N??* Interactions Are Competitive with Hydrogen Bonds.
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ABSTRACT:
SUBMITTER: Newberry RW
PROVIDER: S-EPMC5089869 | biostudies-literature | 2016 Aug
REPOSITORIES: biostudies-literature
Publications
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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