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N??* Interactions Are Competitive with Hydrogen Bonds.

ABSTRACT: Because carbonyl groups can participate in both hydrogen bonds and n??* interactions, these two interactions likely affect one another. Herein, enhancement of an amidic n??* interaction is shown to reduce the ability of ?-keto amides to tautomerize to the enol, indicating decreased hydrogen-bonding capacity of the amide carbonyl group. Thus, an n??* interaction can have a significant effect on the strength of a hydrogen bond to the same carbonyl group.

SUBMITTER: Newberry RW 

PROVIDER: S-EPMC5089869 | biostudies-literature | 2016 Aug

REPOSITORIES: biostudies-literature

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n→π* Interactions Are Competitive with Hydrogen Bonds.

Newberry Robert W RW   Orke Samuel J SJ   Raines Ronald T RT  

Organic letters 20160713 15

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. ...[more]

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