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Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole
The title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C(1...
| Autores principales: | , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
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International Union of Crystallography
2023
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10242748/ https://www.ncbi.nlm.nih.gov/pubmed/37288462 http://dx.doi.org/10.1107/S2056989023004164 |
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| author | Okmanov, Rasul Ya. Ziyaev, Abdukhakim A. Abdukarimov, Azimboy Sh. Toshmurodov, Turdibek T. Kholikov, Tursunali S. |
| author_facet | Okmanov, Rasul Ya. Ziyaev, Abdukhakim A. Abdukarimov, Azimboy Sh. Toshmurodov, Turdibek T. Kholikov, Tursunali S. |
| author_sort | Okmanov, Rasul Ya. |
| collection | PubMed |
| description | The title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C(17)H(17)N(3)OS (I), and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C(17)H(15)ClFN(3)OS (II), were 96 and 92%, respectively. In the crystal structures of (I) and (II), C–H⋯π interactions are observed between neighboring molecules. Hirshfeld surface analysis indicates that H⋯H and H⋯C/C⋯H interactions make the most important contributions to the crystal packing. |
| format | Online Article Text |
| id | pubmed-10242748 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2023 |
| publisher | International Union of Crystallography |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-102427482023-06-07 Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole Okmanov, Rasul Ya. Ziyaev, Abdukhakim A. Abdukarimov, Azimboy Sh. Toshmurodov, Turdibek T. Kholikov, Tursunali S. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C(17)H(17)N(3)OS (I), and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C(17)H(15)ClFN(3)OS (II), were 96 and 92%, respectively. In the crystal structures of (I) and (II), C–H⋯π interactions are observed between neighboring molecules. Hirshfeld surface analysis indicates that H⋯H and H⋯C/C⋯H interactions make the most important contributions to the crystal packing. International Union of Crystallography 2023-05-19 /pmc/articles/PMC10242748/ /pubmed/37288462 http://dx.doi.org/10.1107/S2056989023004164 Text en © Okmanov et al. 2023 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
| spellingShingle | Research Communications Okmanov, Rasul Ya. Ziyaev, Abdukhakim A. Abdukarimov, Azimboy Sh. Toshmurodov, Turdibek T. Kholikov, Tursunali S. Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_full | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_fullStr | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_full_unstemmed | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_short | Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| title_sort | syntheses, crystal structures and hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole |
| topic | Research Communications |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10242748/ https://www.ncbi.nlm.nih.gov/pubmed/37288462 http://dx.doi.org/10.1107/S2056989023004164 |
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