Conformational analysis of 2,2-difluoroethylamine hydrochloride: double gauche effect

• Josué M. Silla,
• Claudimar J. Duarte,
• Rodrigo A. Cormanich,
• Roberto Rittner and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2014, 10, 877–882, doi:10.3762/bjoc.10.84

• challenge in organic synthesis and in the development of polar organic compounds with attractive properties [10] and because alkylammonium salts are present in a variety of pharmaceuticals, the present work focuses on describing the conformational isomerism in 2,2-difluoroethylamine hydrochloride. Results

• participation of intramolecular hydrogen bond and hyperconjugation. These findings can be useful to predict the structure and stereochemistry of multifluorinated organic compounds with, e.g., pharmaceutical and/or agrochemical interest. Experimental 2,2-Difluoroethylamine hydrochloride (2) was purchased from

• -difluoroethylamine hydrochloride; gauche effect; hydrogen bonding; Introduction The conformational isomerism of alkylamines devotes interest because intramolecular effects relative to hydrocarbon analogues are affected by the electronegativity of the nitrogen atom and by the basicity of the amino group. However