Abstract
Structural and energetic investigations based on semiempirical PM5 and ab initio HF and MP2 calculations suggested that the self-assembled monolayer of an atropisomeric compound, ( R)- or ( S)-1,1′-binaphthalene-2,2′-dithiol (BNSH), on a gold (1 1 1) surface selectively adsorbs one enantiomer of phenylalanine (Phe), resulting in chiral discrimination, through hydrophobic, cation(− NH 3 + ) –π and NH(Phe)–π (BNSH) interactions in a nanometer-sized screw-hole-like pocket composed of three BNSH molecules in the monolayer.
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