Synthesize, characterization and topological properties of new hydrazone derivatives

What is it about?

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 .

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Why is it important?

Hydrazones are an important class of compounds that have significant chemical properties and applications. Hydrazones which have the common structure – C = N – NH – (R = alkyl or aryl groups) have been widely used in [2 + 2] and [1 + 3] cycloadditions and have a significant role in the synthesis of pyrazoles , and various N, O and S containing heterocyclic compounds such as oxadiazoles, thiazolidines etc. They have also been used as antimicrobial, anti-tubercular agents . Hydrazones exhibit strong coordinating properties towards different metal ions. In addition, aroyl hydrazones and their mode of chelation with transition metal ions present in the living system have been of significant interest . The chemical stability of hydrazones and their high melting point have recently made them attractive new materials which can be used for optoelectronic applications . Phenyl hydrazones have a wide variety of desirable organic nonlinear optical (NLO) properties . The fact that phenyl hydrazones with conjugated organic materials as a part can exhibit large non-linear optical properties has triggered large scale theoretical and experimental investigations in this area . The organic compounds which have an electron donating or withdrawing group capable of interacting through a system of conjugated double bonds showcase high hyperpolarizability which means increased non-linear response of the compounds.

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