Benzene, cyclopropyl-

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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:
HL - Edward P. Hunter and Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
MM - Michael M. Meot-Ner (Mautner)
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi

View reactions leading to C9H10+ (ion structure unspecified)

Quantity Value Units Method Reference Comment
Proton affinity (review)834.9kJ/molN/AHunter and Lias, 1998HL
Quantity Value Units Method Reference Comment
Gas basicity802.4kJ/molN/AHunter and Lias, 1998HL

Proton affinity at 298K

Proton affinity (kJ/mol) Reference Comment
832.2Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Gas basicity at 298K

Gas basicity (review) (kJ/mol) Reference Comment
802.5Aue, Guidoni, et al., 2000Experimental literature data re-evaluated by the authors using ab initio protonation entropies; MM

Ionization energy determinations

IE (eV) Method Reference Comment
8.35PEFu and Dunbar, 1978LLK
8.3 ± 0.1EIKoppel, Schwarz, et al., 1974LLK
8.6PEFu and Dunbar, 1978Vertical value; LLK
8.61PEShudo, Kobayashi, et al., 1977Vertical value; LLK
8.66PEPrins, Verhoeven, et al., 1977Vertical value; LLK
8.71PEBruckmann and Klessinger, 1974Vertical value; LLK

Appearance energy determinations

Ion AE (eV) Other Products MethodReferenceComment
C9H9+11.4 ± 0.1HEIKoppel, Schwarz, et al., 1974LLK

De-protonation reactions

C9H9- + Hydrogen cation = Benzene, cyclopropyl-

By formula: C9H9- + H+ = C9H10

Quantity Value Units Method Reference Comment
Δr1631. ± 13.kJ/molG+TSChou, Dahlke, et al., 1993gas phase; Between water, furan; B
Quantity Value Units Method Reference Comment
Δr1599. ± 13.kJ/molIMRBChou, Dahlke, et al., 1993gas phase; Between water, furan; B
Δr1607. ± 13.kJ/molIMRBAndrist, DePuy, et al., 1984gas phase; 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.

Hunter and Lias, 1998
Hunter, E.P.; Lias, S.G., Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update, J. Phys. Chem. Ref. Data, 1998, 27, 3, 413-656, https://doi.org/10.1063/1.556018 . [all data]

Aue, Guidoni, et al., 2000
Aue, D.H.; Guidoni, M.; Betowski, L.D., Ab initio calculated gas-phase basicities of polynuclear aromatic hydrocarbons, Int. J. Mass Spectrom., 2000, 201, 283. [all data]

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]

Shudo, Kobayashi, et al., 1977
Shudo, K.; Kobayashi, T.; Utsunomiya, C., Photoelectron spectral studies on the interaction of three-membered rings with aryl groups, Tetrahedron, 1977, 33, 1721. [all data]

Prins, Verhoeven, et al., 1977
Prins, I.; Verhoeven, J.W.; DeBoer, Th.J.; Worrell, C., Conformational studies on arylcyclopropanes-I, Tetrahedron, 1977, 33, 127. [all data]

Bruckmann and Klessinger, 1974
Bruckmann, P.; Klessinger, M., Photoelektronenspektren organischer verbindungen. V. Wechselwirkung kleiner ringe mit π-systemen, Chem. Ber., 1974, 107, 1108. [all data]

Chou, Dahlke, et al., 1993
Chou, P.K.; Dahlke, G.D.; Kass, S.R., Unimolecular Rearrangements of Carbanions in the Gas Phase .2. Cyclopropyl Anions, J. Chem. Soc. Chem. Comm., 1993, 115, 1, 315, https://doi.org/10.1021/ja00054a045 . [all data]

Andrist, DePuy, et al., 1984
Andrist, A.H.; DePuy, C.H.; Squires, R.R., Structures of ssomeric anions in the gas phase: Arylallyl and arylcyclopropyl anions, J. Am. Chem. Soc., 1984, 106, 845. [all data]


Notes

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