N,N′-Di(pyridine-4-yl)-pyridine-3,5-dicarboxamide, a Pincer-Type Tricationic Compound; Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and Computational Chemistry Studies

Ayiya, Bitrus Bikimi; Okpareke, Obinna C.

doi:10.1007/s10870-021-00902-4

Cited by 3 publications

(3 citation statements)

References 21 publications

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“…Although the values of the decomposed molecular fingerprint components give a pseudoquantitative weight of the various types of contacts, the calculation of the interaction energy profile of the two structures could help to get better understand about the stabilization features [40][41][42]. Therefore, the intermolecular interaction energies for Aux-A and Aux-B are calculated using HF/3-21G level of theory energy model available in Crystal-Explorer (CE) functionality [23].…”

Section: The Increasing Of the Percentage Of H•••h And H•••o Contacts Inmentioning

confidence: 99%

Describing auxin solid state intermolecular interactions using contact descriptors, shape property and molecular fingerprint: comparison of pure auxin crystal and auxin-TIR1 co-crystal

Etsè

Quashie

2022

Eur J Chem

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This work reports for the first time, the analysis of intermolecular interactions in crystal structures of auxin (Indole-3-acetic acid) crystallized as pure sample (Aux-A) or co-crystallized with transport inhibitor response 1 (Aux-B). Using crystal packing of pure auxin and a cluster of residues in a radius of 6 Å around this ligand in the transport inhibitor response 1 binding domain, various properties were calculated and mapped on the Hirshfeld surface (HS). The HSs of the two molecules are characterized by close parameters of volume, area, globularity, and asphericity revealing the efficiency of the considered cluster. The HS mapped over descriptors like de, di and dnorm showed red spots corresponding to hydrogen bonds contacts. In addition to the shape index and curvedness descriptors, the results highlight weak interactions stabilizing the auxin structures. The analyses of electrostatic potential, electron density, and deformation density maps confirm the slightly change in the electron donor and acceptor groups localization. Furthermore, the molecular fingerprint analyses revealed a notable discrepancy in the shape and percentage value of the various contacts. Decomposition of the fingerprint shows that the contributions of important contacts (H···H, H···O, and O···O) are higher in Aux-B than in Aux-A. Finally, the quantitative approach by the determination of the molecular interaction energies of the two structures in their respective crystallographic environment revealed that Aux-A is slightly more stabilized than Aux-B.

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Section: The Increasing Of the Percentage Of H•••h And H•••o Contacts Inmentioning

confidence: 99%

Describing auxin solid state intermolecular interactions using contact descriptors, shape property and molecular fingerprint: comparison of pure auxin crystal and auxin-TIR1 co-crystal

Etsè

Quashie

2022

Eur J Chem

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confidence: 99%

“…electrostatic (E ele ), polarization (E pol ), dispersion (E dis ), and exchange repulsion (E rep )(Tan et al, 2019;Ayiya & Okpareke, 2021). The energies were obtained by calculating the wave function of each pair of molecules or atoms at the B3LYP/6-31G(d,p) level of theory(Ayiya & Okpareke, 2021;Izuogu et al, 2020). Quantitative estimations of the strength and nature of the intermolecular interactions in title compound crystal with individual energy components (E ele , E pol , E dis , and E rep ) as well as the sum of the energy components E tot are presented in Table…”

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confidence: 99%

Crystal structure, Hirshfeld surface and computational study of 1-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-propanoylthiourea

Ifeanyieze¹,

Ayiya²,

Okpareke³

et al. 2022

Acta Cryst E

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The title compound, C18H14N2O3S, crystallizes in the orthorhombic crystal system and Pbca space group. The thiourea chromophore is planar to an r.m.s deviation of 0.032 Å with the thiolate sulfur atom being the most deviated. Bifurcated N—H...O intramolecular hydrogen bonds result in an S(6) supramolecular synthon. In the crystal, molecules are linked by N—H...O intermolecular hydrogen-bonding interactions and stabilized by C—H...π and π–π interactions. Hirshfeld surface analysis and fingerprint plot indicate the H...H intermolecular contacts as the highest contributor to the overall surface contacts (38%) and this is supported by the high dispersive and electrostatic interaction energies.

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Synthesis, structure, hirshfeld surface analysis, non-covalent interaction, and in silico studies of 4-hydroxy-1-[(4-nitrophenyl)sulphonyl]pyrrolidine-2-carboxyllic acid

Ugwu

Eze

Ezeorah

et al. 2022

Preprint

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The new compound 4-hydroxy-1-[(4-nitrophenyl)sulphonyl]pyrrolidine-2-carboxyllic acid was obtained by the reaction of 4-hydroxyproline with 4-nitrobenzenesulphonyl chloride. The compound was characterized using X-ray diffraction studies. Spectroscopic methods including NMR, FTIR, ES-MS, and UV were employed for further structural analysis of the synthesized compound. The title compound was found to have crystallized in an orthorhombic crystal system with space group P212121. The S1-N1 bond length of 1.628 (2) Å was a strong indication of the formation of the title compound. The absence of characteristic downfield 1H NMR peak of pyrrolidine ring and the presence of S-N stretching vibration at 857.82 cm− 1 on the FTIR are strong indications for the formation of the sulfonamide. The experimental study was complemented with computations at the B3LYP/6-311G++(d,p) level of theory to gain more understanding of interactions in the compound at the molecular level. Noncovalent interaction, Hirsfeld surface analysis and interaction energy calculations were employed in the analysis of the supramolecular architecture of the compound. Predicted ADMET parameters, awarded suitable bioavailability credentials, while the molecular docking study indicated that the compound enchants promising inhibition prospects against dihydropteroate synthase, DNA topoisomerase, and SARS-CoV-2 spike.

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N,N′-Di(pyridine-4-yl)-pyridine-3,5-dicarboxamide, a Pincer-Type Tricationic Compound; Synthesis, Crystal Structure, Hirshfeld Surface Analysis, and Computational Chemistry Studies

Cited by 3 publications

References 21 publications

Describing auxin solid state intermolecular interactions using contact descriptors, shape property and molecular fingerprint: comparison of pure auxin crystal and auxin-TIR1 co-crystal

Describing auxin solid state intermolecular interactions using contact descriptors, shape property and molecular fingerprint: comparison of pure auxin crystal and auxin-TIR1 co-crystal

Crystal structure, Hirshfeld surface and computational study of 1-(9,10-dioxo-9,10-dihydroanthracen-1-yl)-3-propanoylthiourea

Synthesis, structure, hirshfeld surface analysis, non-covalent interaction, and in silico studies of 4-hydroxy-1-[(4-nitrophenyl)sulphonyl]pyrrolidine-2-carboxyllic acid

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