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Benzene, 2-propenyl-

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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 compiled as indicated in comments:
B - John E. Bartmess
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C9H10+ (ion structure unspecified)

Ionization energy determinations

IE (eV) Method Reference Comment
8.70PEFu and Dunbar, 1978LLK
7.8 ± 0.1EIKoppel, Schwarz, et al., 1974LLK
8.60PERabalais and Colton, 1973LLK
8.20 ± 0.02PEMaier and Turner, 1973LLK
9.16PEEaton and Traylor, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C9H9+11.6 ± 0.1HEIKoppel, Schwarz, et al., 1974LLK

De-protonation reactions

C9H9- + Hydrogen cation = Benzene, 2-propenyl-

By formula: C9H9- + H+ = C9H10

Quantity Value Units Method Reference Comment
Deltar1540. ± 9.2kJ/molG+TSGlasovac, Eckert-Maksic, et al., 2002gas phase; The PhCH2CH=CH2 HOF by 81CHY/HIM is at least 4 kcal/mol too high in energy; B
Deltar1540. ± 19.kJ/molG+TSDahlke and Kass, 1991gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B
Quantity Value Units Method Reference Comment
Deltar1513. ± 8.8kJ/molIMREGlasovac, Eckert-Maksic, et al., 2002gas phase; The PhCH2CH=CH2 HOF by 81CHY/HIM is at least 4 kcal/mol too high in energy; B
Deltar1513. ± 19.kJ/molIMRBDahlke and Kass, 1991gas phase; Between Et2NOH, Me2CH=NOH. Reprotonation site uncertain.; B

References

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Fu and Dunbar, 1978
Fu, E.W.; Dunbar, R.C., Photodissociation spectroscopy and structural rearrangements in ions of cyclooctatetraene, styrene and related molecules, J. Am. Chem. Soc., 1978, 100, 2283. [all data]

Koppel, Schwarz, et al., 1974
Koppel, C.; Schwarz, H.; Bohlmann, F., Elektronenstossinduzierte fragmentierung von acetylenverbindungen. VIII. Struktur der stabilen und instabilen ionen[C9H9]+ aus isomeren C9H10- kohlenwasserstoffen, Org. Mass Spectrom., 1974, 8, 25. [all data]

Rabalais and Colton, 1973
Rabalais, J.W.; Colton, R.J., Electronic interaction between the phenyl group and its unsaturated substituents, J. Electron Spectrosc. Relat. Phenom., 1973, 1, 83. [all data]

Maier and Turner, 1973
Maier, J.P.; Turner, D.W., Steric inhibition of resonance studied by molecular photoelectron spectroscopy. Part 2. Phenylethylenes, J. Chem. Soc. Faraday Trans. 2, 1973, 69, 196. [all data]

Eaton and Traylor, 1974
Eaton, D.F.; Traylor, T.G., Distortional stabilization in phenyl participations, J. Am. Chem. Soc., 1974, 96, 7109. [all data]

Glasovac, Eckert-Maksic, et al., 2002
Glasovac, Z.; Eckert-Maksic, M.; Dacres, J.E.; Kass, S.R., Gas phase formation of 1-phenylcyclobuten-3-yl and 1- phenylallyl anions and a determination of the allylic C-H acidities and bond dissociation energies of 1-phenylcyclobutene and (E)-1-phen, J. Chem. Soc. Perkin Trans., 2002, 2, 3, 410-415, https://doi.org/10.1039/b111398d . [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]


Notes

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