AVS 50th International Symposium
    Surface Science Wednesday Sessions
       Session SS-WeP

Paper SS-WeP12
Structure and Reactivity of Methyl Pyruvate and Butane-2,3-Dione on Pt(111) and Ni(111): Relevance to Enantiosective Hydrogenation at Surfaces

Wednesday, November 5, 2003, 11:00 am, Room Hall A-C

Session: Poster Session
Presenter: M.-A. Laliberte, Universite Laval, Canada
Authors: M.-A. Laliberte, Universite Laval, Canada
S. Lavoie, Universite Laval, Canada
P.H. McBreen, Universite Laval, Canada
Correspondent: Click to Email
Methyl and ethyl pyruvate are substrates in one of the rare examples of efficient enantioselective heterogeneous catalysis.@footnote 1,2@ The asymmetric hydrogenation of pryuvates to lactates occurs on chirally-modified supported platinum catalysts. Nickel catalysts are, in contrast, not active for the reaction. Data is now available in the literature for the chemisorption of pyruvates on both Ni(111)@footnote 3,4@ and Pt(111).@footnote 5-8@ An intriguing aspect of these results is that they show that the surface chemistry of pyruvates differs greatly between the two metals. We have previously reported a detailed RAIRS study of the coverage dependent orientation, conformation and surface chemistry of methyl pryuvate on Ni(111).@footnote 3,4@ The present study presents extensive new RAIRS data for methyl pyruvate on Pt(111), and butane-2,3-dione on Ni(111) and Pt(111), thereby enabling a detailed comparison to be made between the two surfaces. @FootnoteText@@footnote 1@Y. Orito, S. Imai, S. Niwa, N. G. Hung, J. Synth. Org. Chem. Jpn. 37, 173 (1979) @footnote 2@H. U. Blaser, H. P. Jalett, W. Lottenbach and M. Studer, J. Am. Chem. Soc. 122, 12675 (2000). @footnote 3@M. Castonguay, J.-R. Roy, S. Lavoie, A. Adnot, and P. H. McBreen, J. Am. Chem. Soc. 123,6429 (2001). @footnote 4@M. Castonguay, J. -R. Roy, A. Rochefort, and P. H. McBreen, J. Am. Chem. Soc. 122, 518 (2000). @footnote 5@T. Burgi, F. Atamny, R. Schlogl and A. Baiker, J. Phys. Chem. B, 104, 5953. (2000). @footnote 6@J. M. Bonello, R. M. Lambert, N. Kunzle and A. Baiker, J. Am. Chem. Soc. 122, 9864 (2000). @footnote 7@J.M.Bonello, E.C.H. Sykes, R. Lindsay, F.J. Williams, A. K. Santra and R.M. Lambert, Surf. Sci. 482 207 (2001) @footnote 8@J. M. Bonello, F. J. Williams, A. K. Santra, and Richard M. Lambert, J. Phys. Chem. B, 104, 9696 (2000).