Abstract
The conjugate base of benzocyclopropene has been generated in the gas phase. Its reactivity and thermodynamic stability were explored. The measured acidity is ΔH°acid(benzocyclopropene) = 386 ± 3 kcal/mol, and the electron affinity of benzocyclopropenyl radical is 0.51 eV < EA < 1.11 eV. Ab initio calculations satisfactorily reproduce the experimental results and provide additional insights. Benzocyclopropene is found to be 34.5 kcal/mol more acidic than the allylic position of cyclopropane and only 4 ± 3 kcal/mol less acidic than toluene. These findings are explained in terms of the structure and electronic properties of benzocyclopropenyl anion.
Original language | English (US) |
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Pages (from-to) | 7390-7396 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 62 |
Issue number | 21 |
DOIs | |
State | Published - 1997 |