Charge Transfer Complexes of Ketotifen with 2,3-Dichloro-5,6-dicyano-p-benzoquinone and 7,7,8,8-Tetracyanoquodimethane: Spectroscopic Characterization Studies

Mostafa, Gamal A. E.; Bakheit, Ahmed H.; AlMasoud, Najla; AlRabiah, Haitham

doi:10.3390/molecules26072039

Cited by 8 publications

(6 citation statements)

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“…Understanding these electrostatic interactions is essential for comprehending the behavior and function of the CBP-TPB complex. Further studies focusing on other molecular properties, such as intermolecular interactions and atomic charge distributions, could provide a more comprehensive understanding of the complex and its potential applications [45,46].…”

Section: Molecular Electrostatic Nature Of Interactions-mespmentioning

confidence: 99%

Synthesis, X-ray Crystal Structure, and Computational Characterization of Tetraphenylborate, 3-(5H-Dibenzo[a,d] cyclohepten-5-ylidene)-N, N-Dimethyl-1-propanamine

et al. 2023

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A cyclobenzaprine-tetraphenylborate (CBP-TPB) complex was synthesized, achieving a 78% yield through an anion exchange reaction. The white crystals of the complex were formed in acetonitrile and characterized using a variety of spectroscopic and analytical techniques, including ultraviolet, infrared, mass, elemental, and nuclear magnetic resonance (NMR) spectroscopy, as well as X-ray crystallography. The study employed a comprehensive approach to investigate the structural properties, stability, and behavior of the CBP-TPB complex. The use of crystallographic analysis, Hirshfeld surface analysis, quantum theory of atoms in molecules, noncovalent interaction reduced density gradient, global reactivity descriptors, frontier molecular orbitals, molecular electrostatic potential, and ultraviolet-visible spectroscopy provided valuable insights into the complex’s molecular geometries, supramolecular features, and intermolecular interactions. These findings contribute to a better understanding of the CBP-TPB complex’s potential applications in fields such as pharmaceuticals and materials science and emphasize the importance of combining theoretical predictions and experimental measurements in understanding molecular properties. The study also demonstrated the potential of density functional theory-based computational methods for predicting NMR spectroscopic parameters.

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Section: Molecular Electrostatic Nature Of Interactions-mespmentioning

confidence: 99%

Synthesis, X-ray Crystal Structure, and Computational Characterization of Tetraphenylborate, 3-(5H-Dibenzo[a,d] cyclohepten-5-ylidene)-N, N-Dimethyl-1-propanamine

et al. 2023

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“…For instance, regions identified as nucleophilic in the MEP analysis might correlate with areas where the HOMO is densely populated, while electrophilic regions might align with areas dominated by the LUMO. Together, the MEP and FMO analyses can elucidate potential bond interactions, further refining the understanding of the molecule's interactions in different chemical environments [29,43,44].…”

Section: Electrostatic Potential Representation Of the Molecule (Mep)mentioning

confidence: 99%

Integrated Structural, Functional, and ADMET Analysis of 2-Methoxy-4,6-diphenylnicotinonitrile: The Convergence of X-ray Diffraction, Molecular Docking, Dynamic Simulations, and Advanced Computational Insights

Bakheit,

Alkahtani

2023

Molecules

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This study systematically investigates the molecular structure and electronic properties of 2-methoxy-4,6-diphenylnicotinonitrile, employing X-ray diffraction (XRD) and sophisticated computational methodologies. XRD findings validate the compound’s orthorhombic crystallization in the P21212 space group, composed of a pyridine core flanked by two phenyl rings. Utilizing the three-dimensional Hirshfeld surface, the research decodes the molecule’s spatial attributes, further supported by exhaustive statistical assessments. Key interactions, such as π–π stacking and H⋯X contacts, are spotlighted, underscoring their role in the crystal’s inherent stability and characteristics. Energy framework computations and density functional theory (DFT) analyses elucidate the prevailing forces in the crystal and reveal geometric optimization facets and molecular reactivity descriptors. Emphasis is given to the exploration of frontier molecular orbitals (FMOs), aromaticity, and π–π stacking capacities. The research culminates in distinguishing electron density distributions, aromatic nuances, and potential reactivity hotspots, providing a holistic view of the compound’s structural and electronic landscape. Concurrently, molecular docking investigates its interaction with the lipoprotein-associated phospholipase A2 protein. Notably, the compound showcases significant interactions with the protein’s active site. Molecular dynamics simulations reveal the compound’s influence on protein stability and flexibility. Although the molecule exhibits strong inhibitory potential against Lp-PLA2, its drug development prospects face challenges related to solubility and interactions with drug transport proteins.

