Bifurcated hydrogen bonding to fluorine in an all cis -difluoro-hydroxy array

In this communication, we present an unusual bifurcated hydrogen bonding array between an OH donor and two C-F bond acceptors. This serendipitously discovered model system was observed in several substrates with various electron demands placed on the OH acceptor, and all show a symmetrical C-OH-(F-C)2 hydrogen bonding interaction. We employ NMR and IR spectroscopy, X-ray crystallography and DFT theory to characterize this interesting and potentially biochemically relevant hydrogen bonding format.

Automated summary

In this study, we report an unusual bifurcated hydrogen bonding array between an OH donor and two C-F bond acceptors. This serendipitously discovered model system was observed in several substrates with various electron demands on the OH acceptor, and all exhibit a symmetrical C-OH-(F-C)2 hydrogen bonding interaction. We use NMR and IR spectroscopy, X-ray crystallography, and DFT theory to characterize this interesting and potentially biochemically relevant hydrogen bonding pattern.