Exploring weak intermolecular interactions in two bis-1,3,4-oxadiazoles derivatives: A combined X-ray diffraction, Hirshfeld surface analysis and theoretical studies

Ahmed, Muhammad Naeem; Nadeem, Komal; Andleeb, Hina; Sheikhi, Masoome; Majeed, Zahid; Shah, Syed Wadood Ali; Tahir, Muhammad Nawaz; Rocha, Mariana; Gil, Diego M.

doi:10.1016/j.molstruc.2021.130030

Cited by 8 publications

(3 citation statements)

References 54 publications

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“…Only recently, the involvement of oxadiazole core in stacking-like intermolecular interactions was demonstrated based on structural and theoretical data of two 1,3,4-oxadiazole derivatives [ 50 ]. The performed docking studies of binding these compounds to recombinant human acetylcholinesterase also demonstrated the possibility of stacking interactions between oxadiazole ring and aryl moiety of tyrosine, tryptophan, and phenylalanine in the binding site.…”

Section: Introductionmentioning

confidence: 99%

π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

et al. 2021

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A series of N-pyridyl ureas bearing 1,2,4- (1a, 2a, and 3a) and 1,3,4-oxadiazole moiety (1b, 2b, 3b) was prepared and characterized by HRMS, 1H and 13C NMR spectroscopy, as well as X-ray diffraction. The inspection of the crystal structures of (1–3)a,b and the Hirshfeld surface analysis made possible the recognition of the (oxadiazole)···(pyridine) and (oxadiazole)···(oxadiazole) interactions. The presence of these interactions was confirmed theoretically by DFT calculations, including NCI analysis for experimentally determined crystal structures as well as QTAIM analysis for optimized equilibrium structures. The preformed database survey allowed the verification of additional examples of relevant (oxadiazole)···π interactions both in Cambridge Structural Database and in Protein Data Bank, including the cocrystal of commercial anti-HIV drug Raltegravir.

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Section: Introductionmentioning

confidence: 99%

π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

et al. 2021

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“…They are being used for massive crystal structure generation and possible prediction . The Hirshfeld surface is created based on the electron distribution of a molecule, and it has been calculated as the sum of spherical atom electron densities . It was used to quantify the contribution of intermolecular interactions that stabilize the crystal packing and to understand the nature of intermolecular interactions .…”

Section: Introductionmentioning

confidence: 99%

“… 16 The Hirshfeld surface is created based on the electron distribution of a molecule, and it has been calculated as the sum of spherical atom electron densities. 17 It was used to quantify the contribution of intermolecular interactions that stabilize the crystal packing and to understand the nature of intermolecular interactions. 18 The results show that, even with the same chemical structure, different polymorphs of donepezil have different spatial arrangements, interaction energies, and conformation.…”

Section: Introductionmentioning

confidence: 99%

Quantitative Analysis the Weak Non-Covalent Interactions of the Polymorphs of Donepezil

Xing

Zhang

et al. 2022

ACS Omega

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Donepezil has polymorphism. Different crystalline forms can exhibit different physicochemical properties and biological activities. Exploration of intermolecular interactions is essential to reveal the formation mechanism and differences in properties of polymorphs. This study explores the weak non-covalent intermolecular interactions of donepezil polymorphs through fully ab initio quantum mechanical methods, semi-empirical methods, and Hirshfeld surface analysis. The results show that the Hirshfeld surface analysis method can clearly and intuitively reveal the intermolecular interactions. Theoretical calculations using the atom–atom Coulomb–London–Pauli (AA-CLP) method were also performed to understand the interaction energies toward the total lattice energy. The value of the lattice energy was in accordance with the melting points of the donepezil polymorphs and brought to light the nature of thermal stability. In the specific energy distribution, the contribution of the dispersion force is the most prominent. Further interaction energy analysis found that within a distance of 3.8 Å from the center of the donepezil molecule, different crystalline forms of donepezil molecules have different interaction energies with surrounding molecules. The different interaction energies between polymorphs may lead to polymorphs with different physical–chemical properties.

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1-Hydroxynaphthalene-4-trifluoromethylphenyl chalcone and 3‑hydroxy-4-trifluoromethylphenyl flavone: A combined experimental, structural, in vitro AChE, BChE and in silico studies

Ghias

Ahmed

Sajjad

et al. 2022

Journal of Molecular Structure

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Exploring weak intermolecular interactions in two bis-1,3,4-oxadiazoles derivatives: A combined X-ray diffraction, Hirshfeld surface analysis and theoretical studies

Cited by 8 publications

References 54 publications

π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

π–π Noncovalent Interaction Involving 1,2,4- and 1,3,4-Oxadiazole Systems: The Combined Experimental, Theoretical, and Database Study

Quantitative Analysis the Weak Non-Covalent Interactions of the Polymorphs of Donepezil

1-Hydroxynaphthalene-4-trifluoromethylphenyl chalcone and 3‑hydroxy-4-trifluoromethylphenyl flavone: A combined experimental, structural, in vitro AChE, BChE and in silico studies

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