The trifluoroethylamine group has received much attention as a potential replacement for the peptide bond in the generation of peptidomimetic compounds. In this study, ab initio molecular orbital theory calculations have been performed on analogs of N-methylacetamide generated by replacement of the amide bond by either a trifluoroethylamine or fluoromethylamine group.  Calculations employing a supramolecular approach have been performed on hydrated complexes where a water molecule is associated with the trifluoroethylamine and fluoromethylamine moieties to investigate the ability of these groups to engage in hydrogen bonding. The impact of the fluoro or trifluoromethyl group on proton donating and accepting at nitrogen is also investigated. Several input geometries of hydrated complexes have been considered for each compound under study.  For the complexes found, optimized geometry and binding energy results will be presented.

Fluorinated alkylamine groups as peptide bond mimics:  A computational investigation of hydrogen bonding

243rd National Meeting (2012)

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