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Allyl chloride

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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 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 ± 0.01eVN/AN/AL

Ionization energy determinations

IE (eV) Method Reference Comment
10.05PITraeger, 1984LBLHLM
9.9PEBieri, Asbrink, et al., 1982LBLHLM
10.04 ± 0.01PIBuff, Parr, et al., 1981LLK
10.05PEMines and Thompson, 1973LLK
10.05PEBieri, Asbrink, et al., 1982Vertical value; LBLHLM
10.34PEZverev and Ermolaeva, 1981Vertical value; LLK
10.20PEWorrell, 1974Vertical value; LLK
10.34PESchmidt and Schweig, 1973Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C3H3+13.37 ± 0.08?PIBuff, Parr, et al., 1981LLK
C3H5+11.04ClPITraeger, 1984LBLHLM
C3H5+11.05 ± 0.04ClPIBuff, Parr, et al., 1981LLK

De-protonation reactions

C3H4Cl- + Hydrogen cation = Allyl chloride

By formula: C3H4Cl- + H+ = C3H5Cl

Quantity Value Units Method Reference Comment
Deltar1590. ± 17.kJ/molG+TSDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar1571. ± 8.8kJ/molG+TSPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B
Quantity Value Units Method Reference Comment
Deltar1559. ± 17.kJ/molIMRBDahlke and Kass, 1991gas phase; Between MeOH, EtOH. Reprotonation site uncertain; B
Deltar1540. ± 8.4kJ/molIMRBPoutsma, Nash, et al., 1997gas phase; Between iPrOH, HF, near tBuOH; B

References

Go To: Top, Gas phase ion energetics data, 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]


Notes

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