Synthesize, characterization and topological properties of new hydrazone derivatives

Abstract

New hydrazone derivatives, [2-(Naphthalen-2-yloxy)-1-phenyl-ethylidene]-hydrazine (compound 1) and N-(2,4-Dinitro-phenyl)-N′-[2-(Naphthalen-2-yloxy)-1-phenyl-ethylidene]-hydrazine (compound 2) have been synthesized by solid-state synthesis method. These compounds have been characterized by spectroscopic (FTIR, 1HNMR, 13CNMR) techniques. Quantum chemical calculations have been carried out on these molecular structures. The results of the electrostatic potential (ESP) surface indicate that compound 1 has stronger nucleophilic site while compound 2 has stronger nucleophilic sites. Also, there is a flow of electrons from almost all the parts of the molecule towards the NO2 group attached at the para position in compound 2. The second order perturbation energy E(2) values show that the delocalization interactions involving the lone pair of electrons are much stronger than the other interactions but, the molecular geometries have been stabilized predominantly by the π→π* interaction forces. The Laplacian of electron density ∇2ρBCP profile suggest that co-valent character of the C−H bonds of naphthyl and phenyl rings of compound 2 have been enhanced by the substitution of 2,4-Dinitro Phenyl hydrazine. The ∇2ρBCP values qualitatively have good correlation with the decrement/increment of electron density around some of the carbon nuclei as signalled by the NMR chemical shift positions.