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  • Title: From uncharged to decacationic molecules: syntheses and spectroscopic properties of heteroarenium-substituted pyridines.
    Author: Schmidt A, Mordhorst T, Nieger M.
    Journal: Org Biomol Chem; 2005 Oct 21; 3(20):3788-93. PubMed ID: 16211115.
    Abstract:
    Nucleophilic substitutions on pentachloropyridine with 4-(dimethylamino)pyridine, 4-aminopyridine, and 4-(pyrrolidin-1-yl)pyridine give mono-, tri- and pentacationic pyridine-hetarenium salts. The mono-, tri- and pentacationic 4-aminopyridine derivatives can be deprotonated to neutral compounds in solution, or protonated to di-, hexa- and decacationic pyridine derivatives, respectively. Successive substitutions with different heteroaromatic nucleophiles give pyridines with two distinct types of heteroarenium substituents.
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