Stereoselective Attachment via N Dative Bonding: S-Proline on Ge(100)

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The adsorption configurations of S-proline on Ge(100) were studied using scanning tunneling microscopy (STM), density functional theory (DFT) calculations, and high-resolution photoemission spectroscopy (HRPES). We identified three adsorption structures of S-proline on Ge(100) through analysis of the STM images, DFT calculations, and HRPES results: (i) an "intrarow O-H dissociated and N dative bonded structure", (ii) an "O-H dissociation structure", and (iii) an "N dative bonded structure". Moreover, because adsorption through the N atom of S-proline creates a new chiral center due to symmetry reduction produced by N dative bonding with the surface, the adsorption configurations of S-proline on Ge(100) have either (R,S) or (S,S) chirality. Through DFT calculations, we clearly demonstrated that the adsorption configurations have (R,S) chirality with a preference for reaction at the Re face. This work presents a novel method for generating stereoselective attachment using S-proline molecules adsorbed on a Ge(100) surface.
Publisher
AMER CHEMICAL SOC
Issue Date
2011-01
Language
English
Article Type
Article
Keywords

SCANNING TUNNELING MICROSCOPE; ADSORPTION; CHIRALITY; SURFACES; HYDROGENATION; MOLECULES; CHEMISTRY; INSIGHTS; STYRENE; X-1

Citation

JOURNAL OF PHYSICAL CHEMISTRY C, v.115, no.3, pp.710 - 713

ISSN
1932-7447
DOI
10.1021/jp109633m
URI
http://hdl.handle.net/10203/95576
Appears in Collection
CH-Journal Papers(저널논문)
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