Enantioselective chemisorption of propylene oxide on a 2-butanol modified Pd(111) surface: the role of hydrogen-bonding interactions.
The enantioselective chemisorption of R- and S-propylene oxide has been measured either on clean Pd(111) that has been exposed to S-2-butanol at various temperatures to vary the proportion of 2-butanol and 2-butoxide species or by adsorbing S-2-butanol on oxygen-covered Pd(111) to form exclusively 2-butoxide. The results reveal that enantioselective chemisorption is only found when 2-butanol is present on the surface. This is ascribed to enantiospecific hydrogen-bonding interactions between 2-butanol and propylene oxide. Measurements of the variation in enantiospecificity with 2-butanol exposure suggest that propylene oxide can interact either with a single adsorbed 2-butanol molecule or, at higher coverages, with two adsorbed 2-butanol species to form enantioselective sites.
Gao
Feng
F
Department of Chemistry and Biochemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53211, USA.
Wang
Yilin
Y
Burkholder
Luke
L
Tysoe
Wilfred T
WT
D000327:Adsorption; D000440:Butanols / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D006860:Hydrogen Bonding; D013058:Mass Spectrometry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism; D013499:Surface Properties
D000440:Butanols; D004852:Epoxy Compounds; C043958:2-butanol; D010165:Palladium; C009068:propylene oxide