Nucleophilic Reactivities of Primary and Secondary Amines in Acetonitrile

✍ Scribed by Tanja Kanzian; Tobias A. Nigst; Andreas Maier; Stefan Pichl; Herbert Mayr

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 595 KB
• Volume: 2009
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.200900925

✦ Synopsis

The kinetics of the reactions of primary and secondary amines with benzhydrylium ions and quinone methides in acetonitrile have been studied under pseudo-first-order conditions (high excess of amines) by UV/Vis spectrophotometry. Generally, the plots of k obs versus amine concentration were linear, in line with a second-order rate law. However, for some reactions of secondary amines with quinone methides, the plots of k obs versus amine concentration showed an upward curvature, which indicates rate-limiting deprotonation of the initially formed adduct by a second molecule of amine.