Synthesis, spectral and chemical reactivity analysis of 2,4-dinitrophenyl hydrazone having pyrrole moiety

Abstract

In this paper we present combined experimental and theoretical study on a newly synthesized ethyl 2-cyano-3-[5-(2,4-dinitrophenyl)-hydrazonomethyl)-1H-pyrrol-2-yl]-acrylate (ECDHPA). Quantum chemical calculations have been performed using HF/6-31G(d,p), B3LYP/6-31G(d,p) and B3LYP/6-31++G(d,p) levels. The results obtained from quantum chemical calculations matches well with the experimental finding. Molecular electrostatic potential (MEP) surface of N17H39⋯O42N37 zone show green color having moderate electrostatic potential indicating hydrogen bonding. For the interactions N17H34⋯O42 electron density and its Laplacian (∇2ρBCP) are in the range 0.051–0.119 a.u., indicating interaction follows the Koch and Popelier criteria. The observed NH (νN17H34) stretch of CHNNH part of molecule at 3262cm−1 indicate the red shift and the involvement in hydrogen bonding. Natural bond orbital (NBO) investigation shows various intramolecular interactions within molecule. Electrophilic charge transfer (ECT) has been calculated to investigate the relative electrophilic or nucleophilic behavior of reactant molecules involved in chemical reaction. The first hyperpolarizability (β0) value of ECDHPA is calculated as 22.42×10−30esu. The solvent-induced effects on the non-linear optical properties (NLO) were studied using self-consistent reaction field (SCRF) method and observed that the β0 value increases as solvent polarity increases. DFT based electronic descriptors analysis reveals that studied molecule is a strong electrophile and it would undergo to form various heterocyclic compounds.