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Synthesis, crystal structure, Hirshfeld surface analysis, energy frameworks and computational studies of Schiff base derivative.

ABSTRACT: The compound (E)-ethyl 3-(2-(2,4-dinitrophenyl)hydrazono)butanoate (3) was synthesised and crystallized using ethanol as a solvent. The compound was characterized by ¹H NMR, and single crystal X-ray diffraction. The compound crystallizes in the monoclinic crystal system with the space group P2₁/c. The intermolecular interactions and the interaction energies responsible for the stabilization of the molecules were determined by Hirshfeld surface analysis and energy framework calculations. The structure of the compound was optimized by Density Functional Theory calculations and HOMO-LUMO energy gap was calculated. The non-covalent interactions were revealed by reduced density gradient analysis. The Mulliken atomic charges and natural atomic charges were calculated by density functional theory calculations. The reactive sites present in the molecule are shown by molecular electrostatic potential map. The inter and intra molecular charge transfer were investigated by NBO analysis.

SUBMITTER: Chandini KM

PROVIDER: S-EPMC9434054 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

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Synthesis, crystal structure, Hirshfeld surface analysis, energy frameworks and computational studies of Schiff base derivative.

Chandini K M KM Nagesh Khadri M J MJ Amoghavarsha N N Sridhar M A MA Khanum Shaukath Ara SA

Heliyon 20220807 8

The compound (E)-ethyl 3-(2-(2,4-dinitrophenyl)hydrazono)butanoate (3) was synthesised and crystallized using ethanol as a solvent. The compound was characterized by 1H NMR, and single crystal X-ray diffraction. The compound crystallizes in the monoclinic crystal system with the space group P21/c. The intermolecular interactions and the interaction energies responsible for the stabilization of the molecules were determined by Hirshfeld surface analysis and energy fra ...[more]

PMID: 36061005

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Project description:Eight Schiff bases, synthesized by the reaction of 4-aminoantipyrine with different cinnamaldehydes, were studied in the solid state by using vibrational spectroscopy (IR) and X-ray diffraction techniques. The analysis was extended to the solution phase through ultraviolet-vis, fluorescence spectroscopy, and cyclic voltammetry. Finally, the crystal structures of four compounds (3b, 3d, 3g, and 3h) were determined and studied. In addition to the experimental study, theoretical calculations using the semiempirical method PM6/ZDO were performed to understand better the compound's molecular properties, UV-vis, and infrared spectra. The primary difference is the angular conformation of the terminal phenyl rings around the corresponding linking C-N and C-C σ-bonds. Furthermore, as a result of extended bonding, the > C=N- azomethine group-containing Cpyr-N=(CH)-(CR)=(CH)-Cbz chain (with R=H for 3b, 3d, and 3h, and R=CH3 for 3g) is planar, nearly coplanar, with the mean plane of the pyrazole ring. Hirshfeld surface (HS) analysis was used to investigate the crystal packing and intermolecular interactions, which revealed that intermolecular C-H···O and C-H···N hydrogen bonds, π···π stacking, and C-H···π and C=O···π interactions stabilize the compounds. The energy contributions to the lattice energies of potential hydrogen bonds were primarily dispersive and repulsive. All derivatives were tested in vitro on LPS-stimulated mouse macrophages to assess their ability to suppress the LPS-induced inflammatory responses. Only a slight reduction in the level of NO production was found in activated macrophages treated with 3h. Additionally, the derivatives were tested for antimicrobial activity against several clinical bacteria and fungi strains, including three biofilm-forming microorganisms. Nevertheless, only Schiff base 3f showed interesting antibacterial activities with minimum inhibitory concentration (MIC) values as low as 15.6 μM against Enterobacter gergoviae. On the other hand, Schiff base 3f and, to a lesser extent, 3b and 3h showed antifungal activity against clinical isolates of Candida. The lowest MIC value was for 3f against Candida albicans (15.6 μM). It is interesting to note that the same Schiff bases exhibit the highest activity in both biological evaluations.

