Synthesis and Crystal Structure Analysis of Some Aromatic Imines of Syringaldehyde

Autor: Christopher G. Hamaker, Stephan M. Germann
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Crystals, Vol 14, Iss 1, p 99 (2024)
Druh dokumentu: article
ISSN: 2073-4352
DOI: 10.3390/cryst14010099
Popis: A series of syringaldehyde imines with para-substituted anilines have been synthesized in a good yield, and their crystal structures have been analyzed. The orientation of the syringaldehyde hydroxyl group plays in important role in the intermolecular hydrogen-bonding pattern of the molecules. The O–H…N hydrogen bonding interactions primarily determine the three-dimensional packing of the molecules, even though they make up a relatively small percentage of intermolecular interactions in the molecules. The three structures with the p-hydroxy group cis to the imine group give hydrogen-bonded zigzag chains in the monoclinic crystals, while the structure with a trans hydroxy group crystallize in a hexagonal space group (R3¯) and form hydrogen-bonded hexamers. The hexagonal structure also displays Br…Br interactions, forming additional hexameric clusters. The analysis of published p-hydroxyphenyl imine crystal structures from the Cambridge Crystallographic Database revealed patterns in the length of the hydrogen bonding interactions based on steric congestion around the hydroxyl group.
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