Facile synthesis of aminoalkyl naphthols and single crystal X-ray, computational studies on 1-[morpholino(thiophen-2-yl)methyl]naphthalen-2-ol

Abstract

• One-pot, three-component organic synthesis. • Single crystal XRD confirms the formation of compound. • Crystalized compound compared with the theoretical calculation of DFT. • The HOMO–LUMO energy gap reveals the chemical stability of the compound. An efficient, eco-friendly protocol is developed for the synthesis of 1- (α-aminoalkyl)-2-naphthol derivatives via one-pot three-component reaction of 2-naphthol, aromatic aldehydes and piperidine or morpholine in the presence of Amberlite IRA-400 Cl resin as a catalyst. This approach carries characteristics of one-pot synthesis, high yield, and mild, clean reaction conditions with the recyclable catalyst. One of the products ( 4p ), crystalized in trigonal crystal system with P32 space group, was obtained and compared with the theoretical calculation of popular Density Functional Theory (DFT), B3LYP/6-311++G(d,p) basis set. The energy of highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) was calculated. All theoretical calculations agree with the experimental values.