From uncharged to decacationic molecules: syntheses and spectroscopic properties of heteroarenium-substituted pyridines

Org Biomol Chem. 2005 Oct 21;3(20):3788-93. doi: 10.1039/b510627c. Epub 2005 Sep 14.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cations / chemical synthesis
  • Cations / chemistry
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy / methods
  • Models, Molecular
  • Molecular Structure
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry*
  • Sensitivity and Specificity
  • Spectrometry, Mass, Electrospray Ionization / methods
  • Spectrophotometry, Infrared / methods
  • Stereoisomerism

Substances

  • Cations
  • Pyridines