caa a22 4500 606174389 CHVBK 20210128100737.0 cr unu---uuuuu 210128e20150801xx s 000 0 eng 10.1007/s11244-015-0400-2 doi (NATIONALLICENCE)springer-10.1007/s11244-015-0400-2 Proline-Derived Structural Phases on Cu{311} [Elektronische Daten] [David Madden, Israel Temprano, Stephen Jenkins, Stephen Driver] Structural phases formed by adsorption of l-proline onto a Cu{311} surface in ultra-high vacuum were investigated using reflection-absorption infrared spectroscopy, low-energy electron diffraction and scanning tunnelling microscopy. An ordered structural phase formed by self-assembly of l-prolinate with (2,1;1,2) periodicity, and a transition from pure μ3 bonding to a mixture of μ3 and μ2 bonding with increasing exposure at 300K, were observed. This behaviour has broad parallels with that previously seen with alaninate and glycinate on Cu{311}, but the detailed correlation between structure and bonding, and their evolution during subsequent annealing, are markedly different for prolinate as compared to alaninate and glycinate. At annealing temperatures around 480-490K, a new structural phase with (5,3;4,6) periodicity emerges. We tentatively attribute this to pyrrole-2-carboxylate, formed by dehydrogenation and aromatization of the pyrrolidine ring of prolinate. The observation of equal areas of the two possible mirror domains associated with the two possible adsorbate-substrate bonding enantiomers implies a prochiral intermediate. The Author(s), 2015 Chiral nationallicence Enantioselectivity nationallicence Heterogeneous catalysis nationallicence Self-organization nationallicence Alanine nationallicence Glycine nationallicence Madden David Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK aut Temprano Israel Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK aut Jenkins Stephen Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK aut Driver Stephen Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK aut Topics in Catalysis Springer US; http://www.springer-ny.com 58/10-11(2015-08-01), 591-605 1022-5528 58:10-11<591 2015 58 11244 https://doi.org/10.1007/s11244-015-0400-2 text/html Onlinezugriff via DOI BK010053 XK010053 XK010000 Metadata rights reserved Springer special CC-BY-NC licence nationallicence 1 research-article jats NATIONALLICENCE NATIONALLICENCE NL-springer NATIONALLICENCE 856 40 https://doi.org/10.1007/s11244-015-0400-2 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Madden David Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK aut NATIONALLICENCE 700 1- Temprano Israel Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK aut NATIONALLICENCE 700 1- Jenkins Stephen Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK aut NATIONALLICENCE 700 1- Driver Stephen Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW, Cambridge, UK aut NATIONALLICENCE 773 0- Topics in Catalysis Springer US; http://www.springer-ny.com 58/10-11(2015-08-01), 591-605 1022-5528 58:10-11<591 2015 58 11244