The formation of two thiotriazoline polymorphs: study from the energetic viewpoint

Shishkina, Svitlana V.; Baumer, V. N.; Khromileva, Olga V.; Kucherenko, L. I.; Mazur, I. A.

doi:10.1039/c7ce00117g

Cited by 8 publications

(13 citation statements)

References 32 publications

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“…The polymorphic forms I and II have the same packing type (columnar-layered), and the packing of DBUs is more anisotropic in the most stable polymorph I . The obtained regularities between crystal structure stability and the degree of its packing anisotropy correlate with previously published data. , …”

Section: Resultssupporting

confidence: 89%

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Quantum Chemical Study on Mefenamic Acid Polymorphic Forms

et al. 2022

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Three polymorphic structures of mefenamic acid, which is a very popular drug, have been studied using quantum chemical methods. It has been shown that the centrosymmetric dimer formed due to two O–H···O hydrogen bonds is a complex building unit in all of the polymorphic structures under study. On the basis of an analysis of the pairwise interaction energies between molecules, the polymorphic forms I and II are classified as columnar-layered while the polymorphic form III has a columnar structure. The stabilities of the three polymorphic forms of mefenamic acid under ambient conditions ( I > II > III ) correlate with the degree of anisotropy of the interaction energies between columns (primary basic structural motifs) formed due to stacking interactions. The shear deformation modeling of strongly bound layers in all of the polymorphic structures has not revealed any possibility for deformation of the crystal structure. The construction of the shift energy profiles and calculation of the energy barriers for the displacement along the (100) crystallographic plane in the [100], [010], and [011] crystallographic directions make it possible to explain the experimental data obtained for commercially available polymorphic structure I in a diamond anvil cell. The absence of any local minimum near the starting point on the shift energy profile and the extremely high energy barrier can be considered as criteria for the impossibility of a crystal structure deformation under pressure.

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Section: Resultssupporting

confidence: 89%

“…The obtained regularities between crystal structure stability and the degree of its packing anisotropy correlate with previously published data. 35 , 36 …”

Section: Resultsmentioning

confidence: 99%

Quantum Chemical Study on Mefenamic Acid Polymorphic Forms

et al. 2022

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“…Thermodynamical control is associated with slow evaporation, slow crystallization from the melt, or slow sublimation. Our recent study has shown that crystallization processes of different types may result in different arrangements of the molecules within the crystal phase …”

Section: Introductionmentioning

confidence: 99%

“…Our recent study has shown that crystallization processes of different types may result in different arrangements of the molecules within the crystal phase. 23 Molecular crystal formation principles have been studied for a long time. The first approach has been suggested by Kitaigorodsky who concluded that organic molecules crystallize according to close packing principle: "... the mutual arrangement of the molecules in a crystal is always such that the "projections" of one molecule fit into the "hollows" of adjacent molecules".…”

Section: ■ Introductionmentioning

confidence: 99%

Usage of Quantum Chemical Methods to Understand the Formation of Concomitant Polymorphs of Acetyl 2-(N-(2-Fluorophenyl)imino)coumarin-3-carboxamide

et al. 2021

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Crystallization of concomitant polymorphs is a very intriguing process that is difficult to be studied experimentally. A comprehensive study of two polymorphic modifications of acetyl 2-(N-(2-fluorophenyl)imino)coumarin-3-carboxamide using quantum chemical methods has revealed molecular and crystal structure dependence on crystallization conditions. Fast crystallization associated with a kinetically controlled process results in the formation of a columnar structure with a nonequilibrium molecular conformation and more isotropic topology of interaction energies between molecules. Slow crystallization may be considered as a thermodynamically controlled process and leads to the formation of a layered crystal structure with the conformation of the molecule corresponding to local minima and anisotropic topology of interaction energies. Fast crystallization results in the formation of a lot of weak intermolecular interactions, while slow crystallization leads to the formation of small amounts of stronger interactions.

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“…The gained knowledge may find a use in designing of materials having layered and corrugated arrangement of molecules. The modeling and synthesis of such materials are difficult but these processes without a doubt are much interest to crystal engineers . For chemists working at the molecular level, an appropriate arrangements of molecules in a crystal is achieved by modulating the noncovalent interactions through rational molecular design .…”

Section: Introductionmentioning

confidence: 99%

Quantitative Analysis of Intermolecular Interactions in 3‐Cyano‐2‐Pyridones: Evaluation through Single Crystal X‐ray Diffraction and Density Functional Theory

et al. 2018

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A series of 2-pyridones and their methyl derivatives has been studied in term of noncovalent interactions and molecular packing properties. These structural characteristics were then correlated with the quantitative analysis of the intermolecular interactions governing those compounds in three dimensional net. The electronic effect over the 2-pyridone ring on the packing property was analysed by locking the tautomers. The SC-XRD revealed that 4,6-dimethyl-3-cyano-2-pyridone and its O-methyl derivative owned the layered arrangement, while Nmethyl derivative possessed the corrugated arrangement with persistent of stacking between two pyridone rings. However, 4phenyl-6-methyl-3-cyano-2-pyridone and its N-methyl derivative showed the reverse face-to-face stacking due to modest torsion of bi-aryl rings. Similarly, 6-phenyl-4-methyl-3-cyano-2pyridone has also shown reverse face-to-face stacking while its N-methyl derivative stacking between pyridone ring and nitrile group was observed. Further, quantitative analysis of intermolecular interactions was done through Hirshfeld surface analysis and density functional theory.[a] Dr.

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The formation of two thiotriazoline polymorphs: study from the energetic viewpoint

Cited by 8 publications

References 32 publications

Quantum Chemical Study on Mefenamic Acid Polymorphic Forms

Quantum Chemical Study on Mefenamic Acid Polymorphic Forms

Usage of Quantum Chemical Methods to Understand the Formation of Concomitant Polymorphs of Acetyl 2-(N-(2-Fluorophenyl)imino)coumarin-3-carboxamide

Quantitative Analysis of Intermolecular Interactions in 3‐Cyano‐2‐Pyridones: Evaluation through Single Crystal X‐ray Diffraction and Density Functional Theory

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