Project description:The inhibitory effect of di-imine-SB namely ((N1Z, N4E)-N1, N4-bis (4 (dimethylamino) benzylidene) butane 1,4-diamine) on X65-steel in 1 M HCl has been investigated experimentally and theoretically. The electrochemical impedance spectroscopy (EIS), potentiodynamic polarization (PDP), and weight loss outcomes display the anticorrosion properties of "di-imine- SB". The inhibitory efficiency exceeds 90% at the optimal concentration of 1 × 10-3 M "di-imine- SB". The metal surface was examined further using scanning electron microscope (SEM) and energy dispersive X-ray (EDX). The effectiveness of the di-imine-SB is returned into its adsorption on X65-steel surface and found in agreement with Langmuir adsorption isotherm. According to the standard Gibbs free energy of adsorption [Formula: see text], di-imine-SB adsorption tends to be chemical rather than physical, it increases the activation energy ([Formula: see text]) of metal dissolution reaction and makes it hard to occur. The PDP data suggested anodic and cathodic type of the di-imine-SB inhibitor. Meanwhile, increasing the resistance of X65-steel to 301 Ω cm2 after adding 1 mM of di-imine-SB confirms its protective effect. Whereas, the positive value of the fraction of electron transference (ΔN, 0.746), confirms the affinity of di-imine-SB to share electrons to the partially filed 3d-orbital of Fe forming strong protective film over X65-steel surface. Aided by Monte Carlo (MC) simulation, the calculated adsorption energy (Eads) suggests excessive adsorption affinity of di-imine-SB on metal surface over the corrosive chlorides and hydronium ions. A good correlation between the theoretical hypothesis and the experimental inhibition efficiency has been achieved. The comparative study showed the superior of the di-imine-SB as potential corrosion inhibitor compared with those reported before. Finally, global reactivity descriptors; electron affinity (A), ionization potential (I), electronegativity (χ), dipole moment (µ), global hardness ([Formula: see text]), electrophilicity index and, Fukui indices were also calculated and found well correlated to the reactivity of di-imine-SB.

Project description:Three Schiff bases were synthesised by the condensation reaction between 2-napthaldehyde and aromatic amines to afford (E)-N-mesityl-1-(naphthalen-2-yl)methanimine (L1), (E)-N-(2,6-dimethylphenyl)-1-(naphthalen-2-yl)methanimine (L2) and (E)-N-(2,6-diisopropylphenyl)-1-(naphthalen-2-yl)methanimine (L3). The synthesised compounds were characterised using UV-visible, NMR (13C & 1H), and Fourier transform infrared spectroscopic methods while their purity was ascertained by elemental analysis. Structural analysis revealed that the naphthalene ring is almost coplanar with the imine functional group as evident by C1-C10-C11-N1 torsion angles of 176.4(2)° and 179.4(1)° in L2 and L3, respectively. Of all the various intermolecular contacts, H⋯H interactions contributed mostly towards the Hirshfeld surfaces of both L2 (58.7 %) and L3 (69.7 %). Quantum chemical descriptors of L1 - L3 were determined using Density Functional Theory (DFT) and the results obtained showed that the energy band gap (ΔE) for L1, L2 and L3 are 3.872, 4.023 and 4.004 eV respectively. The antidiabetic potential of the three compounds were studied using α-amylase and α-glucosidase assay. Compound L1 showed very promising antidiabetic activities with IC50 values of 58.85 μg/mL and 57.60 μg/mL while the reference drug (Acarbose) had 405.84 μg/mL and 35.69 μg/mL for α-amylase and α-glucosidase respectively. In-silico studies showed that L1 docking score as well as binding energies are higher than that of acarbose, which are recognized inhibitors of α-amylase together with α-glucosidase. Further insight from the RMSF, RMSD and RoG analysis predicted that, throughout the simulation L1 showcased evident influence on the structural stability of α-amylase. The antioxidant potential of the compounds was carried out using nitric oxide (NO), ferric reducing ability power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays. The compounds exhibited good to fairly antioxidant properties with L1 as well as L3 having IC50 values of 70.91 and 91.21 μg/mL respectively for NO scavenging activities assay, which comparatively outshined acarbose (reference drug) with IC50 value of 109.95 μg/mL. Pharmacology and pharmacokinetics approximations of L1 - L3 showed minimal violation of Lipinski's Ro5 and this projects them to be less toxic and orally bioavailable as potential templates for the design of therapeutics with antioxidant and antidiabetic activities.

Dataset Information

Synthesis, crystal structure, Hirshfeld surface analysis, energy frameworks and computational studies of Schiff base derivative.

Publications

Synthesis, crystal structure, Hirshfeld surface analysis, energy frameworks and computational studies of Schiff base derivative.

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