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Benzocyclopropenyl anion - a stable 8-pi-electron species (CROSBI ID 77587)

Prilog u časopisu | izvorni znanstveni rad | međunarodna recenzija

Moore, L. ; Lubinski, R. ; Baschky, M.C. ; Dahlke, G.D. ; Hare, M. ; Arrowood, T. ; Glasovac, Zoran ; Eckert-Maksić, Mirjana ; Kass, S.R. Benzocyclopropenyl anion - a stable 8-pi-electron species // Journal of organic chemistry, 62 (1997), 21; 7390-7396-x

Podaci o odgovornosti

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

engleski

Benzocyclopropenyl anion - a stable 8-pi-electron species

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.

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

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Podaci o izdanju

62 (21)

1997.

7390-7396-x

objavljeno

0022-3263

Povezanost rada

Kemija

Indeksiranost