Demonstration of tunable reactivity for meta-benzynes

John J. Nash, Katrina E. Nizzi, Anthony Adeuya, Michael J. Yurkovich, Christopher J. Cramer, Hilkka I. Kenttämaa

Research output: Contribution to journalArticlepeer-review

24 Scopus citations

Abstract

A combined computational and experimental study on the gas-phase structures and reactivities of charged 1,3-didehydroarenes (meta-benzynes) demonstrates that the reactivity of such biradicals can be "tuned" by using appropriate substituents. Substituents that destabilize a specific zwitterionic resonance structure can change the reactivity of the biradical from mildly carbocationic to radical-like. These substituent effects are not the result of changes in the singlet-triplet gaps of the biradicals, but rather reflect changes in the potential energy surfaces for the dehydrocarbon separation.

Original languageEnglish (US)
Pages (from-to)5760-5761
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number16
DOIs
StatePublished - Apr 27 2005

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