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“…There are numerous p -benzoquinone derivatives that are extensively utilized as π acceptors in the production of different CT complexes involved in energy storage that play a crucial role in biological activity. Colored reagents are essential for the quantitative investigation of several medicinal compounds that can act as electron donors [ 5 ]. In general, charge transfer includes the transfer of electrons from the donor molecule to the benzoquinone molecule as acceptors, resulting in the formation of a benzoquinone radical anion, which then forms a free radical ion pair or ion pair [ 5 , 6 ].…”

Section: Introductionmentioning

confidence: 99%

“…Colored reagents are essential for the quantitative investigation of several medicinal compounds that can act as electron donors [ 5 ]. In general, charge transfer includes the transfer of electrons from the donor molecule to the benzoquinone molecule as acceptors, resulting in the formation of a benzoquinone radical anion, which then forms a free radical ion pair or ion pair [ 5 , 6 ]. 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) ( Figure 1 B) and Chloranilic acid (CHA) ( Figure 1 C) are well-known benzoquinone derivatives that act as powerful π acceptors in the complexation of anion radicals.…”

Section: Introductionmentioning

confidence: 99%

“…2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) ( Figure 1 B) and Chloranilic acid (CHA) ( Figure 1 C) are well-known benzoquinone derivatives that act as powerful π acceptors in the complexation of anion radicals. Many donor bases are produced in stable free-ion pair complexes as a result of their work [ 5 , 6 , 7 ]. The binding of that free radical ion or ion pair is dependent on chemical interactions, which are mostly non-covalent [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

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Thermodynamic and Computational (DFT) Study of Non-Covalent Interaction Mechanisms of Charge Transfer Complex of Linagliptin with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and Chloranilic acid (CHA)

2022

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This study describes the non-covalent interactions of the charge transfer complex (CT), which was responsible for the synthesis of Linagliptin (LNG) with 2, 3-Dichloro-5, 6-Dicyano-1, 4-benzoquinone (DDQ), or with chloranilic acid (CHA) complexes in acetonitrile (MeCN) at temperatures of (25 ± 2 °C). Then, a UV–Vis spectrophotometer was utilized to identify Linagliptin (LNG) from these complexes. For the quantitative measurement of Linagliptin in bulk form, UV–Vis techniques have been developed and validated in accordance with ICH criteria for several aspects, including selectivity, linearity, accuracy, precision, LOD, LOQ, and robustness. The optimization of the complex synthesis was based on solvent polarization; the ratio of molecules in complexes; the association constant; and Gibbs energy (ΔG°). The experimental work is supported by the computational investigation of the complexes utilizing density functional theory as well as (QTAIM); (NCI) index; and (RDG). According to the optimized conditions, Beer’s law was observed between 2.5–100 and 5–100 µM with correlation coefficients of 1.9997 and 1.9998 for LGN-DDQ and LGN-CHA complexes, respectively. For LGN-DDQ and LGN-CHA complexes, the LOD and LOQ were (1.0844 and 1.4406 μM) and (3.2861 and 4.3655 μM), respectively. The approach was successfully used to measure LGN in its bulk form with high precision and accuracy.

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Charge Transfer Complexes of Ketotifen with 2,3-Dichloro-5,6-dicyano-p-benzoquinone and 7,7,8,8-Tetracyanoquodimethane: Spectroscopic Characterization Studies

Cited by 8 publications

References 36 publications

Synthesis, X-ray Crystal Structure, and Computational Characterization of Tetraphenylborate, 3-(5H-Dibenzo[a,d] cyclohepten-5-ylidene)-N, N-Dimethyl-1-propanamine

Synthesis, X-ray Crystal Structure, and Computational Characterization of Tetraphenylborate, 3-(5H-Dibenzo[a,d] cyclohepten-5-ylidene)-N, N-Dimethyl-1-propanamine

Integrated Structural, Functional, and ADMET Analysis of 2-Methoxy-4,6-diphenylnicotinonitrile: The Convergence of X-ray Diffraction, Molecular Docking, Dynamic Simulations, and Advanced Computational Insights

Thermodynamic and Computational (DFT) Study of Non-Covalent Interaction Mechanisms of Charge Transfer Complex of Linagliptin with 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and Chloranilic acid (CHA)

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