“Stereoelectronic Deprotection of Nitrogen”: Recovering Nucleophilicity with a Conformational Change

• Published in: Journal of organic chemistry Vol. 88; no. 11; pp. 6868 - 6877
• Main Authors: Gazizov, Almir S., Smolobochkin, Andrey V., Rizbayeva, Tanzilya S., Vatsadze, Sergey Z., Burilov, Alexander R., Sinyashin, Oleg G., Alabugin, Igor V.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.06.2023; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Lewis bases; moieties; nitrogen; organic chemistry; Physical Sciences; Science & Technology; urea; viability; CATALYSIS; ACYCLIC AMIDES; DONOR; CONSEQUENCES; HYDROLYSIS; PLANAR; BOND; DERIVATIVES; UREA; ACCEPTOR

Ureas are often thought of as “double amides” due to the obvious structural similarity of these functional groups. The main structural feature of an amide is its planarity, which is responsible for the conjugation between the nitrogen atom and carbonyl moiety and the decrease of amide nucleophilicit...