Supramolecular assembly in designing co-crystals of fumaric acid and pyrimidine/picolinate derivatives

Kansız, Sevgi; Azam, Mohammad; Dege, Necmi; Ermiş, Nihal; Al‐Resayes, Saud I.; Alam, Mahboob

doi:10.1080/17518253.2022.2130016

Cited by 5 publications

(3 citation statements)

References 45 publications

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“…The input files were generated using Chemdraw, and the output data was visualized using Gauss View 6.0 , It is essential to utilize the provided equations precisely to obtain quantum chemical reactivity parameters. Density functional theory (DFT) calculations using B3LYP utilizing the LANL2DZ basis set were used to accomplish the whole compound optimization as shown in Figure , followed by analyses of the NBO, Fukui index, FMO, MEP, and vibrational frequencies. − The band energy gap information was obtained from the highest occupied and lowest unoccupied molecular orbital representations (HOMO–LUMO). Global reactivity descriptors and thermodynamical parameters for different temperatures were computed and reported to expose the qualities of the PA with FP, CP, BP, and IP compounds.…”

Section: Methodsmentioning

confidence: 99%

Ternary Mixture of Pentanamide in Solvent Analogy with Halogenated Phenol: Experimental, Theoretical, andIn SilicoBiological Studies

Basha,

Ali Khan,

Kubaib

et al. 2023

ACS Omega

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This research describes the preparation of mixtures of new halogen-substituted phenol derivatives and their effects due to linkages with a fatty amide (pentanamide). The molecules were optimized using DFT, and the vibrational and electronic analysis was done subsequently. The energies of frontier molecular orbitals (FMOs) were used to estimate the global chemical reactivity parameters as we suggest that hydrogen-bonded networks may have contributed to the stability and reactivity of the compound. In addition to the experimental investigation, dielectric parameters were calculated. Fukui functions were analyzed to study the chemical reactivity. To get insight into interactions of σ → π* orbitals, natural bond orbital calculations were done. Additionally, surface analysis of the MEP and Hirshfeld charges were performed at the equivalent DFT levels. The research also indicated that both (interaction region indicator) IRI and (electron delocalize range) EDR would proficiently identify chemical-bonding and weak interaction regions, providing a significant advantage in exploring diverse chemical systems and reactions. This indicated that compounds could diffuse through noncovalent interactions, including intramolecular hydrogen bonding. Dielectric relaxation studies taken at five distinct molar ratios identified significant dielectric properties such as ε′, ε″, ε0, and ε∞. The PA with FP, CP, BP, and IP molecules has potential antiviral and antioxidant benefits for carbonic anhydrase, with favorable drug-like features and diverse biological benefits. Pharmacological effects were forecasted using the PASS server, and these molecules exhibited favorable pharmacokinetic properties.

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Section: Methodsmentioning

confidence: 99%

Ternary Mixture of Pentanamide in Solvent Analogy with Halogenated Phenol: Experimental, Theoretical, andIn SilicoBiological Studies

Basha,

Ali Khan,

Kubaib

et al. 2023

ACS Omega

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“…The Natural Bond Orbital (NBO) [21] was calculated at B3LYP level using the basis set 6-311++ G(d,p). This analysis was done to give clear evidence of stabilization originating from hyper conjugation of various intramolecular interactions [22][23][24][25]. To get insight on the intermolecular H-bonding, the most important AIM topological parameters at bond critical points (BCP) of O-H and O•••H contacts have been calculated by using the Multiwfn software [26].…”

Section: Computational Detailsmentioning

confidence: 99%

Vibrational Spectroscopies, Global Reactivity, Molecular Docking, Thermodynamic Properties and Linear and Nonlinear Optical Parameters of Monohydrate Arsenate Salt of 4-Aminopyridine

