Synthesis, Hammett Spectral Correlations and Antimicrobial Activities of (<i>E</i>)-1-Benzylidene-2-(4-Chlorophenyl)Hydrazines

Abstract

ABSTRACT. In the present study, a series of nine number of (E)-1-benzylidene-2-(4-chlorophenyl)hydrazine compounds have been synthesized by condensation reaction of meta and para substituted benzaldehydes with 4-chlorophenylhydrazine using acetic acid catalyst. They are characterized by their physical constants, UV (200-450 nm), Infra-Red (KBr, 4000-400 cm −1 ) and NMR ( 1 H and 13 C) spectral data. The observed UV, IR and NMR spectral data have been correlated with Hammett substituent constants and Swain-Lupton's F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis the effects of substituents on the spectral data have been discussed. The antimicrobial activities of all the synthesized (E)-1-benzylidene-2-(4-chlorophenyl)hydrazine compounds have been studied using Bauer-Kirby method. IntroductionHydrazones are a class of organic compounds in the Schiff base family [1]. They are constitute a versatile compound of organic class having the basic structure R 1 R 2 C=NNR 3 R 4 [2-3]. The two nitrogen atoms of hydrazone are nucleophilic but the amino type nitrogen is more reactive, whereas the carbon atom possesses both characters, that is, nucleophilic and electrophilic. The active centres of hydrazine, that is, carbon and nitrogen, are mainly responsible for the physical and chemical properties of the hydrazones and due to the reactivity toward electrophiles and nucleophiles, hydrazones are used for the synthesis of organic compound such as heterocyclic compounds [4][5] .The general method for the synthesis of the hydrazones is the reaction of hydrazine with carbonyl compounds such as aldehydes or ketones in solvents like ethanol, methanol, butanol [6][7][8] [29]. From through literature survey it is observed that there is no report on the effect of substituents QSAR or QPR study with these (E)-1-benzylidene-2-(4-chlorophenyl)hydrazines, in the past. Therefore the authors take effort to synthesis some substituted (E)-1-benzylidene-2-(4-chlorophenyl)hydrazines and study the correlation analysis with their UV, IR and NMR spectral data and study their antimicrobial activities by using disc diffusion technique.

Synthesis, Characterization, Single-Crystal X-ray Structure and Biological Activities of [(Z)-N′-(4-Methoxybenzylidene)benzohydrazide–Nickel(II)] Complex

“…The synthesis of hydrazones and their metal complexes has attracted considerable scientific interest [1]. They are an essential class of biologically active compounds with unique properties, and they exhibit a broad spectrum of physiological and pharmacological activities [2].…”

Synthesis and antimicrobial activities of some (E)-N'-1-(substituted benzylidene)benzohydrazides

“…Direct attack against cellular constituents are found to be responsible for many diseases including central nerv- Recently, the observations of hetero aromatic hydrazone are authenticating the association of this microorganism with various communicable diseases in human such as food-poisoning associated periodontitis (Tuazon 1995). The above view, some information only available in literature in the previous synthesis and antimicrobial evaluations of aromatic hydrazone compounds (Rajarajan et al 2015). Therefore the authors have taken efforts for the synthesis of (E)-N-1-(substituted benzylidene) benzohydrazides to study the conformation and antibacterial and antifungal activities.…”

Synthesis, spectral LFER and antimicrobial activities of some (E)-N׳-(1-(substituted phenyl)ethylidene)benzohydrazides

“…The spatial arrangement of vinyl and heterocyclic ring protons were confirmed by proton NMR spectra [29][30][31][32]. Recently Rajarajan et al have studied the spectral correlation study of some (E)-1-benzylidene-2-(4-chlorophenyl)hydrazines [33]. Vijayakumar et al have studied the spectral correlation analysis of some substituted(E)-2-benzylidene hydrazinecarbothio amides and observed satisfactory and good correlation coefficients in single and multi-parameter correlations [34].…”