Oxidative nitration reaction of antiaromatic 5,15-dioxaporphyrin

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

Research output: Contribution to journalArticle

Abstract

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
JournalJournal of Porphyrins and Phthalocyanines
DOIs
Publication statusAccepted/In press - Jan 1 2019

Fingerprint

Nitration
Nitro Compounds
Electrons
Electrochemistry
Oxidants
Discrete Fourier transforms
Electronic structure
Protons
Oxidation
nitrosonium ion

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Oxidative nitration reaction of antiaromatic 5,15-dioxaporphyrin. / Nishiyama, Akihide; Tanaka, Yuki; Mori, Shigeki; Furuta, Hiroyuki; Shimizu, Soji.

In: Journal of Porphyrins and Phthalocyanines, 01.01.2019.

Research output: Contribution to journalArticle

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AU - Shimizu, Soji

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