1.
Org Lett
; 18(15): 3614-7, 2016 08 05.
Artigo
em Inglês
| MEDLINE
| ID: mdl-27409515
RESUMO
Because carbonyl groups can participate in both hydrogen bonds and nâπ* interactions, these two interactions likely affect one another. Herein, enhancement of an amidic nâπ* interaction is shown to reduce the ability of ß-keto amides to tautomerize to the enol, indicating decreased hydrogen-bonding capacity of the amide carbonyl group. Thus, an nâπ* interaction can have a significant effect on the strength of a hydrogen bond to the same carbonyl group.