Inorganic acid-catalyzed tautomerization of vinyl alcohol to acetaldehyde

摘要

The vinyl alcohol-acetaldehyde tautomerization reaction has recently received considerable attention as a potential route for the formation of organic acids in the troposphere (Andrews et al., 2012 [7]). We examine the catalytic effect of inorganic acids in the troposphere (e.g. HNO_3, H_2SO_4 and HClO_4) on the vinyl alcohol-acetaldehyde tautomerization reaction, by means high-level thermochemical procedures. We show that H_2SO_4 and HClO_4 catalysts lead to near-zero reaction barrier heights for the vinyl alcohol → acetaldehyde reaction, and to low reaction barrier heights in the reverse direction (ΔH_(298)~z = 40.6 and 39.5 kJ mol~(-1), respectively).