Aromatic oligoamide foldamers are synthetically derived oligomers that adopt stable secondary structures in solution.   Foldamer design provides a platform for a new direction in biomedical research and has been the focus of a number of research endeavors in the past decade. The design process draws on the principles that govern biopolymer shapes and thus then leads to structures that mimic motifs found in biochemical systems.  Among many strategies used in foldamer design, hydrogen bonding (H-bonding) has served as a very effective designing tool due to the strength and directional characteristics found in hydrogen bonding interactions. Previously, intramolecular H-bonding interactions were investigated on ortho-methoxy compounds using ab initio, methods.  In this work, we investigate ortho-fluoro compounds with a focus on the influence that simultaneous H-bonding has on the cooperativity of the system.  Torsional barriers were calculated and compared between all model compounds, followed by a natural bond orbital study.

Intramolecular hydrogen bonding in aromatic oligoamide foldamers

243rd National Meeting (2012)

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