Synthesis, structural studies, Hirshfeld surface analysis, and molecular docking studies of a thiophene-based Schiff base compound

Kansız, Sevgi; Azam, Mohammad; Basılı, Taşkın; Meral, Seher; Aktas, Feyzi Alkim; Yeşilbağ, Semanur; Kim, Min; Ağar, Ayşen Alaman; Dege, Necmi

doi:10.1016/j.molstruc.2022.133477

Cited by 32 publications

(3 citation statements)

References 40 publications

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“…Electrophilic attacks involve electron-seeking species (electrophiles), while nucleophilic attacks involve electrondonating species (nucleophiles). These attacks play a crucial role in chemical reactions, with electrophiles and nucleophiles interacting to form new chemical bonds [18][19][20][21].…”

Section: B the Molecular Electrostatic Potentialsmentioning

confidence: 99%

Quantum Chemical Insights into 2-[2-(Benzyloxy)benzylidene] malononitrile: DFT Analysis, MEP Surface Mapping, and HOMO-LUMO Energies

2023

Proceeding Book of 4th International Conference on Engineering and Applied Natural Sciences ICEANS 2023

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Malononitriles and their benzylidene derivatives stand out as a versatile class of organic compounds acclaimed for their wide-ranging pharmacological activities. Their crucial involvement in condensation reactions, driven by the reactivity of the active nucleophilic methylene group, holds profound significance across diverse industries, including medicine, industry, and agriculture. As computational methods have become integral for unraveling molecular-level behavior, this study delves into the theoretical calculations of the compound 2-[2-(benzyloxy)benzylidene] malononitrile. Utilizing Density Functional Theory (DFT) and Lee-Yang-Parr (LYP) with the B3LYP model, a 3-parameter Becke mixed model with correlation energy, and the 6-311G(d,p) basis set, the theoretical framework unfolds. The optimization process seeks the molecular system's solution, bringing it closest to the real system and reaching its most stable state. Post-optimization, the electrophilic and nucleophilic properties, derived from energy, are unveiled through local and global chemical activity calculations. Global chemical activity data, integrating hardness and softness parameters derived from the HOMO and LUMO energies (the primary molecular orbitals), offer insights into the overall reactivity. Concurrently, local chemical activity data, obtained through molecular electrostatic potential map analysis, provide a nuanced understanding of electrophilic and nucleophilic tendencies within the structure. This comprehensive computational approach elucidates the molecular behavior of 2-[2-(benzyloxy)benzylidene] malononitrile, contributing valuable insights for potential applications in various fields.

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Section: B the Molecular Electrostatic Potentialsmentioning

confidence: 99%

Quantum Chemical Insights into 2-[2-(Benzyloxy)benzylidene] malononitrile: DFT Analysis, MEP Surface Mapping, and HOMO-LUMO Energies

2023

Proceeding Book of 4th International Conference on Engineering and Applied Natural Sciences ICEANS 2023

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“…Hirshfeld surface analysis [15,16] has emerged as a widely employed and influential technique in various scientific domains, including materials science, crystal engineering, and computational chemistry [17][18][19][20]. It serves as a robust tool, offering invaluable insights into the intricate world of intermolecular interactions and the packing arrangements within molecular crystals.…”

Section: B the Hirshfeld Surface Analysismentioning

confidence: 99%

Structural Analysis, Surface Examination, and Voids Characterization of a Copper (II) Complex Featuring Dual Picolinic Acid Ligands

2023

Proceeding Book of 2nd International Conference on Recent Academic Studies ICRAS 2023

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Picolinic acid, or 2-pyridinecarboxylic acid, is a heterocyclic organic compound characterized by the chemical formula C6H5NO2. As a derivative of pyridine, it belongs to the carboxylic acid family and holds significant functional importance in various chemical reactions, coordination chemistry, and as a fundamental building block for synthesizing complex compounds. Picolinic acid, doubling as a versatile ligand in coordination chemistry, finds widespread applications in pharmaceuticals, agricultural chemicals, and materials science. This study delves into the crystal structure analysis of a copper complex featuring the picolinic acid ligand, denoted as C12H9Br2N6CuO4. The Cu(II) complex crystallizes in the triclinic space group P-1, with a single molecule housed within the asymmetric unit. Within the crystal lattice, the pyridine rings assume a dihedral angle of 66.95 (3)°. Molecular cohesion is achieved through intermolecular C-H•••O and C-H•••Br hydrogen bonds, leading to the formation of layered structures parallel to the bc plane. Additionally, aromatic π-π stacking interactions further bolster the packing arrangement of the title compound. To garner deeper insights, Hirshfeld surface analysis was employed to investigate the spatial distribution of atoms capable of forming hydrogen bonds, coupled with a quantitative assessment of these interactions within the Cu(II) complex. The results underscore the paramount role of specific interactions in shaping the crystal packing. Particularly noteworthy are contributions from O•••H interactions (32.3%), H•••H contacts (20.2%), Br•••H associations (11.8%), and C•••H connections (6.5%). The study also includes an analysis of voids within the crystal structure, providing a comprehensive characterization of this intriguing copper complex.

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“…[12][13][14] Additionally, the Schiff base's geometric cavity can govern how the host and visitor interact and its lipophilicity also stimulates synthetic flexibility and selectivity for particles. [15][16][17] To produce large molecular weight conjugated Schiff base polymers, a significant amount of work has been done in recent years. However, the insolubility of most conjugated aromatic poly (Schiff bases) in common organic solvents has been a significant barrier to characterizing and producing these compounds with high thermal stability.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Anticancer Potency of Branched Poly (p‐Hydroxy Styrene) Schiff‐Bases

Kenawy

El-Khalafy

Abosharaf

et al. 2023

Macromolecular Bioscience

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A significant issue in cancer biology is finding anticancer therapies that effectively kill cancer cells. Through the use of several aldehydes, Schiff bases based on branched poly (p‐hydroxy styrene) are created. The branched polymer is first chloroacetylated, then aminated with 1,4‐phenylenediamine, and finally, aldehydes are reacted with the aminated polymer to produce the Schiff base compounds. Through the utilization of FTIR, TGA, XRD, NMR, and elemental analysis, all synthesized Schiff‐bases are identified and characterized. Further, the antineoplastic potential of all Schiff bases is evaluated against different cancer cell lines. The results gained from this study indicate that the Schiff base polymers have cytotoxic power against cancer cells depending on cancer cell type and this antiproliferation potency is dose‐concentration dependent. Importantly, the prepared S1 Schiff‐base polymer shows potent cytotoxicity and is able to trigger the apoptosis and reactive oxygen species (ROS) in MCF‐7 cells. Further, it downregulates VEGFR protein expression. The Schiff base polymers would have extensive applications in the biological disciplines.

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Synthesis, structural studies, Hirshfeld surface analysis, and molecular docking studies of a thiophene-based Schiff base compound

Cited by 32 publications

References 40 publications

Quantum Chemical Insights into 2-[2-(Benzyloxy)benzylidene] malononitrile: DFT Analysis, MEP Surface Mapping, and HOMO-LUMO Energies

Quantum Chemical Insights into 2-[2-(Benzyloxy)benzylidene] malononitrile: DFT Analysis, MEP Surface Mapping, and HOMO-LUMO Energies

Structural Analysis, Surface Examination, and Voids Characterization of a Copper (II) Complex Featuring Dual Picolinic Acid Ligands

Synthesis, Characterization, and Anticancer Potency of Branched Poly (p‐Hydroxy Styrene) Schiff‐Bases

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