Enantiospecific Orientation of R–3-Methylcyclohexanone on the Chiral Cu(643)R/S Surfaces

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Abstract

The high Miller index planes of metal single crystals are chiral, if they do not lie perpendicular to any of the mirror symmetry planes of the bulk lattice. Such chiral surfaces of face-centered cubic metals expose kinked step edges and have been shown to have enantiospecific interactions with chiral adsorbates. R–3-methylcyclohexanone (R-3MCHO) exhibits enantiospecific differences in its desorption energies from the R and S chiral kinks on the Cu(643)R/S surfaces. This enantiospecific interaction must also manifest itself in the orientations of R-3MCHO adsorbed at chiral kinks and has been probed by examining the intensities of infrared absorption by R-3MCHO adsorbed at the kinks on the Cu(643)R/S surfaces. Fourier transform infrared reflection−absorption spectra show that the interaction of the R-3MCHO occurs through the carbonyl group which exhibits a red-shift in its stretching mode as a result of adsorption on the surface. The absorption intensities also indicate that the molecule is oriented with the >C═O bond roughly parallel to the surface. More importantly, R-3MCHO adsorbed at the R and the S kinks on the Cu(643)R/S surfaces exhibits different relative absorption intensities of its vibrational modes, clearly indicating that the orientations of R-3MCHO are enantiospecific on the two enantiomorphic surfaces.

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