichloromethylbenzene,
Zh. Strukt. Khim., 1981, 22, 22. [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]
Schmidt and Schweig, 1973
Schmidt, H.; Schweig, A.,
Semiquantitative proof of hyperconjugation,
Angew. Chem. Int. Ed. Engl., 1973, 12, 307. [all data]
White, Hackett, et al., 1992
White, C.M.; Hackett, J.; Anderson, R.R.; Kail, S.; Spock, P.S.,
Linear temperature programmed retention indices of gasoline range hydrocarbons and chlorinated hydrocarbons on cross-linked polydimethylsiloxane,
J. Hi. Res. Chromatogr., 1992, 15, 2, 105-120, https://doi.org/10.1002/jhrc.1240150211
. [all data]
Dufka, Malinsky, et al., 1971
Dufka, O.; Malinsky, J.; Vladyka, J.,
Sorpcni materialy pro plynovou chromatographii - III,
Chemicky promysl., 1971, 21/46, 9, 459-463. [all data]
Zenkevich, 2005
Zenkevich, I.G.,
Experimentally measured retention indices., 2005. [all data]
Huang, Liang, et al., 1996
Huang, C.; Liang, H.; Han, S.,
The analysis of organic compounds in waste water by gas extraction/thermal desorption/gas chromatography-mass spectrometry,
Chin. J. Chromatogr., 1996, 14, 6, 421-424. [all data]
Zenkevich and Chupalov, 1996
Zenkevich, I.G.; Chupalov, A.A.,
New Possibilities of Chromato Mass Pectrometric Identification of Organic Compounds Using Increments of Gas Chromatographic Retention Indices of Molecular Structural Fragments,
Zh. Org. Khim. (Rus.), 1996, 32, 5, 656-666. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, Gas Chromatography, References
- Symbols used in this document:
AE Appearance energy IE (evaluated) Recommended ionization energy 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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