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Modulating "jousting" C-F---H-C interactions with a bit of hydrogen bonding
Mark D Struble1, Jessica Strull, Kishan Patel
1Department of Chemistry, New Chemistry Building, Johns Hopkins University , 3400 North Charles Street, Baltimore, Maryland 21218, United States.
Abstract:
We have synthesized a series of molecules wherein very close C-F---H-C σ-bond interactions, which we have termed "jousting", can be perturbed through both red- and blue-shifted hydrogen bonding effects. These interactions were induced by the placement of various functional groups geminal to the H-C bond. "Jousting" interactions appear to be an admixture of F---H hydrogen bonding and C-H bond compression. The associated electronic effects from changes in the functional group at the X-position were also studied.
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