et al. 2023

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In this work, a structural and electronic properties of a novel organic arsenate template by 4-aminopyridine, with the general formula (C 5 H 7 N 2 )(C 5 H 8 N 2 )[AsO 4 ]·H 2 O ((4-APH)(4-APH 2 )[AsO 4 ]·H 2 O) have been presented. The density functional theory (DFT) along with B3LYP hybrid functional is employed. The optimized structure was found to be in well consistent with the X-ray diffraction geometry. The examination of the vibrational spectrum was correlated by DFT calculation using the unit cell parameters obtained from the experiment data. Besides, the thermodynamic functions (heat capacity, entropy, enthalpy) from spectroscopic data by statistical methods were obtained for the range of temperature 100–1000 K. In addition, the molecular orbital calculations such as Natural Bond Orbitals (NBOs), AIM approach, HOMO–LUMO energy gap, NLO characteristic and Hirshfeld surface analysis were also performed with the same level of DFT. Electronic stability of the compound arising from hyper conjugative interactions and charge delocalization were also investigated based on the natural bond orbital (NBO) analysis. Molecular docking studies were also conducted as part of this study. The theoretical results showed an excellent agreement with the experimental values. Supplementary Information The online version contains supplementary material available at 10.1007/s42250-023-00620-8.

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“…However, aliphatic acyclic compounds which constitute a large portion of the dictionary of organic compounds are not well explored, except for some examples, especially, in the pharmaceutical co-crystals. To name a few, some of the dicarboxylic acids − (fumaric acid, succinic acid, adipic acid, etc.) belong to GRAS (generally recognized as safe), and a few other tri- and tetracarboxylic acid-substituted compounds like aconitic acid (a tricarboxylic entity), − tetracarboxylic acid (butane-1,2,3,4-tetracarboxylic acid), , and so forth are well documented, as retrieved from the Cambridge Structural Database (CSD).…”

Section: Introductionmentioning

confidence: 99%

Systematic Exploration of Structural Topologies in Hydrogen-Bonded Supramolecular Assemblies of Citric Acid with Different Heterocyclic Compounds

Easmin

Pedireddi

2023

ACS Omega

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Hydrogen-bonded supramolecular assemblies of citric acid, CA, with some heterocyclic compounds (N-donor and N-oxide)acridine (acr), phenazine (phenz), 1,10-phenanthroline (110phen), 1,7-phenanthroline (17phen), 4,7-phenanthroline (47phen), 1,4-diazabicyclo[2.2.2]octane (dabco), and 4,4′-bipyridyl-N,N′-dioxide (bpydo)have been reported. Among these, only the N-donors phenz and N-oxide (bpydo) form neutral co-crystals, while the others form salts owing to the deprotonation of −COOH. Thus, depending on the nature of the aggregate (salt/co-crystal), recognition between the co-formers is established through O–H···N/N+–H···O/N+H···O– heteromeric hydrogen bonding. Additionally, CA molecules establish homomeric interactions mediated by O–H···O hydrogen bonds. Moreover, CA forms a cyclic network with the co-formers or on its own, with a noteworthy feature of formation of host–guest networks in the assemblies with acr and phenz (solvated). In the assembly of acr, the CA molecules form a host network and captivate acr molecules as guest species, while in the case of phenz assembly, both the co-formers together encapsulate the solvent in the channels. However, the observed cyclic networks in the other structures form three-dimensional topologies in the form of ladders, a sandwich, lamellar layers, and interpenetrated networks. The structural features of the ensembles are evaluated unequivocally by the single-crystal X-ray diffraction method, while the homogeneity and phase purity are evaluated by using the powder X-ray diffraction method and differential scanning calorimetry. Further, conformational analysis of CA molecules reveals three types of conformationsT-shape (type I), syn–anti (type II), and syn (type III) as also observed in the literature for other CA co-crystals. In addition, the strength of the intermolecular interactions is quantified by performing Hirshfeld analysis.

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Supramolecular assembly in designing co-crystals of fumaric acid and pyrimidine/picolinate derivatives

Cited by 5 publications

References 45 publications

Ternary Mixture of Pentanamide in Solvent Analogy with Halogenated Phenol: Experimental, Theoretical, andIn SilicoBiological Studies

Ternary Mixture of Pentanamide in Solvent Analogy with Halogenated Phenol: Experimental, Theoretical, andIn SilicoBiological Studies

Vibrational Spectroscopies, Global Reactivity, Molecular Docking, Thermodynamic Properties and Linear and Nonlinear Optical Parameters of Monohydrate Arsenate Salt of 4-Aminopyridine

Systematic Exploration of Structural Topologies in Hydrogen-Bonded Supramolecular Assemblies of Citric Acid with Different Heterocyclic Compounds

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