Schiff Base Compound Research Articles

Corrosion Inhibition of Carbon Steel by Some Schiff Base Compounds in HCl and H2SO4 Solutions

AbstractThe inhibition power of two Schiff bases on carbon steel corrosion in 1 M HCl and 0.5 M H2SO4 solutions has been investigated using weight loss, Tafel polarization, and electrochemical impedance spectroscopy techniques. The results revealed that increasing the concentration of inhibitors in acidic solutions led to a higher inhibition efficiency. The polarization curves indicated that the Schiff bases acted as mixed inhibitors, affecting both the cathodic and anodic reactions. The adsorption of the inhibitors on the carbon steel surface followed the Langmuir adsorption isotherm, and various adsorption isotherm parameters such as Kads, ΔGads, ΔHads, and ΔSads were determined at room temperature. Furthermore, the effect of temperature on the inhibitors′ performance was examined within the range of 25–45 °C. The corrosion‐related activation energy, pre‐exponential factor (k), activation enthalpy, and entropy were calculated to assess the inhibitors′ behavior. Scanning electron microscopy (SEM) was employed to examine some carbon steel samples, revealing differences in inhibition efficiency attributed to the inhibitors′ chemical structure. The results highlighted the highest inhibition efficiency in H2SO4 medium at 93.4 %, with a corresponding free energy of 39.51 KJ/mol indicating physical‐chemical adsorption of inhibitor molecules. Furthermore, an enthalpy value of −40.6 KJ/mol suggested an exothermic inhibitor absorption process. The findings are presented and discussed in detail.

Synthesis and Antifungal Properties of 1,2,4-Triazole Schiff Base Agents Based on a 3D-QSAR Model.

Based on our previous research, a 3D-QSAR model (q2=0.51, ONC=5, r2=0.982, F=271.887, SEE=0.052) was established to predict the inhibitory effects of triazole Schiff base compounds on Fusarium graminearum, and its predictive ability was also confirmed through the statistical parameters. According to the results of the model design, 30 compounds with superior bioactivity compared to the template molecule 4 were obtained. Seven of these compounds (DES2-6, DES9-10) with improved biological activity and readily available raw materials were successfully synthesized. Their structures were confirmed through HRMS, NMR, and single crystal X-ray diffraction analysis (DES-5). The bioactivity of the final products was investigated through an in vitro antifungal assay. There was little difference in the EC50 values between the experimental and predicted values of the model, demonstrating the reliability of the model. Especially, DES-3 (EC50=9.915 mg/L) and DES-5 (EC50=9.384 mg/L) exhibited better inhibitory effects on Fusarium graminearum compared to the standard drug (SD) triadimenol (EC50=10.820 mg/L). These compounds could serve as potential new fungicides for future research. The interaction between the final products and isocitrate lyase (ICL) was investigated through molecular docking. Compounds with R groups that have a higher electron-donating capacity were found to be biologically active.

Role of galacturonic acid in acrylamide formation: Insights from structural analysis

Acrylamide (AA) is a neoformed compound in heated foods, mainly produced between asparagine (Asn) and glucose (Glc) during the Maillard reaction. Galacturonic acid (GalA), the major component of pectin, exhibits high activity in AA formation. This study investigated the pathway for AA formation between GalA and Asn. Three possible pathways were proposed: 1) The carbonyl group of GalA directly interacts with Asn to produce AA; 2) GalA undergoes an oxidative cleavage reaction to release α-dicarbonyl compounds, which subsequently leads to AA production; 3) 5-formyl-2-furancarboxylic acid, the thermal degradation product of GalA, reacts with Asn to generate AA. Structural analysis revealed that the COOH group in GalA accelerated intramolecular protonation and electron transfer processes, thereby increasing the formation of AA precursors such as decarboxylated Schiff base and α-dicarbonyl compounds, promoting AA formation. This study provides a theoretical basis and new insights into the formation and control of AA.

