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Nitzer, Alexander ORCID logoORCID: https://orcid.org/0000-0003-4903-9603; Manhart, Pauline; Jessen, Christoph und Kornath, Andreas J. ORCID logoORCID: https://orcid.org/0000-0002-7307-4516 (2024): Diaminomaleonitrile – Mono‐, Di‐ …and Tetraprotonation?! In: European Journal of Organic Chemistry, Bd. 27, Nr. 25, e202400152

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Abstract

The successful mono- and diprotonation of DAMN showed the first site of protonation to be an amino group, while the second protonation occurs at a nitrile group. The prepared salts were characterized by vibrational spectroscopy and single crystal X-ray crystallography. Under strong superacidic conditions and with sufficient time cyclization of two (di)protonated molecules of DAMN is observed, yielding a tetracationic pyrazine species. Quantum chemical calculations are employed to explain reactivity and properties of compounds shown in the manuscript.

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