Solid-State Photoinitiated Cycloaddition Reaction of 4,4′-(Ethene-1,2-diyl)bis(pyridinium) Dinitrate: Charge-Density Perspective on Initial Stage of the Reaction

Вологжанина, Анна В.; Aleshin, Dmitry Yu.; Volodin, Alexander D.; Savchenkov, Anton V.; Ushakov, Ivan E.; Korlyukov, Alexander A.

doi:10.3390/cryst9120613

Cited by 3 publications

(1 citation statement)

References 53 publications

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“…The [2 + 2] photodimerization of 1,2-di(4-pyridyl)ethylene, bpe (Figure a), in photostable matrices has been vastly studied, − starting from bpe and resorcinol cocrystals, , which are the flagship example showing how crystal structures can be modified in order to obtain materials of desired properties. The [2 + 2] photodimerization of bpe can lead to different isomers (Figure b), which is a consequence of crystal packing …”

Section: Introductionmentioning

confidence: 99%

Influence of High Pressure on the Pedal-like Motion and Photoreactivity in the Cocrystals of 1,2-Di(4-pyridyl)ethylene with trans-2-(4-Fluorophenyl)vinylboronic Acid

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Dračínský

Szyja

et al. 2022

Crystal Growth & Design

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The photochemical properties of 1,2-di(4-pyridyl)ethylene (bpe) and trans-2-(4-fluorophenyl)vinylboronic acid (fpvb) cocrystals have been investigated using complementary techniques: single-crystal X-ray diffraction, including high-pressure experiments, solid-state and solution nuclear magnetic resonance, and density functional theory calculations. The photochemistry of bpe and fpvb cocrystals strongly depends on the arrangement of bpe molecules. The [2 + 2] photodimerization of bpe occurs in the case of the bpe/fpvb ratio of 1:1, while a ratio of 1:2 is observed in photoinert objects. In the photoreactive cocrystals, a pedal-like motion occurs in bpe molecules. This phenomenon strongly affects photoreactivity because it changes the mutual geometry of two reactant molecules. The intermolecular geometry and the kinetics of the pedal-like motion, and thereby, the kinetics of the [2 + 2] photodimerization of bpe, have been modified by means of high pressure.

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Section: Introductionmentioning

confidence: 99%

Influence of High Pressure on the Pedal-like Motion and Photoreactivity in the Cocrystals of 1,2-Di(4-pyridyl)ethylene with trans-2-(4-Fluorophenyl)vinylboronic Acid

Konieczny

Dračínský

Szyja

et al. 2022

Crystal Growth & Design

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Charge density analysis of abiraterone acetate

Korlyukov

Вологжанина

Trzybiński

et al. 2020

Acta Crystallogr Sect B

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A high-resolution single-crystal X-ray diffraction study of abiraterone acetate (1) has been carried out. The charge density distribution in the crystal of this anticancer drug is reconstructed from experimental data. The nature and the contributions of various intermolecular interactions to the total crystal energy are studied by means of the quantum theory `Atoms-in-Molecules', a non-covalent interactions method and energy framework plots. In general, dispersion C—H...H—C and C—H...π interactions play the main role in crystal packing of 1. The Voronoi tessellation analysis of 1 confirmed that contribution of hydrophobic and hydrophilic interactions to the molecular surface is close to their contribution to the total crystal energy. Similar analysis of abiraterone complexes with the cytochrome P450 family demonstrated that contribution of the C—H...H—C and C—H...π interactions to the molecular surface of the drug remains unchanged to fit the binding pocket, despite the presence of water and heme molecules, and hydrophilic groups within the pocket.

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Intermolecular Interactions in Crystal Structures of Imatinib-Containing Compounds

Вологжанина

Ushakov

Korlyukov

2020

IJMS

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Imatinib, one of the most used therapeutic agents to treat leukemia, is an inhibitor that specifically blocks the activity of tyrosine kinases. The molecule of imatinib is flexible and contains several functional groups able to take part in H-bonding and hydrophobic interactions. Analysis of molecular conformations for this drug was carried out using density functional theory calculations of rotation potentials along single bonds and by analyzing crystal structures of imatinib-containing compounds taken from the Cambridge Structural Database and the Protein Data Bank. Rotation along the N-C bond in the region of the amide group was found to be the reason for two relatively stable molecular conformations, an extended and a folded one. The role of various types of intermolecular interactions in stabilization of the particular molecular conformation was studied in terms of (i) the likelihood of H-bond formation, and (ii) their contribution to the Voronoi molecular surface. It is shown that experimentally observed hydrogen bonds are in accord with the likelihood of their formation. The number of H-bonds in ligand-receptor complexes surpasses that in imatinib salts due to the large number of donors and acceptors of H-bonding within the binding pocket of tyrosine kinases. Contribution of hydrophilic intermolecular interactions to the Voronoi molecular surface is similar for both conformations, while π...π stacking is more typical for the folded conformation of imatinib.

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Solid-State Photoinitiated Cycloaddition Reaction of 4,4′-(Ethene-1,2-diyl)bis(pyridinium) Dinitrate: Charge-Density Perspective on Initial Stage of the Reaction

Cited by 3 publications

References 53 publications

Influence of High Pressure on the Pedal-like Motion and Photoreactivity in the Cocrystals of 1,2-Di(4-pyridyl)ethylene with trans-2-(4-Fluorophenyl)vinylboronic Acid

Influence of High Pressure on the Pedal-like Motion and Photoreactivity in the Cocrystals of 1,2-Di(4-pyridyl)ethylene with trans-2-(4-Fluorophenyl)vinylboronic Acid

Charge density analysis of abiraterone acetate

Intermolecular Interactions in Crystal Structures of Imatinib-Containing Compounds

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