Oxidative nitration reaction of antiaromatic 5,15-dioxaporphyrin

Akihide Nishiyama, Yuki Tanaka, Shigeki Mori, Hiroyuki Furuta, Soji Shimizu

    Research output: Contribution to journalArticlepeer-review

    9 Citations (Scopus)


    Upon oxidation of 20π-electron antiaromatic 5,15-dioxaporphyrin (DOP) using nitrosonium ions as oxidants, a tetrakis-β-nitrated compound was formed instead of the expected 18π-electron aromatic dication species via an oxidative nitration reaction mechanism. Compared with the original DOP, this tetranitro DOP product exhibited a blue shift of absorption and downfield shifts of the β-pyrrolic proton signals. The unique antiaromatic electronic structure of the tetranitro DOP was disclosed experimentally by electrochemistry and theoretically by DFT and NICS calculations.

    Original languageEnglish
    Pages (from-to)355-361
    Number of pages7
    JournalJournal of Porphyrins and Phthalocyanines
    Issue number1-3
    Publication statusPublished - Jan 1 2020

    All Science Journal Classification (ASJC) codes

    • General Chemistry


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