A combined structural and computational investigation of aminobenzylnaphthol compounds derived from the Betti reaction using valine methyl ester

Abstract

The crystal structures of racemic and (S,S)-aminobenzylnaphthol compounds, obtained via the Betti reaction between 2-naphthol, aryl aldehydes and valine methyl ester, were investigated using X-ray diffraction measurements. The molecular shapes of these molecules are similar with variation in hydrogen/fluorine/chlorine, but different crystallographic assemblies were observed. It is worth pointing out that the racemic fluorinated compound crystallizes as a conglomerate. The lattice energies of the crystal structures were calculated by means of the CrystalExplorer17 program. The main weak interactions assembling the crystal structures were recognized, and their contributions were analyzed using the calculated energetic data. It is interesting to point out the situation, which has seldom been reported in the literature, that CH⋯π interactions play a role, despite the presence of potential hydrogen-bonding donors and acceptors.