Methyl pyruvate is a prochiral reactant in the Orito reaction and enantioselectively hydrogenates to methyl lactate on cinchona-modified metal catalysts. As a first step to understanding this reaction, the structure, orientation reactivity and distribution of methyl pyruvate is studied on Pd(111) using a combination of temperature-programmed desorption, infrared spectroscopy and scanning tunneling microscopy(STM).  Molecular methyl pyruvate adsorbs with its molecular plane parallel to the surface at low coverages and converts to a vertical species as the coverage increases. Enol formation is found using STM.  The presence of these species is confirmed using first-principle density functional theory calculations, which are also used to simulate the STM images with both clean and functionalized tips to confirm the nature of the surface molecular species and to explore the effects of tip functionalization on the images.  If time permits, the prochiral interaction between methyl pyruvate and a chiral modifier, a-(1-Naphthyl)ethylamine will be discussed.

Structure, orientation, and distribution of methyl pyruvate on Pd(111)

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.