Benzocyclopropenyl Anion: A Stable 8π-Electron Species

Lenora Moore, Robin Lubinski, Michael C. Baschky, Gregg D. Dahlke, Michael Hare, Tina Arrowood, Zoran Glasovac, Mirjana Eckert-Maksic, Steven R Kass

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

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 languageEnglish (US)
Pages (from-to)7390-7396
Number of pages7
JournalJournal of Organic Chemistry
Volume62
Issue number21
DOIs
StatePublished - Jan 1 1997

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