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
引用
收藏
页数：8
相关论文
共 50 条
  • [31] DETERMINATION OF MONO-, DI-, AND TRICHLORAMINE BY ULTRAVIOLET ABSORPTION SPECTROPHOTOMETRY
    CZECH, FW
    FUCHS, RJ
    ANTCZAK, HF
    ANALYTICAL CHEMISTRY, 1961, 33 (06) : 705 - 707
  • [32] The synthesis of diisobutyl mono-, di- and tri-hydroxyphenols
    Niederl, JB
    Natelson, S
    Beekman, EM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1933, 55 : 2571 - 2575
  • [33] Tensammetry of homogeneous mono-, di- and tri- ethoxydodecylethers
    Borkowska, Magdalena
    Szymanski, Andrzej
    Lukaszewski, Zenon
    CHEMIA ANALITYCZNA, 2007, 52 (06): : 1059 - 1069
  • [34] MONO- DI- AND TRI-ETHANOLAMINE DERIVATIVES OF SAMARIUM
    SANKHLA, BS
    KAPOOR, RN
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (06) : 1381 - +
  • [35] A Rhodium Peroxido Complex in Mono-, Di-, and Peroxygenation Reactions
    Meier, Gregor
    Braun, Thomas
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (14) : 3280 - 3284
  • [36] Complexation of zinc octaalkylporphyrin with mono-, di-, and triethylenediamines in toluene
    Mamardashvili, G. M.
    Mamardashvili, N. Zh.
    Koifman, O. I.
    RUSSIAN JOURNAL OF INORGANIC CHEMISTRY, 2007, 52 (08) : 1215 - 1219
  • [37] Complexation of zinc octaalkylporphyrin with mono-, di-, and triethylenediamines in toluene
    G. M. Mamardashvili
    N. Zh. Mamardashvili
    O. I. Koifman
    Russian Journal of Inorganic Chemistry, 2007, 52 : 1215 - 1219
  • [38] The thermal decomposition of mono-, di-, and tripotassium salts of trinitrophloroglucinol
    Sinditskii, V. P.
    Levshenkov, A. I.
    Kravchenko, V. V.
    Shelaputina, V. P.
    RUSSIAN JOURNAL OF PHYSICAL CHEMISTRY B, 2009, 3 (01) : 46 - 55
  • [39] Amines separation from mono-, di- and trioctylamines mixture
    Elias, A
    Didi, MA
    Villemin, D
    Hamidi, A
    HYDROMETALLURGY, 2002, 63 (01) : 49 - 53
  • [40] π-π Interaction Energies as Determinants of the Photodimerization of Mono-, Di-, and Triazastilbenes
    Parent, Alexander A.
    Ess, Daniel H.
    Katzenellenbogen, John A.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12): : 5448 - 5462
12345