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Anastasia V. Shishkina

Bio: Anastasia V. Shishkina is an academic researcher from D. Mendeleev University of Chemical Technology of Russia. The author has contributed to research in topics: Intermolecular force & Electron density. The author has an hindex of 7, co-authored 7 publications receiving 305 citations.

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TL;DR: In this article, a detailed description of noncovalent interactions of different types and strengths in the title crystal using a combined experimental and theoretical study of the charge density distribution is provided.
Abstract: This study provides a detailed description of noncovalent interactions of different types and strengths in the title crystal using a combined experimental and theoretical study of the charge density distribution. The nature of the noncovalent interactions is visualized using information theory and through the superposition of the gradient fields in the electron density and electrostatic potential. The energy of the intramolecular O–H···O bond, intermolecular C–H···O bonds, and π-stacking interactions, Eint, are evaluated from empirical correlations between Eint and geometrical and electron-density bond critical point parameters. The complete set of noncovalent interactions including the strong intramolecular O–H···O (Eint > 90 kJ/mol) and weak C–H···O (Eint < 10 kJ/mol) hydrogen bonds, and π-stacking interactions (Eint < 4 kJ/mol) is quantitatively described. The results from the experimental charge density analysis are compared with periodic quantum calculations using density functional theory with the G...

76 citations

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TL;DR: The structure, IR harmonic frequencies and intensities of normal vibrations of 20 molecular crystals with the X-Cl···Cl-X contacts of different types, and the obtained crystalline wave functions have been further used to define and describe quantitatively the Cl··· Cl interactions via the electron-density features at the Cl··Cl bond critical points.
Abstract: The structure, IR harmonic frequencies and intensities of normal vibrations of 20 molecular crystals with the X–Cl···Cl–X contacts of different types, where X = C, Cl, and F and the Cl···Cl distance varying from ∼3.0 to ∼4.0 A, are computed using the solid-state DFT method. The obtained crystalline wave functions have been further used to define and describe quantitatively the Cl···Cl interactions via the electron-density features at the Cl···Cl bond critical points. We found that the electron-density at the bond critical point is almost independent of the particular type of the contact or hybridization of the ipso carbon atom. The energy of Cl···Cl interactions, Eint, is evaluated from the linking Eint and local electronic kinetic energy density at the Cl···Cl bond critical points. Eint varies from 2 to 12 kJ/mol. The applicability of the geometrical criterion for the detection of the Cl···Cl interactions in crystals with two or more intermolecular Cl···Cl contacts for the unique chlorine atom is not str...

75 citations

Journal ArticleDOI
TL;DR: The classical method of substance transfer by inert gas-carrier was chosen to investigate sublimation processes experimentally and the lattice energy is found to be 143 ± 4 kJ/mol, lower than the sum of the corresponding values of the cocrystal pure components.
Abstract: A new cocrystal of 2-hydroxybenzamide (A) with 4-acetamidobenzoic acid (B) has been obtained by the DSC screening method. Thermophysical analysis of the aggregate [A:B] has been conducted and a fusion diagram has been plotted. Cocrystal formation from melts was studied by using thermomicroscopy. A cocrystal single-crystal was grown and its crystal structure was determined. The pattern of noncovalent interactions has been quantified using the solid-state DFT computations coupled with the Bader analysis of the periodic electron density. The sublimation processes of A-B cocrystal have been studied and its thermodynamic functions have been calculated. The classical method of substance transfer by inert gas-carrier was chosen to investigate sublimation processes experimentally. The lattice energy is found to be 143 ± 4 kJ/mol. It is lower than the sum of the corresponding values of the cocrystal pure components. The theoretical value of the lattice energy, 156 kJ/mol, is in reasonable agreement with the experi...

58 citations

Journal ArticleDOI
TL;DR: A detailed description of the ability of halogen bonding to control recognition, self-organization, and self-assembly in I2 crystal, combining low-temperature X-ray diffraction experiments and theoretical DFT-D and MP2 studies of charge density, is reported in this article.
Abstract: A detailed description of the ability of halogen bonding to control recognition, self-organization, and self-assembly in I2 crystal, combining low-temperature X-ray diffraction experiments and theoretical DFT-D and MP2 studies of charge density, is reported. The bond critical point features were analyzed using the bonding ellipsoids, in order to make them more evident and easier to compare. We showed that one-electron potential, in contrast to Laplacian of electron density, allows the electron concentration and depletion regions in the valence shell of the iodine atoms to be revealed. Thus, it was demonstrated as an effective tool for understanding the molecular recognition processes in iodine crystal, describing the mutually complementary areas of concentration and depletion of electron density in adjacent molecules. This finding was also confirmed in terms of electrostatic potential, especially using the concept of σ-hole. The tiny features of the electrostatic component of halogen–halogen interactions ...

