Naslov
Benzocyclopropenyl anion - a stable 8-pi-electron species

Autori
Moore, L. ; Lubinski, R. ; Baschky, M.C. ; Dahlke, G.D. ; Hare, M. ; Arrowood, T. ; Glasovac, Zoran ; Eckert-Maksić, Mirjana ; Kass, S.R.

Izvornik
Journal of organic chemistry (0022-3263) 62 (1997), 21; 7390-7396

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
transform mass-spectrometry; ion-cyclotron resonance; gas-phase; cyclopropenyl anions; antiaromaticity; abinitio

Sažetak
The conjugate base of benzocyclopropene has been generated in the gas phase. Its reactivity and thermodynamic stability were explored. The measured acidity is Delta H degrees(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 cyclopropene 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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA