On the solvolysis kinetics of amidoesters derived from 尾-aminoalcohols

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• 作者：Jamilah N. Hankins ; Michele Gouws ; Amir Mahajer ; Ethan S. Kim ; Kevin P. Gwaltney ; John Haseltine ; ^{jhaselti@kennesaw.edu}
• 关键词：Amidoesters ; Acyl transfer ; Ester solvolysis ; Reaction kinetics
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：9 May, 2012
• 卷：53
• 期：19
• 页码：2450-2453
• 文件大小：286 K

摘要

To better understand reactivity in such systems, fifteen amidoesters derived from 尾-aminoalcohols were solvolyzed at the ester group in mildly basic methanol-d₄. All trials showed pseudo-first-order kinetics by ¹H NMR. The rate constants are about 2 to 140-fold larger than those found with simple alkyl esters. The least bulky N-acyl groups generally sponsor the largest rate constants, and strongly so in two cases, but apparently not as a result of lesser steric crowding between the amide and ester groups. Rate constants are also greater for those amidoesters favoring an anti conformation at the amide linkage.