Allyl chloride
- Formula: C3H5Cl
- Molecular weight: 76.525
- 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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Gas phase ion energetics data
Go To: Top, 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, 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, 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.
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]
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]
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, 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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