Table 6. Calculated (G3MP2) Acid Dissociation Enthalpies (ΔHACID) for Fulven-7-ol and Related Alcohols (kcal/mol).
| alcohol | ΔHACID (calc)a | ΔHACID (exp)b |
|---|---|---|
| fulven-7-ol (15) | 363.6 | |
| 6-methylfulven-7-ol (4) | 364.7 | |
| 5,6-dihydrofulven-7-ol (17) | 374.5 (324.4)c | |
| 6-methyl-5,6-dihydrofulven-7-ol (19) | 373.0 (341.6)c | |
| heptafulven-9-ol (21) | 367.3 | |
| triafulven-5-ol (23) | 382.9 | |
| fulven-6-ol (25) | 329.3 | |
| cyclopentadiene-5-carboxaldehyde | 329.4 | |
| benzyl alcohol | 369.8 | 370.0 ± 2.1 |
a
The calculated values are corrected for the enthalpy of the proton at STP.
b
Bartmess, J. E. In NIST Standard Reference Database Number 69; Mallard, W. G., Linstrom, P. J., Eds.; National Institute of Standards and Technology: Gaithersburg, MD, 2005 (http://webbook.nist.gov).
c
In these two cases, the more stable alcohol anion results from internal proton transfer from C5 of the 5-membered ring to the oxygen giving a substituted cyclopentadienide anion.