Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds
Synthetic supramolecular structures constructed through the cooperative action of numerous non-covalent forces are highly desirable as models to unravel and understand the complexity of systems created in nature via self-assembly. Taking advantage of the low cost of 2,4,6-trichloro-1,3,5-triazine (c...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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The Royal Society
2022-11-01
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| Series: | Royal Society Open Science |
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| Online Access: | https://royalsocietypublishing.org/doi/10.1098/rsos.220603 |
| _version_ | 1797845366376235008 |
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| author | Shazia Asghar Shahid Hameed Muhammad Nawaz Tahir Muhammad Moazzam Naseer |
| author_facet | Shazia Asghar Shahid Hameed Muhammad Nawaz Tahir Muhammad Moazzam Naseer |
| author_sort | Shazia Asghar |
| collection | DOAJ |
| description | Synthetic supramolecular structures constructed through the cooperative action of numerous non-covalent forces are highly desirable as models to unravel and understand the complexity of systems created in nature via self-assembly. Taking advantage of the low cost of 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) and the sequential nucleophilic substitution reactions with almost all types of nucleophiles, a series of six structurally related novel s-triazine derivatives 1–6 were synthesized and structurally characterized based on their physical, spectral and crystallographic data. The solid-state structures of all the six compounds showed intriguing and unique molecular duplexes featuring NH···N, CH···O and CH···π interactions. Careful analysis of different geometric parameters of the involved H-bonds indicates that they are linear, significant and are therefore responsible for guiding the three-dimensional structure of these compounds in the solid state. The prevalence of sextuple hydrogen bond array-driven molecular duplexes and the possibility of structural modifications on the s-triazine ring render these novel triazine derivatives 1–6 attractive as a platform to create heteroduplex constructs and their subsequent utility in the field of supramolecular chemistry and crystal engineering. |
| first_indexed | 2024-04-09T17:37:54Z |
| format | Article |
| id | doaj.art-e2239164283144db80c7ac88869aadc4 |
| institution | Directory Open Access Journal |
| issn | 2054-5703 |
| language | English |
| last_indexed | 2024-04-09T17:37:54Z |
| publishDate | 2022-11-01 |
| publisher | The Royal Society |
| record_format | Article |
| series | Royal Society Open Science |
| spelling | doaj.art-e2239164283144db80c7ac88869aadc42023-04-17T10:54:42ZengThe Royal SocietyRoyal Society Open Science2054-57032022-11-0191110.1098/rsos.220603Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compoundsShazia Asghar0Shahid Hameed1Muhammad Nawaz Tahir2Muhammad Moazzam Naseer3Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Physics, University of Sargodha, Sargodha 40100, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanSynthetic supramolecular structures constructed through the cooperative action of numerous non-covalent forces are highly desirable as models to unravel and understand the complexity of systems created in nature via self-assembly. Taking advantage of the low cost of 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) and the sequential nucleophilic substitution reactions with almost all types of nucleophiles, a series of six structurally related novel s-triazine derivatives 1–6 were synthesized and structurally characterized based on their physical, spectral and crystallographic data. The solid-state structures of all the six compounds showed intriguing and unique molecular duplexes featuring NH···N, CH···O and CH···π interactions. Careful analysis of different geometric parameters of the involved H-bonds indicates that they are linear, significant and are therefore responsible for guiding the three-dimensional structure of these compounds in the solid state. The prevalence of sextuple hydrogen bond array-driven molecular duplexes and the possibility of structural modifications on the s-triazine ring render these novel triazine derivatives 1–6 attractive as a platform to create heteroduplex constructs and their subsequent utility in the field of supramolecular chemistry and crystal engineering.https://royalsocietypublishing.org/doi/10.1098/rsos.220603triazine derivativesself-assemblymolecular duplexesCH···O interactionsCH···π interactionssupramolecular synthons |
| spellingShingle | Shazia Asghar Shahid Hameed Muhammad Nawaz Tahir Muhammad Moazzam Naseer Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds Royal Society Open Science triazine derivatives self-assembly molecular duplexes CH···O interactions CH···π interactions supramolecular synthons |
| title | Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds |
| title_full | Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds |
| title_fullStr | Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds |
| title_full_unstemmed | Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds |
| title_short | Molecular duplexes featuring NH···N, CH···O and CH···π interactions in solid-state self-assembly of triazine-based compounds |
| title_sort | molecular duplexes featuring nh···n ch···o and ch···π interactions in solid state self assembly of triazine based compounds |
| topic | triazine derivatives self-assembly molecular duplexes CH···O interactions CH···π interactions supramolecular synthons |
| url | https://royalsocietypublishing.org/doi/10.1098/rsos.220603 |
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