Synthesis and Crystal Structure Analysis of Some Aromatic Imines of Syringaldehyde
A series of syringaldehyde imines with <i>para</i>-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 t...
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MDPI AG
2024-01-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/14/1/99 |
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| author | Christopher G. Hamaker Stephan M. Germann |
| author_facet | Christopher G. Hamaker Stephan M. Germann |
| author_sort | Christopher G. Hamaker |
| collection | DOAJ |
| description | A series of syringaldehyde imines with <i>para</i>-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<sup>…</sup>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 <i>cis</i> to the imine group give hydrogen-bonded zigzag chains in the monoclinic crystals, while the structure with a <i>trans</i> hydroxy group crystallize in a hexagonal space group (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>R</mi><mover accent="true"><mn>3</mn><mo>¯</mo></mover></mrow></semantics></math></inline-formula>) and form hydrogen-bonded hexamers. The hexagonal structure also displays Br<sup>…</sup>Br interactions, forming additional hexameric clusters. The analysis of published <i>p</i>-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. |
| first_indexed | 2024-03-08T09:55:02Z |
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| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-08T09:55:02Z |
| publishDate | 2024-01-01 |
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| series | Crystals |
| spelling | doaj.art-96024377d17f43e393d9c3c67e60f0522024-01-29T13:51:35ZengMDPI AGCrystals2073-43522024-01-011419910.3390/cryst14010099Synthesis and Crystal Structure Analysis of Some Aromatic Imines of SyringaldehydeChristopher G. Hamaker0Stephan M. Germann1Department of Chemistry, Illinois State University, Normal, IL 61790-4160, USADepartment of Chemistry, Illinois State University, Normal, IL 61790-4160, USAA series of syringaldehyde imines with <i>para</i>-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<sup>…</sup>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 <i>cis</i> to the imine group give hydrogen-bonded zigzag chains in the monoclinic crystals, while the structure with a <i>trans</i> hydroxy group crystallize in a hexagonal space group (<inline-formula><math xmlns="http://www.w3.org/1998/Math/MathML" display="inline"><semantics><mrow><mi>R</mi><mover accent="true"><mn>3</mn><mo>¯</mo></mover></mrow></semantics></math></inline-formula>) and form hydrogen-bonded hexamers. The hexagonal structure also displays Br<sup>…</sup>Br interactions, forming additional hexameric clusters. The analysis of published <i>p</i>-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.https://www.mdpi.com/2073-4352/14/1/99concomitant polymorphcrystal structureSchiff basehydrogen bonding |
| spellingShingle | Christopher G. Hamaker Stephan M. Germann Synthesis and Crystal Structure Analysis of Some Aromatic Imines of Syringaldehyde Crystals concomitant polymorph crystal structure Schiff base hydrogen bonding |
| title | Synthesis and Crystal Structure Analysis of Some Aromatic Imines of Syringaldehyde |
| title_full | Synthesis and Crystal Structure Analysis of Some Aromatic Imines of Syringaldehyde |
| title_fullStr | Synthesis and Crystal Structure Analysis of Some Aromatic Imines of Syringaldehyde |
| title_full_unstemmed | Synthesis and Crystal Structure Analysis of Some Aromatic Imines of Syringaldehyde |
| title_short | Synthesis and Crystal Structure Analysis of Some Aromatic Imines of Syringaldehyde |
| title_sort | synthesis and crystal structure analysis of some aromatic imines of syringaldehyde |
| topic | concomitant polymorph crystal structure Schiff base hydrogen bonding |
| url | https://www.mdpi.com/2073-4352/14/1/99 |
| work_keys_str_mv | AT christopherghamaker synthesisandcrystalstructureanalysisofsomearomaticiminesofsyringaldehyde AT stephanmgermann synthesisandcrystalstructureanalysisofsomearomaticiminesofsyringaldehyde |