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n→π* Interactions Are Competitive with Hydrogen Bonds

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journal contribution
posted on 13.07.2016, 00:00 by Robert W. Newberry, Samuel J. Orke, Ronald T. Raines
Because carbonyl groups can participate in both hydrogen bonds and n→π* interactions, these two interactions likely affect one another. Herein, enhancement of an amidic n→π* interaction is shown to reduce the ability of β-keto amides to tautomerize to the enol, indicating decreased hydrogen-bonding capacity of the amide carbonyl group. Thus, an n→π* interaction can have a significant effect on the strength of a hydrogen bond to the same carbonyl group.