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 journalArticle

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

Fingerprint Dive into the research topics of 'Benzocyclopropenyl Anion: A Stable 8π-Electron Species'. Together they form a unique fingerprint.

  • Cite this

    Moore, L., Lubinski, R., Baschky, M. C., Dahlke, G. D., Hare, M., Arrowood, T., Glasovac, Z., Eckert-Maksic, M., & Kass, S. R. (1997). Benzocyclopropenyl Anion: A Stable 8π-Electron Species. Journal of Organic Chemistry, 62(21), 7390-7396. https://doi.org/10.1021/jo9709716