Oxidative nitration reaction of antiaromatic 5,15-dioxaporphyrin

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

    研究成果: ジャーナルへの寄稿学術誌査読

    5 被引用数 (Scopus)

    抄録

    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.

    本文言語英語
    ページ(範囲)355-361
    ページ数7
    ジャーナルJournal of Porphyrins and Phthalocyanines
    24
    1-3
    DOI
    出版ステータス出版済み - 1月 1 2020

    !!!All Science Journal Classification (ASJC) codes

    • 化学 (全般)

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