Structural Characterization, DFT, Hirshfeld Surface Analysis and Antibacterial Activity of a Schiff Base Derived from Cyclohexanediamine

Nasaruddin, Nur Husnina; Ahmad, Shahrul Nizam; Sirat, Siti Syaida; Tan, Kong Wai; Zakaria, Nurul Aili; Bahron, Hadariah

doi:10.1016/j.molstruc.2021.130066

Cited by 16 publications

(4 citation statements)

References 38 publications

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“…As a result, the binding sites available for coordination with palladium and nickel are phenolic oxygen and azomethine nitrogen. The methyl protons signal was seen at 2.29 ppm in the spectrum of H 2 AD1Me which corresponds to the previously reported value . The signal was experiencing some shifting upon the complexation to the metal center.…”

Section: Resultssupporting

confidence: 86%

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Synthesis, Structural Characterization, Hirshfeld Surface Analysis, and Antibacterial Study of Pd(II) and Ni(II) Schiff Base Complexes Derived from Aliphatic Diamine

et al. 2022

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A Schiff base bearing two methyl substituents, namely, 6,6′-((1E,1′E)-((2,2-dimethylpropane-1,3-diyl) bis(azanylylidene)) bis(methanylylidene)) bis(2-methylphenol) [H2AD1Me] was synthesized and characterized through physicochemical and spectroscopic analyses. Then, the Schiff base was complexed with Pd(II) and Ni(II) to form [Pd(AD1Me)] and [Ni(AD1Me)], respectively. Both metal complexes were successfully obtained and characterized through several analyses, viz., melting point, elemental analysis, molar conductivity, magnetic susceptibility, FTIR, 1H NMR, UV–vis, and single crystal X-ray diffraction. A quantitative analysis of the intermolecular interactions in the crystal structures has been performed using Hirshfeld surface analysis. Both metal complexes were crystallized in a monoclinic crystal system with the space group of P21/c. Additionally, the deprotonated phenolic oxygen atom (O1/O2) and azomethine nitrogen atom (N1/N2) of the ligand chelate the Pd(II) and Ni(II) ions, forming a slightly distorted square-planar complex containing three six-membered rings encircling the metal core with dsp2 hybridization. The shift of ν(CN) to a higher frequency in FTIR by 26–28 cm–1 indicated that the complexation to Pd(II) and Ni(II) through the azomethine N was established. It was further supported through the shifting of the azomethine proton signal to higher or lower chemical shifts with Δδ = 0.43–1.15 ppm in 1H NMR. In addition, the shifting of the n−π*(CN) band in UV–vis spectra with Δλ = 24–40 nm indicated the involvement of azomethine nitrogen in the complexation. All the compounds showed no significant antibacterial activity against three bacterial strains, namely, Staphylococcus aureus subsp. aureus Rosenbach (ATCC 6538), Streptococcus mutans Clarke (ATCC 700,610), and Proteus vulgaris (ATCC 6380), as the percent growth inhibition calculated was less than 90%.

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Section: Resultssupporting

confidence: 86%

“…The methyl protons signal was seen at 2.29 ppm in the spectrum of H 2 AD1Me which corresponds to the previously reported value. 31 The signal was experiencing some shifting upon the complexation to the metal center.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Structural Characterization, Hirshfeld Surface Analysis, and Antibacterial Study of Pd(II) and Ni(II) Schiff Base Complexes Derived from Aliphatic Diamine

et al. 2022

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“… 29 We make a comparative study of some important 2D plots of MFIP and FPIN with some nitrogen–oxygen–halogen-rich compounds found from the literature. We choose compounds with the CSD reference code EQIDAL (CCDC number1410273), 30 ILUHIJ (CCDC number 2018498), 31 and JIPZUG (CCDC number 1884126) 32 for the 2D plots’ comparison with MFIP and FPIN . The 2D plots provide us the endowment of the inter-atomic contacts in percentage.…”

