Real-time mechanistic monitoring of an acetal hydrolysis using ultrafast 2D NMR

Ultrafast (UF) 2D NMR makes it possible to obtain a 2D NMR spectrum in less than a second. Here, UF-HSQC experiments are used for the real-time mechanistic study of an acetal hydrolysis at C-13 natural abundance, and it is possible to characterize the presence of the hemiacetal, an intermediate with a well-known short lifetime. The assignments are confirmed and rationalized by quantum calculations of H-1 and C-13 NMR chemical shifts and natural bonding orbital analysis. Copyright (c) 2012 John Wiley & Sons, Ltd.