A potent synthesis and supramolecular synthon hierarchy percipience of (E)-Nʹ-(Napthalen-1-yl-methylene)-benzenesulfonohydrazide and 1-Napthaldehyde: A combined experimental and DFT studies

Abstract

An adduct of (E)-Nʹ-(Napthalen-1-yl-methylene)-benzenesulfonohydrazide (NMBSH) and 1-naphthaldehyde (NAH) was synthesized using an uncomplicated condensation procedure from the NAH and benzenesulfonylhydrazine (BSH) in a good yield (71.0%) and this was crystallized in EtOH. The adduct compound was characterized using spectroscopic techniques such as 1H NMR, 13C NMR, FT-IR and UV–Vis. Structure of adduct was established by using a single crystal X-ray diffraction method (SC-XRDM). The crystallographic parameters are a = 11.87(2)Å, b = 6.75(8)Å and c = 15.87(2)Å, β = 109.62(2)° and it was resolved in monoclinic crystal system and Pc space group. The molecules undergo hydrogen bonding interaction and π-π interaction in the crystal structure of compound. In order to understand the structural and electronic properties, computational calculations of NMBSH and NAH were carried out. All computational based calculations were performed using the DFT at B3LYP (Becke, 3 parameters, Lee-Yang-Parr) theory with 6-31+G (d,p) basis set. Natural bond orbitals (NBOs) analysis was computed at B3LYP/6-311+G (d,p) method. UV-VIS analysis was conducted by TD-DFT/B3LYP/6-31+G (d,p) level. A good agreement was obtained between the experimental and the computational structural data of NMBSH and NAH. The second order perturbation energies have been obtained by NBO analysis, confirmed interactions and strengthen in the intriguing architectures of NMBSH and NAH. With the help of DFT approach, HOMO-LUMO energies were figured out to obtain electronic insights into the NMBSH and NAH. Moreover, information regarding local as well as global chemical activity, nucleophilic and electrophilic nature of NMBSH and NAH has been obtained. Moreover, an excellent agreement was found between experimental and computational UV-VIS findings. The obtained NLO results indicated that our adduct as NMBSH and NAH displayed stronger response than reference molecule. It could be concluded that this study might be helpful for NLO materials.