Zn(II), Mn(III), and Co(III) complexes of Schiff base derived from 2‐hydroxy‐1‐naphthaldehyde: Synthesis, spectral surveys, single crystal structure studies, Hirshfeld surface analysis, density functional theory calculation, molecular electrostatic potential, and molecular docking evaluations

A new series of transition metal complexes of bidentate Schiff base compound derived from 2‐hydroxy‐1‐(2‐methoxyethylimino)‐naphthalene (HL) were synthesized and characterized using elemental analysis, Fourier transform infrared spectroscopy (FT‐IR), and UV–vis spectroscopies. X‐ray single crystal structures of Zn(II), Mn(III), and Co(III) complexes (1–4) have also been determined, and it was indicated that these Zn(II) and Co(III) complexes (1, 4) are in an octahedral geometry. Whereas, it was found that the Zn complex (2) is in quite a regular tetrahedral environment. Also, the Mn center in complex (3) is ligated by two azomethine nitrogen atoms, two ligand oxygen atoms, and one Cl atom of metal salt forming five coordinated tetragonal pyramid geometry around the Mn atoms. The cyclic voltammetry of the complexes specifies an irreversible redox behavior for all complexes (1–4). Next, DFT/B3LYP theoretical method was used to determine the optimal geometrical configurations and comparison between experimental and theoretical data, as well as for calculations of molecular electrostatic potential, highest‐occupied molecular orbital (HOMO)‐lowest‐unoccupied molecular orbital (LUMO) energy values of selected compounds. The study of non‐covalent interactions was done by Hirshfeld surface analysis using CrystalExplorer program. Furthermore, molecular docking inspection was carried out to study the binding affinity of the tested complexes towards protein B‐cell lymphorna (PDB ID: 4LXD). Using the results obtained from the molecular docking and the summarized interaction of the binding processes, these structures show the validity of effective inhibition against liver cancer.

Formulation and Synthesis of Vanillin from Clove Oil as a Chemosensor for Urea Detection in Urine

Urea levels in urine play an important parameter in diagnosing bodily conditions through liver and kidney examinations. The typical reagent for detecting urea content in urine is para-dimethylaminobenzaldehyde (pDMAB). However, it has a drawback related to the instability of color in the resulting Schiff base compound (pDMAB-urea). In this study, the synthesized vanillin compound derived from clove oil serves as the foundational material for a urea chemosensor based on the colorimetric concept. The synthesized vanillin was characterized using FTIR, GC-MS, and 1H-NMR. The formulation of the vanillin compound as a sensor was conducted by assessing the suitable solvent, determining the optimal mass of vanillin, and evaluating the acid-base conditions of the sensor formulation system both qualitatively and quantitatively. Subsequently, the most effective formulation was selected for detecting urea in urine samples. The synthesis of vanillin yielded a purity level of 95%. The optimal formulation was obtained at an optimum mass of vanilla of 0.75 g in 50 mL of 96% ethanol and 10 mL of 10% NaOH. The color change in the sample was from colorless to greenish yellow (436 nm). The vanillin obtained was applied to urine samples with the best results at a sample dilution level of 10,000×.

Molecular docking studies, structural analysis, biological studies, and synthesis of certain novel Schiff base from benzohydrazide derivate

The research described involves the synthesis and characterization of a new benzohydrazide based Schiff base compound namely 4-methyl-N′-(2,4,5-trimethoxybenzylidene) benzohydrazide (HL). The compound was synthesized by condensing a primary amine and an aldehyde functional group. The characterization of the compound was carried out using various spectroscopic techniques, including elemental analysis, Ultraviolet spectroscopy, nuclear magnetic resonance spectroscopy, and infrared spectroscopy. These techniques helped confirm the excellent quality of the synthesized molecules. In addition to the characterization, the Schiff base compound was subjected to docking studies and biological studies. The antibacterial activity of the compound was tested against three strains of bacteria, namely E. faecalis, B. subtills, and E. coli. The results of these tests provided information on the compound effectiveness against these bacterial strains. Furthermore, docking studies was performed to assess the interaction between the synthesized compound and three target enzymes like GlcN-6-p synthase, DNA polymerase, and EGFR tyrosine kinase. Docking studies are computational simulations that provide insights into the binding interactions between Schiff base ligand and target proteins. In this case, the docking studies helped understand the potential mechanisms of action of the synthesized compound by calculating binding constants and the number of binding modes. The biological activity studies revealed interesting fragmentation patterns, which could be further investigated to understand the compound modes of action. Moreover, the docking studies evaluated the compound’s potential as a drug candidate by assessing its binding interactions with the target enzymes. The present study suggests that the synthesized benzohydrazide based Schiff base compound exhibits potential antibacterial activity and shows promising binding interactions with the target protein/enzymes. This information is valuable for designing and developing more potent compounds in the future.

