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cyclohexanone enolate anion


Reaction thermochemistry 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 by: John E. Bartmess

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Individual Reactions

C6H9O- + Hydrogen cation = Cyclohexanone

By formula: C6H9O- + H+ = C6H10O

Quantity Value Units Method Reference Comment
Deltar366.4 ± 2.0kcal/molD-EABrinkman, Berger, et al., 1993gas phase
Deltar365.8 ± 2.3kcal/molD-EAZimmerman, Jackson, et al., 1978gas phase
Deltar369.0 ± 4.2kcal/molG+TSBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH
Quantity Value Units Method Reference Comment
Deltar358.7 ± 2.3kcal/molH-TSBrinkman, Berger, et al., 1993gas phase
Deltar358.0 ± 2.6kcal/molH-TSZimmerman, Jackson, et al., 1978gas phase
Deltar361.2 ± 4.0kcal/molIMRBBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH

Gas phase ion energetics data

Go To: Top, Reaction thermochemistry 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: John E. Bartmess

Electron affinity of neutral species

EAneutral (eV) Method Reference Comment
1.526 ± 0.010LPDBrinkman, Berger, et al., 1993 
1.552 ± 0.052PDZimmerman, Jackson, et al., 1978 
1.42 ± 0.20D-EABrickhouse and Squires, 1988Between acetone, Me2C=NOH

Protonation reactions

C6H9O- + Hydrogen cation = Cyclohexanone

By formula: C6H9O- + H+ = C6H10O

Quantity Value Units Method Reference Comment
Deltar366.4 ± 2.0kcal/molD-EABrinkman, Berger, et al., 1993gas phase
Deltar365.8 ± 2.3kcal/molD-EAZimmerman, Jackson, et al., 1978gas phase
Deltar369.0 ± 4.2kcal/molG+TSBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH
Quantity Value Units Method Reference Comment
Deltar358.7 ± 2.3kcal/molH-TSBrinkman, Berger, et al., 1993gas phase
Deltar358.0 ± 2.6kcal/molH-TSZimmerman, Jackson, et al., 1978gas phase
Deltar361.2 ± 4.0kcal/molIMRBBrickhouse and Squires, 1988gas phase; Between acetone, Me2C=NOH

References

Go To: Top, Reaction thermochemistry data, 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.

Brinkman, Berger, et al., 1993
Brinkman, E.A.; Berger, S.; Marks, J.; Brauman, J.I., Molecular Rotation and the Observation of Dipole-Bound States of Anions, J. Chem. Phys., 1993, 99, 10, 7586, https://doi.org/10.1063/1.465688 . [all data]

Zimmerman, Jackson, et al., 1978
Zimmerman, A.H.; Jackson, R.L.; Janousek, B.K.; Brauman, J.J., Electron photodetachment from cyclic enolate anions in the gas phase: Electron affinities of cyclic enolate radicals, J. Am. Chem. Soc., 1978, 100, 4674. [all data]

Brickhouse and Squires, 1988
Brickhouse, M.D.; Squires, R.R., Gas Phase Bronsted vs. Lewis Acid-Base Reactions of 6,6-Dimethylfulvene. A Sensitive Probe of the Electronic Structures of Organic Anions, J. Am. Chem. Soc., 1988, 110, 9, 2706, https://doi.org/10.1021/ja00217a002 . [all data]


Notes

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