The Doubly Oxidized, Antiaromatic Tetraphenylporphyrin Complex [Li(TPP)][BF4]

The Doubly Oxidized, Antiaromatic Tetraphenylporphyrin Complex [Li(TPP)][BF4]

Oxidation of dilithium tetraphenylporphyrin, Li2(TPP), yields the doubly oxidized porphyrin complex [Li(TPP)][BF4]. Free TPP appears to be unstable. The crystal structure of [Li(TPP)][BF4] reveals that the 16-atom C−N inner ring of the porphyrin consists of alternating single and double bonds. NMR s...

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Veröffentlicht in:Organic letters 2006-05, Vol.8 (11), p.2401-2404
Hauptverfasser: Cissell, Julie A, Vaid, Thomas P, Yap, Glenn P. A
Format: Artikel
Sprache:eng
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Zusammenfassung:Oxidation of dilithium tetraphenylporphyrin, Li2(TPP), yields the doubly oxidized porphyrin complex [Li(TPP)][BF4]. Free TPP appears to be unstable. The crystal structure of [Li(TPP)][BF4] reveals that the 16-atom C−N inner ring of the porphyrin consists of alternating single and double bonds. NMR spectroscopy and nucleus-independent chemical shift (NICS) calculations, in addition to the distortion from planarity observed in the crystal structure, indicate that the 16 π-electron inner C−N ring of the porphyrin is antiaromatic.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol060772l