Investigation of illumination-dependent electrical and photodiode properties and conduction mechanism of the Al/p-Si contact with Schiff base compound (Pyr-Pic) interlayer

In this paper, an organic semiconductor, N-(2-((pyren-4-yl)methyleneamino)ethyl)-5- nitropyridin-2-amine (Pyr-Pic), was synthesized and was used as an interfacial organic layer to fabrication of Al/Pyr-Pic/p-Si/Al diode. The device’s characteristic parameters were determined under various operating situations using current–voltage (I-V) measurements. Thermionic emission theory (TE), the Cheung methodology, and Norde functions were the three methods used to determine the device’s electrical properties, such as the ideality factor, barrier height, and series resistance. Based on the I-V measurements conducted under illumination circumstances, the fabricated device exhibits photoresponse properties in the reverse bias region. An examination of the forward log(I)-log(V) plot of the Al/Pyr-Pic/p-Si diode indicated that ohmic conduction dominates carrier transport in the lower bias regions, while the space-charge-limited current (SCLC) governs transport in the medium bias regions, and the trap-charge limit current (TCLC) mechanism is responsible for transport in the higher bias regions. The current voltage mechanisms in the reverse bias area can be characterized by using Poole–Frenkel emission (PFE) and Schottky emission (SE) theories. The device exhibits photovoltaic characteristics when it is illuminated through an Al electrode. The typical photovoltaic parameters were estimated at room temperature and under illumination conditions.

Synthesis, crystal structure and in-silico evaluation of arylsulfonamide Schiff bases for potential activity against colon cancer.

This report presents a comprehensive investigation into the synthesis and characterization of Schiff base compounds derived from benzenesulfonamide. The synthesis process, involved the reaction between N-cycloamino-2-sulfanilamide and various substituted o-salicylaldehydes, resulted in a set of compounds that were subjected to rigorous characterization using advanced spectral techniques, including 1H NMR, 13C NMR and FT-IR spectroscopy, and single-crystal X-ray diffraction. Furthermore, an in-depth assessment of the synthesized compounds was conducted through Absorption, Distribution, Metabolism, Excretion and Toxicity (ADMET) analysis, in conjunction with docking studies, to elucidate their pharmacokinetic profiles and potential. Impressively, the ADMET analysis showcased encouraging drug-likeness properties of the newly synthesized Schiff bases. These computational findings were substantiated by molecular properties derived from density functional theory (DFT) calculations using the B3LYP/6-31G* method within the Jaguar Module of Schrödinger 2023-2 from Maestro (Schrodinger LLC, New York, USA). The exploration of frontier molecular orbitals (HOMO and LUMO) enabled the computation of global reactivity descriptors (GRDs), encompassing charge separation (Egap) and global softness (S). Notably, within this analysis, one Schiff base, namely, 4-bromo-2-{N-[2-(pyrrolidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 20, emerged with the smallest charge separation (ΔEgap= 3.5780 eV), signifying heightened potential for biological properties. Conversely, 4-bromo-2-{N-[2-(piperidine-1-sulfonyl)phenyl]carboximidoyl}phenol, 17, exhibited the largest charge separation (ΔEgap= 4.9242 eV), implying a relatively lower propensity for biological activity. Moreover, the synthesized Schiff bases displayed remarkeable inhibition of tankyrase poly(ADP-ribose) polymerase enzymes, integral in colon cancer, surpassing the efficacy of a standard drug used for the same purpose. Additionally, their bioavailability scores aligned closely with established medications such as trifluridine and 5-fluorouracil. The exploration of molecular electrostatic potential through colour mapping delved into the electronic behaviour and reactivity tendencies intrinsic to this diverse range of molecules.

Exploring Novel Schiff Base Compounds Derived from Benzothiophene-3- carboxaldehyde Hydrazones: In vitro and In silico Evaluation as Potential Inhibitors of Cholinesterases and Carbonic Anhydrases I-II

