4-Br-bicyclo[2.2.2]octane-CO2 anion
- Formula: C9H12BrO2-
- Molecular weight: 232.095
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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
C9H12BrO2- + = C9H13BrO2
By formula: C9H12BrO2- + H+ = C9H13BrO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 337.3 ± 2.2 | kcal/mol | G+TS | Koppel, Mishima, et al., 1993 | gas phase |
| ΔrH° | 337.3 ± 2.2 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 330.3 ± 2.0 | kcal/mol | IMRE | Koppel, Mishima, et al., 1993 | gas phase |
| ΔrG° | 330.3 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
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 |
|---|---|---|---|
| 3.87 ± 0.16 | D-EA | Taft and Topsom, 1987 | value altered from reference due to change in acidity scale |
Protonation reactions
C9H12BrO2- + = C9H13BrO2
By formula: C9H12BrO2- + H+ = C9H13BrO2
| Quantity | Value | Units | Method | Reference | Comment |
|---|---|---|---|---|---|
| ΔrH° | 337.3 ± 2.2 | kcal/mol | G+TS | Koppel, Mishima, et al., 1993 | gas phase |
| ΔrH° | 337.3 ± 2.2 | kcal/mol | G+TS | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
| Quantity | Value | Units | Method | Reference | Comment |
| ΔrG° | 330.3 ± 2.0 | kcal/mol | IMRE | Koppel, Mishima, et al., 1993 | gas phase |
| ΔrG° | 330.3 ± 2.0 | kcal/mol | IMRE | Taft and Topsom, 1987 | gas phase; value altered from reference due to change in acidity scale |
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.
Koppel, Mishima, et al., 1993
Koppel, I.A.; Mishima, M.; Stock, L.M.; Taft, R.W.; Topsom, R.D.,
Acidities of 4-Substituted Benzoic, Bicyclo[2.2.2]Oct-1-yl and Bicyclo[2.2.2]Oct-2-enyl Carboxylic Acids,
J. Phys. Org. Chem., 1993, 6, 12, 685, https://doi.org/10.1002/poc.610061205
. [all data]
Taft and Topsom, 1987
Taft, R.W.; Topsom, R.D.,
The Nature and Analysis of Substituent Effects,
Prog. Phys. Org. Chem., 1987, 16, 1. [all data]
Notes
Go To: Top, Reaction thermochemistry data, Gas phase ion energetics data, References
- Symbols used in this document:
EAneutral Electron affinity of neutral species 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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