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

doi:10.1021/jo9709716

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

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-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 language	English (US)
Pages (from-to)	7390-7396
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	62
Issue number	21
DOIs	https://doi.org/10.1021/jo9709716
State	Published - 1997

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title = "Benzocyclopropenyl Anion: A Stable 8π-Electron Species",

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.",

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

year = "1997",

doi = "10.1021/jo9709716",

language = "English (US)",

volume = "62",

pages = "7390--7396",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Benzocyclopropenyl Anion

T2 - A Stable 8π-Electron Species

AU - Moore, Lenora

AU - Lubinski, Robin

AU - Baschky, Michael C.

AU - Dahlke, Gregg D.

AU - Hare, Michael

AU - Arrowood, Tina

AU - Glasovac, Zoran

AU - Eckert-Maksic, Mirjana

AU - Kass, Steven R

PY - 1997

Y1 - 1997

N2 - 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.

AB - 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.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

Benzocyclopropenyl Anion: A Stable 8π-Electron Species

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