The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated

CR Briggs, MJ Allen, David O'Hagan, DJ Tozer, Alexandra Martha Zoya Slawin, AE Goeta, JA Howard

Research output: Other contribution

107 Citations (Scopus)

Abstract

The energies of the gauche and anti conformers of 2-fluoroethylamine, 2-fluoroethanol and their protonated analogues are calculated using density functional theory. Unlike the non protonated systems, the protonated systems show a strong gauche effect where the C-F and the C-+NH3 or C-F and C-+OH2 bonds are gauche rather than anti to each other. Single crystal X-ray diffraction studies of 2-fluoroethylammonium compounds identify the same conformational preference.

Original languageEnglish
Volume2
DOIs
Publication statusPublished - 2004

Keywords

  • C-F BOND
  • ROTATIONAL-ISOMERISM
  • HYDROGEN-BOND
  • FLUORINE
  • 1,2-DIFLUOROETHANE
  • CONFORMATIONS
  • ENERGIES
  • ACIDS
  • NMR

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