Synthesis, spectroscopy and computational studies of some novel π-conjugated vinyl N-alkylated quinolinium salts and their precursor's

Jacek E. Nycz*, Karolina Czyz, Marcin Szala, Jan G. Malecki, George Shaw, Brendan Gilmore, Marek Jon

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

A series of π-conjugated vinyl N-methylated quinolinium salts (3) and their precursor's N-alkylated quinolinium salts (2) were prepared and characterized by NMR, IR, UV-Vis and MS spectroscopy. It was confirmed that the hydroxyl and amino derivatives of vinyl N-methylated quinolinium salts lead to spiro type compounds (4). The syntheses of N-alkylated quinolinium salts were successful, and even multigram scale was achievable. The structures of 1,2-dimethylquinolinium iodide (2a) and 1-ethyl-2-methylquinolinium iodide (2b) were determined by single crystal X-ray diffraction method. NMR spectra showed readily diagnostic H-1 and C-13 signals from methyl and N-alkyl groups for both 2 and 3. The geometries of the studied compounds were optimized in singlet states using the density functional theory (DFT) method with B3LYP functional. In general, the predicted bond lengths and angles are in a good agreement with the values based on the X-ray crystal structure data.

Original languageEnglish
Pages (from-to)416-423
Number of pages8
JournalJournal of Molecular Structure
Volume1106
DOIs
Publication statusPublished - 15 Feb 2016

Keywords

  • Perkin condensation
  • Quinoline
  • Quinolinium salt
  • Spiro
  • Styryl dye
  • Styryl quinolinium salt
  • Vinyl quinolinium salt

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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