Diaminomaleonitrile - Mono-, Di- …and Tetraprotonation?!

被引：0
|
作者：
Nitzer, Alexander [1 ]
Manhart, Pauline [1 ]
Jessen, Christoph [1 ]
Kornath, Andreas J. [1 ]
机构：
[1] Ludwig Maximilians Univ Munchen, Dept Chem & Pharm, Butenandtstr 5-13, D-81377 Munich, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 27卷 / 25期
关键词：
Diaminomaleonitrile; Superacid; Tetracation; Quantumchemistry; Astrochemistry; HYDROGEN; CRYSTAL;
D O I：
10.1002/ejoc.202400152
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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. image
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页数：8
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