EXPERIMENTAL CUM THEORETICAL EVALUATION OF MOLECULAR STRUCTURE, VIBRATIONAL SPECTRA, NBO, UV, NMR, OF A BIOACTIVE COMPOUND – PHENOXYACETOHYDRAZIDE

M Sangeetha,R Mathammal

doi:10.29121/granthaalayah.v3.i7.2015.2991

Abstract

Hydrazide-Hydrazone compounds are key species for a range of bioactivities. The first complete density functional theoretical study of Phenoxyacetohydrazide(PAH) is reported. The normal mode frequencies, intensities and the corresponding vibrational assignments were calculated using the GAUSSIAN 09W set of quantum chemistry codes at the DFT/B3LYP levels of theory using the 6-311++G** basis set. Stability of the molecule arising from hyperconjugative interactions has been probed using NBO analysis. 1H and 13C NMR spectra have been analysed and the chemical shifts were calculated using the gauge independent atomic orbital(GIAO) method. The theoretical UV-Vis spectrum and the electronic properties, such as HOMO(Highest occupied molecular orbital) and LUMO (Lowest unoccupied molecular orbital) were performed by time dependent density functional theory(TD-DFT) approach.

Highlights

The role of acid hydrazides as active intermediates in synthetic and pharmaceutical chemistry [1,2,3,4,5,6] has prompt the investigation of the stability and structure of acetohydrazide [7]
Some evidence proposes a pharmacophoric character for the hydrazone moiety present in phenyl hydrazone derivatives in the inhibition of cyclooxygenase [18]
A detailed study about the structure of the molecule is obtained by the computational Density functional theory (DFT)/B3LYP method

Summary

Introduction

The role of acid hydrazides as active intermediates in synthetic and pharmaceutical chemistry [1,2,3,4,5,6] has prompt the investigation of the stability and structure of acetohydrazide [7]. A range of bioactivities are reported for hydrazide-hydrazone compounds, such as antibacterial, anticonvulsant, antimalarial, analgesic, anti-inflammatory, antiplatelet, antifungal, antituberculosis,and anticancer activities [8,9,10,11,12,13]. Antioxidant [19,20,21,22],antiglycation [23,24,25,26] and antileishmanial [27] activity have recently been reported, as well as applications in mass spectrometry [28]. The present work aimed to investigate the structural stability and vibrational assignment of Phenoxyacetohydrazide(PAH). Quantum chemical computations are the newly emerging techniques in resolving the structural chemical

Objectives

Results

Conclusion