In this study, inhibitions of some cytosolic enzymes were evaluated. Inhibitors of these enzymes can help illuminate and treat many related diseases (Alzhaimer, Parkinson's, Glaucoma, etc.). It is aimed to minimize drug side effects with multiple effects in one molecule. For this purpose in vitro effects of two benzothiophene Schiff bases on cholinesterases (AChE and BuChE) and human carbonic anhydrase isoforms (CAI and CAII) were investigated. Molecular modeling studies were carried out to elucidate the inhibition mechanism of two effective compounds on these enzymes. Then, two benzothiophene Schiff bases (1a and 1b compounds) were tested in vitro on these enzymes. The in vitro study results supported the in silico study results. Obtained results revealed that the benzothiophene derivatives inhibited the enzymes significantly. Ki values for CAI isoenzyme were determined to be in the range of 58.82 ± 7.96-126.28 ± 26.22 nM; for the CAII isoenzyme in the range of 27.86 ± 3.76-74.30 ± 7.89 nM; for acetylcholinesterase in the range of 1.31 ± 0.39-2.16 ± 1.01 nM; for butyrylcholinesterase in the range of 1.80 ± 0.27-2.01 ± 1.67 nM. Compared to the AZA control compound, 1b has demonstrated more strong inhibitory effect against CAI and CAII. Wherease compared with other control compound Tacrine, both compounds showed more potent inhibitory effect for cholinesterases (AChE and BuChE).

C─H···π interaction induced H‐aggregates for wide range water content detection in organic solvents

AbstractJ‐aggregation and H‐aggregation are identified as two classical models of functionally oriented non‐covalent interactions, and significant attention has been drawn by researchers. However, due to the scarcity of single‐crystal examples of H‐aggregation, a comprehensive understanding of the relationship between its stacking mode and optical behaviour has been hindered. In recent studies, two polyaromatic Schiff base compounds, Cl‐Salmphen and H‐Salmphen, were successfully synthesized, and both were found to exhibit H‐aggregation. In the findings, H‐Salmphen was shown to display typical C─H···π interactions, characteristic of Aggregation‐Induced Emission (AIE) active molecules, whereas its halogenated counterpart was identified as behaving similar to Aggregation‐Caused Quenching (ACQ) active molecules. These types of results suggest that identical intermolecular interactions can produce differing optical behaviours. Light was shed, at least in part, on the formation mechanisms of H‐type aggregates and their luminescence properties from these observations. Additionally, the high optical signal‐to‐noise ratio inherent to H‐aggregates was utilized for the exploration of water content detection. As an outcome, a high‐performance fluorescent filter paper was developed, enabling easy real‐time detection using a smartphone.

Correction to “Anticorrosion Agents for Carbon Steel in Acidic Environments: Synthesis and Quantum Chemical Analysis of New Schiff Base Compounds with Benzylidene”

Correction to “Anticorrosion Agents for Carbon Steel in Acidic Environments: Synthesis and Quantum Chemical Analysis of New Schiff Base Compounds with Benzylidene”

Theoretical and electrochemical analysis of halogenated salmphen-type dinuclear copper(II) complex: The influence of halogenated ligands on bandgap

The predictable control of energy levels in coordination polymer is an essential issue in molecular science. To explore a simple and feasible strategy for tuning the energy levels of Schiff base materials, the present work synthesized a novel halogen-substituted cofacial Schiff base compound, CuII2(2-Cl-Salmphen)2 (Cu-2-Cl-Salmphen), and the non-halogenated analogue CuII2(H-Salmphen)2 (Cu-H-Salmphen) was introduced for comparison. Experimental results show that the introduction of halogen atoms can effectively increase the absorbance and decrease the impedance of the compound. Further theoretical analyses revealed that the substitutional halogen atoms can not only enlarge the conjugation area but also change the electron density and the molecular orbital energy levels, thus enabling modulation of the bandgap values of the compounds. Besides, NCI studies have demonstrated that the substitution of halogens can form additional intermolecular interaction pathways, adjusting the interactions between adjacent molecules.

Synthesis Characterization and Biological Activity of 4-Methyl-benzene Sulfonohydrazide Derivatives

Background: A schiff base is generally a bi- or tri-dentate ligand capable of forming stable complexes with transition metals. Schiff base complexes have synthetic flexibilities and biological activity against various diseases. Objective: In the current study, Schiff bases compounds (PV1 - PV5) were synthesized from 4-methyl-1- benzene sulfonyl chloride. Subsequently, the synthesized products were analyzed for their antibacterial activity. Methods: Schiff base is a nitrogen analog with a carbonyl group. The reaction that results in the formation of new complexes involves the condensation of carbonyl compounds with an amine group. Furthermore, thin layer chromatography, FT-IR spectroscopy, and 1H-NMR were performed for product characterization. Results: All five complexes were successfully synthesized and some of the compounds demonstrated antibacterial, antifungal, anti-inflammatory and analgesic properties. Conclusion: The results confirmed the structure and presence of functional groups as per the scheme of synthesis. These synthesized compounds have the potential to treat the studied diseases and could be used as therapeutic candidates if further research is done.

