A mechanistic study on the amidation of esters mediated by sodium formamide

Autor:	Boguslaw Mudryk, Antonio Ramirez, Srinivas Tummala, Rossano Lucius T
Rok vydání:	2011
Předmět:	Formamide Ions Models Molecular Formamides Sodium Methanol Organic Chemistry chemistry.chemical_element Esters Medicinal chemistry Sodium methoxide Solvent chemistry.chemical_compound Kinetics Deprotonation chemistry Tetrahedral carbonyl addition compound Solvents Organic chemistry
Zdroj:	The Journal of organic chemistry. 77(1)
ISSN:	1520-6904
Popis:	Kinetic and computational studies on the amidation of esters with mixtures of formamide and sodium methoxide are described. Rate studies are consistent with a fast deprotonation of formamide followed by two reversible acyl transfers affected by solvent participation. MP2 calculations suggest that the first acyl transfer between the ester and sodium formamide is rate-determining. The transition structures leading to the formation and collapse of the first tetrahedral intermediate are calculated to be isoenergetic.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::8c7077ed23d3a3609ba5b0ec52f47b63 https://pubmed.ncbi.nlm.nih.gov/22087875 Zobrazit plný text záznamu