{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,27]],"date-time":"2026-10-27T11:35:09Z","timestamp":1793100909763,"version":"4.5.0"},"reference-count":20,"publisher":"International Union of Crystallography (IUCr)","issue":"10","license":[{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"Studienstiftung des deutschen Volkes","id":[{"id":"https:\/\/ror.org\/05xwwfy96","id-type":"ROR","asserted-by":"crossref"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2026,9,11]]},"published-print":{"date-parts":[[2026,10,1]]},"abstract":"<jats:p>\n                    The BBr\n                    <jats:sub>3<\/jats:sub>\n                    -promoted demethylation of 3-(methoxymethyl)-6-phenyl-1,2,4,5-tetrazine, C\n                    <jats:sub>10<\/jats:sub>\n                    H\n                    <jats:sub>10<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O, resulted in the alcohol (6-phenyl-1,2,4,5-tetrazin-3-yl)methanol, C\n                    <jats:sub>9<\/jats:sub>\n                    H\n                    <jats:sub>8<\/jats:sub>\n                    N\n                    <jats:sub>4<\/jats:sub>\n                    O, and the bromide 3-(bromomethyl)-6-phenyl-1,2,4,5-tetrazine, C\n                    <jats:sub>9<\/jats:sub>\n                    H\n                    <jats:sub>7<\/jats:sub>\n                    BrN\n                    <jats:sub>4<\/jats:sub>\n                    . All three compounds were analysed by nuclear magnetic resonance (NMR) spectroscopy in solution and by single-crystal X-ray diffraction using non-spherical scattering factors for structure refinement. The substrate as well as the corresponding bromide form \u03c0\u2013\u03c0 interactions between antiparallel stacks of molecules. In contrast, due to the intermolecular hydrogen bonds present, which lead to the formation of a bent dimer, the alcohol forms only very weak parallel \u03c0\u2013\u03c0 stacks. Corresponding O\u2014H...N hydrogen bonds are established between the hydroxy group and an N atom of a neighbouring tetrazine molecule, an only rarely explored structural feature of 1,2,4,5-tetrazines.\n                  <\/jats:p>","DOI":"10.1107\/s2056989026009527","type":"journal-article","created":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T15:36:31Z","timestamp":1789400191000},"page":"1221-1225","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structures of products from the BBr\n                    <sub>3<\/sub>\n                    -promoted demethylation of 3-(methoxymethyl)-6-phenyl-1,2,4,5-tetrazine"],"prefix":"10.1107","volume":"82","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4823-8646","authenticated-orcid":true,"given":"Jona","family":"Voss","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1485-757X","authenticated-orcid":true,"given":"Jan-Hendrik","family":"Lamm","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2026,9,30]]},"reference":[{"key":"wm5811_bb1","doi-asserted-by":"crossref","first-page":"1405","DOI":"10.1021\/acs.bioconjchem.9b00157","volume":"30","author":"Baalmann","year":"2019","journal-title":"Bioconjugate Chem."},{"key":"wm5811_bb2","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1107\/S2053273314022207","volume":"71","author":"Bourhis","year":"2015","journal-title":"Acta Cryst. A"},{"key":"wm5811_bb3","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Cryst."},{"key":"wm5811_bb4","doi-asserted-by":"crossref","first-page":"2176","DOI":"10.1021\/om100106e","volume":"29","author":"Fulmer","year":"2010","journal-title":"Organometallics"},{"key":"wm5811_bb5","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Cryst. B"},{"key":"wm5811_bb6","doi-asserted-by":"crossref","first-page":"1745","DOI":"10.1002\/jhet.5570450628","volume":"45","author":"Hu","year":"2008","journal-title":"J. Heterocycl. Chem."},{"key":"wm5811_bb7","doi-asserted-by":"crossref","first-page":"1371","DOI":"10.1021\/ci500183u","volume":"54","author":"Huber","year":"2014","journal-title":"J. Chem. Inf. Model."},{"key":"wm5811_bb8","doi-asserted-by":"crossref","first-page":"1675","DOI":"10.1039\/D0SC05526C","volume":"12","author":"Kleemiss","year":"2021","journal-title":"Chem. Sci."