Synthesis, Characterization, Molecular Docking Studies and Biological Evaluation of Thiazole Schiff Base Analogs

In this work, potentially safe few Schiff base compounds containing a thiazole moiety were synthesized and characterized. Three thiazole derivatives (2a-c) were successfully synthesized through a two-step reaction involving substituted benzaldehyde, thiosemicarbazide and 1,3-dichloroacetone. The elucidation of the synthesized compounds was accomplished by using spectral studies. Antimicrobial activities demonstrated that some compounds exhibited moderate effectiveness against microbes, compared to the standard antibiotic’s ceftriaxone and amphotericin B, using the disc diffusion technique. In the DPPH free radical scavenging assay, all compounds displayed promising antioxidant effectiveness. Moreover, the molecular docking studies showed that thiazole Schiff base analogs effectively bind to potential receptor binding sites.

Pyrimidine Schiff Bases: Synthesis, Structural Characterization and Recent Studies on Biological Activities.

Recently, 5-[(4-ethoxyphenyl)imino]methyl-N-(4-fluorophenyl)-6-methyl-2-phenylpyrimidin-4-amine has been synthesized, characterized, and evaluated for its antibacterial activity against Enterococcus faecalis in combination with antineoplastic activity against gastric adenocarcinoma. In this study, new 5-iminomethylpyrimidine compounds were synthesized which differ in the substituent(s) of the aromatic ring attached to the imine group. The structures of newly obtained pyrimidine Schiff bases were established by spectroscopy techniques (ESI-MS, FTIR and 1H NMR). To extend the current knowledge about the features responsible for the biological activity of the new 5-iminomethylpyrimidine derivatives, low-temperature single-crystal X-ray analyses were carried out. For all studied crystals, intramolecular N-H∙∙∙N hydrogen bonds and intermolecular C-H∙∙∙F interactions were observed and seemed to play an essential role in the formation of the structures. Simultaneously, their biological properties based on their cytotoxic features were compared with the activities of the Schiff base (III) published previously. Moreover, computational investigations, such as ADME prediction analysis and molecular docking, were also performed on the most active new Schiff base (compound 4b). These results were compared with the highest active compound III.

Synthesis and Therapeutic Potential of selected Schiff Bases: In vitro Antibacterial, Antioxidant, Antidiabetic, and Computational Studies

AbstractIn this study, three Schiff base compounds, (E)‐N‐(4‐bromophenyl)‐1‐(2‐nitrophenyl)methanimine (L1), (E)‐2‐((mesitylimino)methyl)phenol (L2), and (E)‐N‐(4‐bromophenyl)‐1‐(pyridin‐2‐yl)methanimine (L3), were synthesized and characterized by various spectroscopic techniques. The antibacterial activity of the compounds was evaluated against Gram‐positive and Gram‐negative bacteria, with L3 demonstrating the most significant activity. The compounds were also evaluated for their antioxidant activity using DPPH, FRAP, and NO scavenging assays. While the compounds exhibited concentration‐dependent scavenging of free radicals, their activity was not as significant as that of the reference, Trolox. Furthermore, L1–L3 were tested for their α‐amylase and α‐glucosidase inhibitory activity, with L1 showing the highest inhibitory activity among the three compounds. The DFT study showed that L1 is the most chemically reactive among the three compounds, having the lowest energy band gap value of 3.82 eV in acetonitrile, the experimental solvent. Molecular docking predicted that L1 and L2 have very strong inhibition equivalents to the standard drugs against bacteria and diabetes. All the compounds showed stronger inhibition against α‐glucosidase than acarbose, while only L1 and L2 exhibited stronger inhibition against α‐amylase than acarbose. It can be deduced that the theoretical studies corroborate well with the experimental, and compounds with the electron‐withdrawing group displayed better medicinal properties than their electron‐donating counterparts.

