19F and 13C GIAO-NMR chemical shifts for the identification of perfluoro-quinoline and -isoquinoline derivatives

Mark A. Fox, Graham Pattison, Graham Sandford, Andrei S. Batsanov

Research output: Contribution to journalArticle

Abstract

Reaction of perfluoroquinoline 1 and perfluoroisoquinoline 2 with benzylamine gave mono- and di-aminated quinoline and isoquinoline systems, respectively, depending upon the reaction conditions by selective S NAr processes. Optimised model geometries of the aminated derivatives at MP2/6-31G* were in very good agreement with available X-ray crystallographic data and were used to compute 19F and 13C GIAO-NMR shifts. Comparison with observed 19F and 13C NMR shifts give excellent correlations, indicating that 19F and 13C GIAO-NMR computations are powerful tools in structurally identifying polyfunctional, polycyclic perfluoroheteroaromatic compounds and aiding NMR resonance assignment.

Original languageEnglish
Pages (from-to)62-71
Number of pages10
JournalJournal of Fluorine Chemistry
Volume155
DOIs
Publication statusPublished - 12 Jun 2013

Keywords

  • NMR spectroscopy
  • Nucleophilic aromatic substitution
  • Perfluoroheteroaromatic
  • Perfluoroquinoline

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