Abstract
Abstract The orientation of cinchonidine (CD) adsorbed on a Pt surface, a model system of enantioselective catalysis for hydrogenation reactions, is studied in 1,2-dichloroethane by in situ surface-enhanced infrared absorption spectroscopy in attenuated total reflection configuration. The quinoline (QN) moiety of CD is shown to be reoriented from a π-bonded nearly parallel orientation to an N-bonded upright one by bubbling the solution with H2. The origin of the reorientation is ascribed to the repulsive interaction of a QN π-orbital and the negative surface charge induced by dissociative adsorption of H2 and hydrogenation of the vinyl moiety.
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