Quantitative insights into energy contributions of intermolecular interactions in fluorine and trifluoromethyl substituted isomeric N-phenylacetamides and N-methylbenzamides

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Experimental and computational insights into the nature of weak intermolecular interactions in trifluoromethyl-substituted isomeric crystalline N-methyl-N-phenylbenzamides

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Role of intermolecular interactions involving organic fluorine in trifluoromethylated benzanilides

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Novel Azepino-perylenebisimides: Synthesis, Structure, and Properties

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Quantitative Investigation of Polymorphism in 3-(Trifluoromethyl)-N-[2-(trifluoromethyl) phenyl] benzamide

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Experimental and Theoretical Characterization of Short H‑Bonds with Organic Fluorine in Molecular Crystals

The existence of short H-bonds with organic fluorine is still under debate. We report herein the occurrence and nature of such short contacts to fluorine connected to an aromatic ring in the block form of <i>N</i>-(4-fluorophenyl)-3-(trifluoromethyl) benzamide and 4-fluoro-<i>N</i>-[3-(trifluoromethyl)­phenyl]­benzamide. The magnitude of the stabilizing interaction energy is −2.15 and −2.89 kcal/mol, respectively. It is important to note that such contacts have been observed in the presence of strong NH···OC H-bonds whose energies are in the range of 6.0–8.0 kcal/mol. Thus, the observed strength of an H-bond with fluorine is ∼30–40% of the strength of a strong traditional H-bond in amides. The acidic hydrogens were observed to be involved in the formation of a short CH···F contact, the interaction energy having a substantial Coulombic contribution in comparison to the other weak interactions which are primarily of a dispersive character as obtained by PIXEL method. A full topological analysis does establish the fact that CH···F interactions at short distances are indeed a “true H-bond”. These are not a consequence of crystal packing and have implications in the generation of polymorphs in the solid state. This is expected to have implications in the binding of a ligand (organic molecule containing fluorine) with the protein active site

Experimental and computational analysis of supramolecular motifs involving C sp2 (aromatic)--F and CF 3 groups in organic solids

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Quantitative analysis of intermolecular interactions in 7-hydroxy-4-methyl-2H-chromen-2-one and its hydrate

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Development of a Surface Coating Technique with Predictive Value for Bead Coating in the Manufacturing of Amorphous Solid Dispersions

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Similarities and differences in the crystal packing of halogen-substituted indole derivatives

The role of different intermolecular interactions in the crystal structures of halogen-substituted indoles which are fused with six-membered or seven-membered cyclic rings is investigated here. Several crystal structures show isostructural characteristics due to the presence of similar supramolecular motifs. In the absence of any strong hydrogen bonds, the molecular packing of reported structures is primarily stabilized by the presence of non-classical N—H…π and C—H…π interactions in addition to C—H…X (X = F/Cl/Br) interactions. The nature and energetics of primary and secondary dimeric motifs are partitioned into the electrostatics, polarization, dispersion and exchange–repulsion components using the PIXEL method. Short and directional N—H…π interactions are further explored by a topological analysis of the electron density based on quantum theory of atoms in molecules.SCOPUS: ar.jinfo:eu-repo/semantics/publishe