Diaminomaleonitrile – Mono‐, Di‐ …and Tetraprotonation?

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 condi...

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Bibliographic Details
Published in:	European journal of organic chemistry Vol. 27; no. 25
Main Authors:	Nitzer, Alexander, Manhart, Pauline, Jessen, Christoph, Kornath, Andreas J.
Format:	Journal Article
Language:	English
Published:	Weinheim Wiley Subscription Services, Inc 01-07-2024
Subjects:	Astrochemistry Crystallography Diaminomaleonitrile Protonation Quantum chemistry Quantumchemistry Single crystals Superacid Tetracation
Online Access:	Get full text
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Summary:	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. DAMN – that's interesting. Mono‐ and diprotonation of diaminomaleonitrile are characterized and discussed. Protonation is possible at either the nitrile or amino moiety. Formed mono‐ and dications are characterized by vibrational spectroscopy and X‐ray diffraction. Experimental observations are supported by quantum chemical calculations. The formation of an aromatic tetracation is discovered and explained.
Bibliography:	Prof. Dr. A. J. Kornath passed away during march 2024.
ISSN:	1434-193X 1099-0690
DOI:	10.1002/ejoc.202400152