Investigation of the interaction between a novel unnatural chiral ligand and reactant on palladium for asymmetric hydrogenation

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We report about the mechanistic studies of the reaction between a newly synthesized (S)-2-((R)-3H-dinaphtho[2,1-c:1',2'-e]azepin-4(5H)-yl)-2-phenylethanol based on the binaphthyl skeleton and (E)-2-methyl-5- phenylpent-2-enoic acid for the asymmetric hydrogenation of alpha,beta-unsaturated acids with heterogeneous palladium catalysts. The specific interactions between the chiral ligand and reactant were investigated in solution with palladium nanoparticles, as well as under ultrahigh vacuum (UHV) conditions on the palladium metal surface in the absence of hydrogen. The reactions were explored using nuclear magnetic resonance (NMR) spectroscopy, scanning tunneling microscopy (STM), and high-resolution photoemission spectroscopy (HRPES) combined with density functional theory (DFT) calculations. A NMR study identified the interaction between both molecules with palladium nanoparticles in solution. In addition, STM and HRPES studies revealed the spatial distribution and configuration of both compounds on the palladium metal surface under UHV conditions. The theoretical results support the experimental results with respect to the interaction energy value. It was found that the reaction between the ligand and reactant occurs with hydrogen bonding on palladium surface, simultaneously. The present study provides mechanistic details of the asymmetric hydrogenation reaction, which bears a correlation between the ligand, reactant, and catalyst during the reaction.
Publisher
ROYAL SOC CHEMISTRY
Issue Date
2015
Language
English
Article Type
Article
Keywords

ENANTIOSELECTIVE HETEROGENEOUS CATALYSIS; RAY PHOTOELECTRON-SPECTROSCOPY; SUBSTRATE-MODIFIER INTERACTION; MODIFIED PLATINUM; METHYL PYRUVATE; ORGANIC-MOLECULES; METAL-SURFACES; ADSORPTION; PD(111); CINCHONIDINE

Citation

PHYSICAL CHEMISTRY CHEMICAL PHYSICS, v.17, no.27, pp.17771 - 17777

ISSN
1463-9076
DOI
10.1039/c5cp01896j
URI
http://hdl.handle.net/10203/204065
Appears in Collection
CH-Journal Papers(저널논문)
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