Schiff base flexible organic crystals toward multifunctional applications

AbstractThe emergence of flexible organic crystals changed the perception of molecular crystals that were regarded as brittle entities over a long period of time, and sparked a great interest in exploring mechanically compliant organic crystalline materials toward next‐generation smart materials during the past decade. Schiff base compounds are considered to be one of the most promising candidates for flexible organic crystals owing to their easy synthesis, high yield, stimuli responsiveness and good mechanical properties. This paper gives an overview of the recent development of Schiff base flexible organic crystals (including elastic organic crystals, plastic organic crystals, and flexible organic crystals integrating elasticity and plasticity) from serendipitous discovery to design strategies and versatile applications such as stimuli responses, optical waveguides, optoelectronic devices, biomimetic soft robots, and organic photonic integrated circuits. Notably, atomic force microscopy‐micromanipulation technique has been utilized to bring the multifunctional applications of flexible organic crystals from the macroscopic level to the microscopic world. Since understanding mechanical flexibility at the molecular level through crystal engineering can assist us to trace down the structural origin of mechanical properties, we focus on the packing structures of various Schiff base flexible organic crystals driven by non‐covalent intermolecular interactions and their close correlation with mechanical behaviors. We hope that the information given here will help in the design of novel flexible organic crystals combined with other unique properties, and promote further research into the area of mechanically compliant organic crystalline materials toward multifunctional applications.

Bioinspired Fluorine Labeling for 19F NMR-Based Plasma Amine Profiling.

Metabolite profiling serves as a powerful tool that advances our understanding of biological systems, disease mechanisms, and environmental interactions. In this study, we present an approach employing 19F-nuclear magnetic resonance (19F NMR) spectroscopy for plasma amine profiling. This method utilizes a highly efficient and reliable fluorine-labeling reagent, 3,5-difluorosalicylaldehyde, which effectively emulates pyridoxal phosphate, facilitating the formation of Schiff base compounds with primary amines. The fluorine labeling allows for distinct resolution of 19F NMR signals from amine mixtures, leading to precise identification and quantification of amine metabolites in human plasma. This advancement offers valuable tools for furthering metabolomics research.

Structural, electronic and optical properties of synthesized schiff base compound-validation with a computational method

Organic molecules have a profound impact on present-day technologies due to their structure, molecular interactions, ease of modification, and synthesis. The motivation of the present study is to synthesize a dielectric material at room temperature to accurately determine the optical properties the refractive index and dielectric constant and validate it using a computational method. Organic Schiff base compounds are synthesized in equimolar ratios with the host molecule Biphenyl-4-carboxaldehyde and guest molecules a family of distinct anilines using ultrasonication method. The advantages of this method over other conventional methods are a shorter reaction time, lower operating temperature, and easy work up with fewer amounts of solvents. Molecular aspects of synthesized Schiff bases were established by spectroscopic techniques i.e., IR, proton NMR and powdered x-ray diffraction methods showed that these results are consistent with the expected structure. Optical properties the refractive index and dielectric constant were recorded with a spectroscopic ellipsometer. Studies of computational methods provided optimized molecular structures with minimum energy with wavenumbers in agreement with recorded spectra. Quantum mechanical descriptors provide information on electronic and optical properties and help to visualize the corresponding changes in electron density using the Gaussian 16 package. The results of spectroscopic studies are in agreement with computed studies indicating that synthesized Schiff bases are active dielectric materials with major role of nitro compounds best suitable for optical and electronic properties with increased dielectric constant, refractive index and reduced energy.

Investigation of the molecular basis of halogenated Schiff base derivative by combined crystallographic and computational studies

Halogenated Schiff base derivatives are gaining more popularity in supramolecular chemistry due to the synergistic effect of hydrogen and halogen-based noncovalent interactions, which helps to design novel therapeutic materials. In this work, we have examined the nature of molecular interactions to investigate the structure-functional relationship of a halogen-based derivative. The FTIR, HRMS and NMR spectroscopic techniques confirmed the formation of the desired novel Schiff base compound. Further, crystal structure studies showed an infinite 1D supramolecular chain formed by type-I halogen…halogen interaction. The Hirshfeld surface and enrichment ratio analyses were performed to visualize and assess the role of diverse interactions involved in crystal packing. The QTAIM, NCI, LOL and ELF studies were conducted extensively to comprehend the strength of interaction constructed based on electron density distribution. The global and local reactive indices were determined using DFT studies to analyze the molecular properties of the compound. Antibacterial activity against MRSA bacteria was performed and showed a good zone of inhibition. The docking analysis was performed for 1mwt protein and validated. The in silico molecular docking studies of the halogenated Schiff base structure with the penicillin-binding protein showed a good docking affinity of −7.5 kcal/mol and supported by in vitro studies. The ligand binding stability within the protein’s active site was further demonstrated by molecular dynamics (MD) simulation studies for the Schiff base molecule. Communicated by Ramaswamy H. Sarma