2021
DOI: 10.1021/acs.cgd.1c00758
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Abstract: New racemic and enantiopure N-phosphorylated thioureas bearing 1phenylethyl or tetrahydronaphthalenyl fragments were synthesized. According to NMR data assisted by DFT calculations, the preferred conformation is stabilized by an intramolecular hydrogen bond. This form in solution is in equilibrium with dimeric N− H•••S hydrogen-bonded associates, the population depending on the concentration. In the crystalline phase the low-energy conformation with an intramolecular H-bond is realized only in the racemic tetr… Show more

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Cited by 3 publications
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“…Polymorphic phase transition, defined as a transition of a crystalline phase at a certain temperature and pressure to another crystalline phase of the same composition with different crystal structures, is a critical phenomenon in the field of pharmaceutical chemistry because the different physical properties of polymorphs such as bioavailability and solubility also have intellectual property rights. , Crystal structures with a large number of molecules in the asymmetric unit ( Z ′), i.e., high- Z ′, are not only a scientific curiosity but also attract many scientists as an informative subset of crystal structures to understand crystallization and polymorphism. Indeed, the new crystal structure of a simple compound, the hydrochloride salt of fampridine, where Z ′ = 30, was recently reported as a Frank–Kasper (FK) phase, and this class of materials is expected to open new perspectives in the field of supramolecular chemistry and material science . Peptide compounds, which have recently attracted attention as building blocks of porous materials , and are being developed for use as a promising class of molecular pharmaceutics, have been reported to exhibit many polymorphs due to the conformational flexibility derived from the side chain structure of amino acids.…”
Section: Introductionmentioning
confidence: 99%
“…Polymorphic phase transition, defined as a transition of a crystalline phase at a certain temperature and pressure to another crystalline phase of the same composition with different crystal structures, is a critical phenomenon in the field of pharmaceutical chemistry because the different physical properties of polymorphs such as bioavailability and solubility also have intellectual property rights. , Crystal structures with a large number of molecules in the asymmetric unit ( Z ′), i.e., high- Z ′, are not only a scientific curiosity but also attract many scientists as an informative subset of crystal structures to understand crystallization and polymorphism. Indeed, the new crystal structure of a simple compound, the hydrochloride salt of fampridine, where Z ′ = 30, was recently reported as a Frank–Kasper (FK) phase, and this class of materials is expected to open new perspectives in the field of supramolecular chemistry and material science . Peptide compounds, which have recently attracted attention as building blocks of porous materials , and are being developed for use as a promising class of molecular pharmaceutics, have been reported to exhibit many polymorphs due to the conformational flexibility derived from the side chain structure of amino acids.…”
Section: Introductionmentioning
confidence: 99%