From uncharged to decacationic molecules: syntheses and spectroscopic properties of heteroarenium-substituted pyridines.
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.
Schmidt
Andreas
A
Clausthal University of Technology, Institute of Organic Chemistry, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany. schmidt@ioc.tu-clausthal.de
Mordhorst
Thorsten
T
Nieger
Martin
M
D002412:Cations / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008958:Models, Molecular; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D012680:Sensitivity and Specificity; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013055:Spectrophotometry, Infrared / Q000379:methods; D013237:Stereoisomerism
D002412:Cations; D011725:Pyridines