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Reactivity of the 3,4,5‐Tridehydropyridinium Cation—An Aromatic σ,σ,σ‐Triradical
Author(s) -
Jankiewicz Bartłomiej J.,
Reece Jennifer N.,
Vinueza Nelson R.,
Nash John J.,
Kenttämaa Hilkka I.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200802714
Subject(s) - reactivity (psychology) , fourier transform ion cyclotron resonance , aryne , chemistry , mass spectrometry , ion , resonance (particle physics) , photochemistry , radical ion , computational chemistry , medicinal chemistry , organic chemistry , atomic physics , medicine , physics , alternative medicine , pathology , chromatography
Seeing the sites : Reactivity studies on the σ,σ,σ‐triradical 3,4,5‐tridehydropyridinium cation by using a Fourier transform ion cyclotron resonance mass spectrometer show that bond formation first occurs at C3 for radical reactions, and at either C3 or C4 for nonradical reactions (see scheme). The isomeric 2,4,6‐tridehydropyridinium cation shows different chemical properties because of the lower reactivity of its meta ‐benzyne group(s) and its greater Brønsted acidity.