Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate
An orthogonally addressable 3,6-disubstituted 1,2,4,5-tetrazine, namely 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate (C14H14Cl3N5O3), was synthesized and characterized by single-crystal X-ray diffraction. The tetrazine comprises a free hydroxyl and a 2,2,2-tri...
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International Union of Crystallography
2025-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S2056989025000441 |
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| author | J. Voss H.G. Stammler N. Sewald |
| author_facet | J. Voss H.G. Stammler N. Sewald |
| author_sort | J. Voss |
| collection | DOAJ |
| description | An orthogonally addressable 3,6-disubstituted 1,2,4,5-tetrazine, namely 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate (C14H14Cl3N5O3), was synthesized and characterized by single-crystal X-ray diffraction. The tetrazine comprises a free hydroxyl and a 2,2,2-trichloroethoxycarbonyl protected amino group, which gives rise to hydrogen-bonding interactions each making the tetrazine highly linked in the solid state. The carbamate moieties form intermolecular hydrogen bonds, stacking the tetrazine molecules above each other, while lateral hydrogen bonds are formed between a tetrazine N atom and a hydroxyl group, the latter interaction being a scarcely explored structural feature of 1,2,4,5-tetrazines. |
| format | Article |
| id | doaj-art-5e3c314d076a45c7a3dbbb2aebdc0fb9 |
| institution | Kabale University |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-5e3c314d076a45c7a3dbbb2aebdc0fb92025-02-06T07:27:16ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-02-0181216416810.1107/S2056989025000441dj2079Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamateJ. Voss0H.G. Stammler1N. Sewald2Bielefeld University, Department of Chemistry, Universitaetsstr. 25, Bielefeld, 33615, GermanyBielefeld University, Department of Chemistry, Universitaetsstr. 25, Bielefeld, 33615, GermanyBielefeld University, Department of Chemistry, Universitaetsstr. 25, Bielefeld, 33615, GermanyAn orthogonally addressable 3,6-disubstituted 1,2,4,5-tetrazine, namely 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate (C14H14Cl3N5O3), was synthesized and characterized by single-crystal X-ray diffraction. The tetrazine comprises a free hydroxyl and a 2,2,2-trichloroethoxycarbonyl protected amino group, which gives rise to hydrogen-bonding interactions each making the tetrazine highly linked in the solid state. The carbamate moieties form intermolecular hydrogen bonds, stacking the tetrazine molecules above each other, while lateral hydrogen bonds are formed between a tetrazine N atom and a hydroxyl group, the latter interaction being a scarcely explored structural feature of 1,2,4,5-tetrazines.https://journals.iucr.org/paper?S2056989025000441crystal structure1,2,4,5-tetrazinecarbamate |
| spellingShingle | J. Voss H.G. Stammler N. Sewald Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate Acta Crystallographica Section E: Crystallographic Communications crystal structure 1,2,4,5-tetrazine carbamate |
| title | Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate |
| title_full | Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate |
| title_fullStr | Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate |
| title_full_unstemmed | Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate |
| title_short | Synthesis and crystal structure of 2,2,2-trichloroethyl N-{4-[6-(1-hydroxyethyl)-1,2,4,5-tetrazin-3-yl]benzyl}carbamate |
| title_sort | synthesis and crystal structure of 2 2 2 trichloroethyl n 4 6 1 hydroxyethyl 1 2 4 5 tetrazin 3 yl benzyl carbamate |
| topic | crystal structure 1,2,4,5-tetrazine carbamate |
| url | https://journals.iucr.org/paper?S2056989025000441 |
| work_keys_str_mv | AT jvoss synthesisandcrystalstructureof222trichloroethyln461hydroxyethyl1245tetrazin3ylbenzylcarbamate AT hgstammler synthesisandcrystalstructureof222trichloroethyln461hydroxyethyl1245tetrazin3ylbenzylcarbamate AT nsewald synthesisandcrystalstructureof222trichloroethyln461hydroxyethyl1245tetrazin3ylbenzylcarbamate |