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The CF 2 H group, a potential surrogate for the OH group, can act as an unusual hydrogen bond donor, as confirmed by crystallographic, spectroscopic, and computational methods. Here, we demonstrate the bioisosterism of the OH and CF 2 H groups and the important roles of CF 2 -H···O hydrogen bonds in influencing intermolecular interactions and conformational preferences. Experimental evidence, corroborated by theory, reveals the distinctive nature of CF 2 H hydrogen bonding interactions relative to their normal OH hydrogen bonding counterparts.

CF2H, a Hydrogen Bond Donor

CF₂H, a Hydrogen Bond Donor