title: The importance of attractive three-point interaction in enantioselective surface chemistry: stereospecific adsorption of serine on the intrinsically chiral Cu{531} surface.
abstract: Both enantiomers of serine adsorb on the intrinsically chiral Cu{531} surface in two different adsorption geometries, depending on the coverage. At saturation, substrate bonds are formed through the two oxygen atoms of the carboxylate group and the amino group (μ3 coordination), whereas at lower coverage, an additional bond is formed through the deprotonated β-OH group (μ4 coordination). The latter adsorption geometry involves substrate bonds through three side groups of the chiral center, respectively, which leads to significantly larger enantiomeric differences in adsorption geometries and energies compared to the μ3 coordination, which involves only two side groups. This relatively simple model system demonstrates, in direct comparison, that attractive interactions of three side groups with the substrate are much more effective in inducing strong enantiomeric differences in heterogeneous chiral catalyst systems than hydrogen bonds or repulsive interactions.
authors.affiliation: Department of Chemistry, The University of Reading, Whiteknights, Reading, RG6 6AD, United Kingdom.
authors.forename: Tugce
authors.initials: T
authors.lastname: Eralp
authors.forename: Alex
authors.initials: A
authors.lastname: Ievins
authors.forename: Andrey
authors.initials: A
authors.lastname: Shavorskiy
authors.forename: Stephen J
authors.initials: SJ
authors.lastname: Jenkins
authors.forename: Georg
authors.initials: G
authors.lastname: Held
mesh_terms: D000327:Adsorption; D002264:Carboxylic Acids / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D010100:Oxygen / Q000737:chemistry; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism; D013499:Surface Properties
chemical_list: D002264:Carboxylic Acids; D012694:Serine; D003300:Copper; D010100:Oxygen