A combined structural and computational investigation of the aminobenzylnaphthols deriving from the Betti reaction with valine methyl ester

The crystal structures of racemic and (S, S)-aminobenzylnaphthols, obtained with a 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 along a hydrogen/fluorine/chlorine variation, but different crystallographic assemblies were observed. It is worth to point 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 contribution was analyzed with the calculated energetic data. It is interesting to point out the situation, seldom reported in the literature, in which CH···π interactions play a role, despite the presence of potential hydrogen bonding donors and acceptors.