Catalysis of Free C-C Bond Rotation: C-F---H-X H-Bonds Find a Catalytic Role
Muyuan Wang1, Aarush Prasad1, Nathaniel G Garrison1
1Department of Chemistry, Johns Hopkins University, 3400 N. Charles St., Baltimore, Maryland 21218, United States.
Abstract:
There are few dynamic processes in organic chemistry that are more central to the molecular structure than C-C bond rotation. It is notable, however, that there exist few (if any) cases in which its hindered variants can actually be catalyzed. In this communication, we report a unique model system for the clear documentation of the catalysis of 360° C-C bond rotation that employs a transient but key N-H---F-C hydrogen bond as a linchpin and secondary "dual" charge-induced n → π* interactions and ion pairing effects that bolster catalysis.
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