Single-Crystal Structure Analysis of Dicarboxamides: Impact of Heteroatoms on Hydrogen Bonding of Carboxamide Groups

Autor: Abdulrahman Mohabbat, Jasmin Salama, Philipp Seiffert, István Boldog, Christoph Janiak
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Crystals, Vol 14, Iss 9, p 811 (2024)
Druh dokumentu: article
ISSN: 2073-4352
DOI: 10.3390/cryst14090811
Popis: This research examines how heteroatoms in a six- or five-membered pyridine, thiophene or furan ring spacer between two carboxamide groups influence the hydrogen bonding for advancements in supramolecular chemistry and drug development. The solvent-free crystal structures of 3,5-pyridinedicarboxamide (PDC), 2,5-thiophenedicarboxamide (TDC) and 2,5-furandicarboxamide (FDC-subl, crystallized by sublimation), and the monohydrate structure of FDC-solv (crystallized from methanol) are described with the hydrogen-bonding analyzed by the Etter graph-set notation. The carbon atoms of the amide groups form an angle of 121° in PDC, 151° in TDC, 137° in FDC-solv and 135° in FDC-subl with the ring centroid. Only in the structure of PDC does the heteroatom act as an H-bond acceptor as part of a C11(6) chain. In TDC and FDC, the heteroatoms do not interact with the amide -NH2 groups.
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