Section: Resultsmentioning

confidence: 99%

“…29 We make a comparative study of some important 2D plots of MFIP and FPIN with some nitrogen−oxygen−halogen-rich compounds found from the literature. We choose compounds with the CSD reference code EQIDAL (CCDC number1410273), 30 ILUHIJ (CCDC number 2018498), 31 and JIPZUG (CCDC The enrichment ratio 33 is computed for all the possible pairs of chemical species (X, X) and (X, Y) in MFIP and FPIN in order to determine the tendency of a pair of chemical species to form crystal packing interactions. The results are summarized in Table S2 for MFIP and Table S3 for FPIN.…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

et al. 2022

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This investigation is focused on the synthesis of two halo-functionalized crystalline Schiff base (imine) compounds: ( E )-2-methoxy-6-(((3-(trifluoromethyl)phenyl)imino)methyl)phenol ( MFIP ) and ( E )-1-(((2-fluorophenyl)imino)methyl)naphthalen-2-ol ( FPIN ) by the condensation reaction of substituted benzaldehydes and substituted aniline. The crystal structures of MFIP and FPIN were determined unambiguously by single-crystal X-ray diffraction (SC-XRD) studies. Intermolecular interactions and the role of fluorine atoms in the stabilization of the crystal packing are explored for both compounds using Hirshfeld surface analysis. Accompanied with experimental studies, quantum chemical calculations were also performed for comprehensive structure elucidation at the M06/6-311G(d,p) level of theory. A comparison of experimental and density functional theory results for geometrical parameters exhibited excellent agreement. Interestingly, Frontier molecular orbitals and natural bond orbital (NBO) findings revealed that intramolecular charge transfer and hyper-conjugation interactions had played a significant role to stabilize the molecules. Both compounds exhibited a relatively larger value of hardness with a smaller global softness, which, as proposed by the SC-XRD and NBO study, shows a higher stability. Nonlinear optical (NLO) findings showed that FPIN manifested a larger value of linear polarizability (< a > = 293.06 a.u.) and second-order hyperpolarizability (<γ> = 3.31 × 10 5 a.u.) than MFIP (< a > = 252.42 and <γ> = 2.08 × 10 5 a.u.) due to an extended conjugation. The above-mentioned findings of the entitled compounds may play a crucial role in NLO applications.

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Synthesis, crystal structure, and characterization of two new end-to-end 1D pseudohalide bridged manganese(III) complexes

Mandal,

Rizzoli,

Chakraborty

et al. 2024

Transit Met Chem

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Two new Manganese (III) Schiff base complexes MnL 2 N 3 (1) and MnL 2 NCS (2) where HL is 4-bromo-2-[(Z)-{[2-(thiophen-2-yl)ethyl]imino}methyl]phenol) were synthesized and characterized by UV-Vis. absorption spectra, FT-IR, photoluminescence (PL) emission spectra, TGA Analyses, and single-crystal Xray diffraction technique. Structural studies reveal that the metal sites in all complexes are sixcoordinated by two phenoxy oxygen and two imine nitrogen atoms of two moles of Schiff base ligand, HL. The geometry around the metal center is twisted octahedral geometry with a MnN 4 O 2 (for 1) and MnN 3 O 2 S (for 2) chromophore. Hirshfeld surfaces associated with 2D ngerprint plots have been used to analyze intermolecular interactions in crystal packing. Computational study using Density Functional Theory (DFT) has been done (for 1) to elucidate the structural information and energy gap calculation between HOMO & LUMO. Crystal packing of both complexes shows the interchain π π stacking interactions between one-dimensional chains.

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Structural Characterization, DFT, Hirshfeld Surface Analysis and Antibacterial Activity of a Schiff Base Derived from Cyclohexanediamine

Cited by 16 publications

References 38 publications

Synthesis, Structural Characterization, Hirshfeld Surface Analysis, and Antibacterial Study of Pd(II) and Ni(II) Schiff Base Complexes Derived from Aliphatic Diamine

Synthesis, Structural Characterization, Hirshfeld Surface Analysis, and Antibacterial Study of Pd(II) and Ni(II) Schiff Base Complexes Derived from Aliphatic Diamine

Synthesis of Crystalline Fluoro-Functionalized Imines, Single Crystal Investigation, Hirshfeld Surface Analysis, and Theoretical Exploration

Synthesis, crystal structure, and characterization of two new end-to-end 1D pseudohalide bridged manganese(III) complexes

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