Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrroles
The crystal structures of three S-(pyridin-2-yl) benzothioesters with varying para-phenyl substituents are presented, namely, S-(pyridin-2-yl) 4-nitrobenzothioate (1, C12H8N2O3S), S-(pyridin-2-yl) 4-methylbenzothioate (2, C13H11NO2S) and S-(pyridin-2-yl) 4-methoxybenzothioate (3, C13H11NO2S). This c...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2023-03-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989023001056 |
| _version_ | 1811158127693791232 |
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| author | Harry C. Sample Brendan Twamley Mathias O. Senge |
| author_facet | Harry C. Sample Brendan Twamley Mathias O. Senge |
| author_sort | Harry C. Sample |
| collection | DOAJ |
| description | The crystal structures of three S-(pyridin-2-yl) benzothioesters with varying para-phenyl substituents are presented, namely, S-(pyridin-2-yl) 4-nitrobenzothioate (1, C12H8N2O3S), S-(pyridin-2-yl) 4-methylbenzothioate (2, C13H11NO2S) and S-(pyridin-2-yl) 4-methoxybenzothioate (3, C13H11NO2S). This class of compounds are used in the mono-acylation of pyrrolic species to yield multifunctional tetrapyrroles. The structures presented herein are the first of their compound class. The dominant interactions present in this series are π–π stacking and C—H...O interactions, and as the para-phenyl motif changes from electron withdrawing (NO2, 1) to electron donating (OCH3, 3), changes are observed in the interactions present in the crystal packing, from predominant π–π stacking in 1 to exclusively C—H...O/N interactions (Caryl—H...Ocarbonyl, C—H...Omethoxy and Caryl—H...Npyridine) in 3. |
| first_indexed | 2024-04-10T05:18:02Z |
| format | Article |
| id | doaj.art-58648ae1d4094bd08ab375db24253923 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-10T05:18:02Z |
| publishDate | 2023-03-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-58648ae1d4094bd08ab375db242539232023-03-08T12:49:03ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902023-03-0179315716210.1107/S2056989023001056yz2028Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrrolesHarry C. Sample0Brendan Twamley1Mathias O. Senge2School of Chemistry, Chair of Organic Chemistry, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, D02 R590, Dublin, IrelandSchool of Chemistry, Trinity College Dublin, College Green, Dublin 2, IrelandSchool of Chemistry, Chair of Organic Chemistry, Trinity Biomedical Sciences Institute, Trinity College Dublin, 152-160 Pearse St, D02 R590, Dublin, IrelandThe crystal structures of three S-(pyridin-2-yl) benzothioesters with varying para-phenyl substituents are presented, namely, S-(pyridin-2-yl) 4-nitrobenzothioate (1, C12H8N2O3S), S-(pyridin-2-yl) 4-methylbenzothioate (2, C13H11NO2S) and S-(pyridin-2-yl) 4-methoxybenzothioate (3, C13H11NO2S). This class of compounds are used in the mono-acylation of pyrrolic species to yield multifunctional tetrapyrroles. The structures presented herein are the first of their compound class. The dominant interactions present in this series are π–π stacking and C—H...O interactions, and as the para-phenyl motif changes from electron withdrawing (NO2, 1) to electron donating (OCH3, 3), changes are observed in the interactions present in the crystal packing, from predominant π–π stacking in 1 to exclusively C—H...O/N interactions (Caryl—H...Ocarbonyl, C—H...Omethoxy and Caryl—H...Npyridine) in 3.http://scripts.iucr.org/cgi-bin/paper?S2056989023001056crystal structurebenzothioate derivativeshydrogen bondingπ–π-stacking |
| spellingShingle | Harry C. Sample Brendan Twamley Mathias O. Senge Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrroles Acta Crystallographica Section E: Crystallographic Communications crystal structure benzothioate derivatives hydrogen bonding π–π-stacking |
| title | Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrroles |
| title_full | Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrroles |
| title_fullStr | Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrroles |
| title_full_unstemmed | Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrroles |
| title_short | Structures of S-(pyridin-2-yl) 4-nitrobenzothioate, S-(pyridin-2-yl) 4-methylbenzothioate and S-(pyridin-2-yl) 4-methoxybenzothioate: building blocks for low-symmetry multifunctional tetrapyrroles |
| title_sort | structures of s pyridin 2 yl 4 nitrobenzothioate s pyridin 2 yl 4 methylbenzothioate and s pyridin 2 yl 4 methoxybenzothioate building blocks for low symmetry multifunctional tetrapyrroles |
| topic | crystal structure benzothioate derivatives hydrogen bonding π–π-stacking |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989023001056 |
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