52 citations

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TL;DR: It was proved that PASA cocrystallization with 4-OHBZA makes the drug more stable and prevents the irreversible process of decarboxylation of PAS a resulting in formation of toxic 3-aminophenol.
Abstract: Cocrystal screening of 4-hydroxybenzamide with a number of salicylates (salicylic acid, SA; 4-aminosalicylic acid, PASA; acetylsalicylic acid, ASA; and salicylsalicylic acid, SSA) was conducted to confirm the formation of two cocrystals, [SA+4-OHBZA] (1:1) and [PASA+4-OHBZA] (1:1). Their structures were determined using single-crystal X-ray diffraction, and the hydrogen-bond network topology was studied. Thermodynamic characteristics of salicylic acid cocrystal sublimation were obtained experimentally. It was proved that PASA cocrystallization with 4-OHBZA makes the drug more stable and prevents the irreversible process of decarboxylation of PASA resulting in formation of toxic 3-aminophenol. The pattern of non-covalent interactions in the cocrystals is described quantitatively using solid-state density functional theory followed by Bader analysis of the periodic electron density. It has been found that the total energy of secondary interactions between synthon atoms and the side hydroxyl group of the aci...

37 citations


Cited by
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TL;DR: The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.
Abstract: The halogen bond occurs when there is evidence of a net attractive interaction between an electrophilic region associated with a halogen atom in a molecular entity and a nucleophilic region in another, or the same, molecular entity. In this fairly extensive review, after a brief history of the interaction, we will provide the reader with a snapshot of where the research on the halogen bond is now, and, perhaps, where it is going. The specific advantages brought up by a design based on the use of the halogen bond will be demonstrated in quite different fields spanning from material sciences to biomolecular recognition and drug design.

2,582 citations

Journal ArticleDOI
TL;DR: This overview shows how the overlap of previously unrelated areas of mechanochemical screening for API solid forms, organic synthesis by milling, and mechanochemical screenings for molecular recognition enables the emergence of a new research discipline in which different aspects of pharmaceutical and medicinal chemistry are addressed through mechanochemistry rather than through conventional solution-based routes.

266 citations

Journal ArticleDOI
TL;DR: A tutorial review aimed at both the novice and the seasoned solid-state chemist provides a succinct overview of key findings that have, over the last half century, advanced our ability to make molecular crystals with targeted structures and desired properties.
Abstract: This Tutorial Review, aimed at both the novice and the seasoned solid-state chemist, provides a succinct overview of key findings that have, over the last half century, advanced our ability to make molecular crystals with targeted structures and desired properties. The article critically evaluates the efficiency and reliability of the well-established guidelines used by experimentalists in crystal engineering and highlights statistical and computational tools that are both advantageous to crystal design and accessible to experimental solid-state chemists.

193 citations

Journal ArticleDOI
TL;DR: A compendium of phase change enthalpies including fusion, vaporization, and sublimation was published in 2010 as mentioned in this paper, which included organic, organometallic, and a few inorganic compounds.
Abstract: A compendium of phase change enthalpies published in 2010 is updated to include the period 1880–2015. Phase change enthalpies including fusion, vaporization, and sublimation enthalpies are included for organic, organometallic, and a few inorganic compounds. Part 1 of this compendium includes organic compounds from C1 to C10. Part 2 of this compendium, to be published separately, will include organic and organometallic compounds from C11 to C192. Sufficient data are presently available to permit thermodynamic cycles to be constructed as an independent means of evaluating the reliability of the data. Temperature adjustments of phase change enthalpies from the temperature of measurement to the standard reference temperature, T = 298.15 K, and a protocol for doing so are briefly discussed.

191 citations

Journal ArticleDOI
01 Sep 2015-IUCrJ
TL;DR: A combination of single-crystal X-ray and neutron diffraction experiments are used to determine the electron density distribution in orthorhombic rubrene and clearly demonstrate the presence of π⋯π stacking interactions in the crystalline state.

176 citations