},{"key":"wm5811_bb9","doi-asserted-by":"crossref","first-page":"1143","DOI":"10.1002\/jhet.5570120612","volume":"12","author":"Lang","year":"1975","journal-title":"J. Heterocycl. Chem."},{"key":"wm5811_bb10","doi-asserted-by":"crossref","unstructured":"Neese, F. (2022). WIREs Comput. Mol. Sci. 12, e1606.","DOI":"10.1002\/wcms.1606"},{"key":"wm5811_bb11","doi-asserted-by":"crossref","first-page":"2126","DOI":"10.1002\/cber.189302602188","volume":"26","author":"Pinner","year":"1893","journal-title":"Ber. Dtsch. Chem. Ges."},{"key":"wm5811_bb12","unstructured":"Rigaku OD (2025). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England."},{"key":"wm5811_bb13","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. A"},{"key":"wm5811_bb14","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1039\/C9SC04649F","volume":"11","author":"Tu","year":"2020","journal-title":"Chem. Sci."},{"key":"wm5811_bb15","doi-asserted-by":"crossref","first-page":"164","DOI":"10.1107\/S2056989025000441","volume":"81","author":"Voss","year":"2025","journal-title":"Acta Cryst. E"},{"key":"wm5811_bb16","doi-asserted-by":"crossref","first-page":"5293","DOI":"10.1021\/acs.orglett.2c01873","volume":"24","author":"Wang","year":"2022","journal-title":"Org. Lett."},{"key":"wm5811_bb17","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1107\/S0021889810022120","volume":"43","author":"Westrip","year":"2010","journal-title":"J. Appl. Cryst."},{"key":"wm5811_bb18","doi-asserted-by":"crossref","first-page":"o2397","DOI":"10.1107\/S1600536807017175","volume":"63","author":"Xu","year":"2007","journal-title":"Acta Cryst. E"},{"key":"wm5811_bb19","doi-asserted-by":"crossref","first-page":"e71028","DOI":"10.1002\/chem.71028","volume":"32","author":"Yim","year":"2026","journal-title":"Chem. Eur. J."},{"key":"wm5811_bb20","doi-asserted-by":"crossref","first-page":"1055823","DOI":"10.3389\/fmolb.2022.1055823","volume":"9","author":"Zhao","year":"2022","journal-title":"Front. Mol. Biosci."}],"container-title":["Acta Crystallographica Section E Crystallographic Communications"],"original-title":[],"link":[{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/10\/00\/wm5811\/wm5811.pdf","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/journals.iucr.org\/e\/issues\/2026\/10\/00\/wm5811\/wm5811.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,27]],"date-time":"2026-10-27T11:07:57Z","timestamp":1793099277000},"score":1,"resource":{"primary":{"URL":"https:\/\/journals.iucr.org\/paper?S2056989026009527"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,30]]},"references-count":20,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2026,10]]}},"alternative-id":["S2056989026009527"],"URL":"https:\/\/doi.org\/10.1107\/s2056989026009527","relation":{"is-supplemented-by":[{"id-type":"doi","id":"10.1107\/S2056989026009527\/wm5811sup1.cif","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026009527\/wm58111sup2.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026009527\/wm58112sup3.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026009527\/wm58113sup4.hkl","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026009527\/wm58111sup5.cml","asserted-by":"subject"},{"id-type":"doi","id":"10.1107\/S2056989026009527\/wm58112sup6.cml","asserted-by":"subject"}]},"ISSN":["2056-9890"],"issn-type":[{"value":"2056-9890","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,30]]},"assertion":[{"value":"Acta Crystallographica Section E: Crystallographic Communications","order":0,"name":"journal","label":"Publication","explanation":{"URL":"https:\/\/journals.iucr.org\/e"},"group":{"name":"general","label":"General"}},{"value":"research communications","order":1,"name":"content_type","label":"Content type","explanation":{"URL":"https:\/\/journals.iucr.org\/e\/services\/notesforauthors.html"},"group":{"name":"general","label":"General"}},{"value":"Available","URL":"https:\/\/scripts.iucr.org\/cgi-bin\/citedin?wm5811","order":2,"name":"article_metrics","label":"Article metrics","group":{"name":"general","label":"General"}},{"value":"Yes","order":0,"name":"peer_reviewed","label":"Peer reviewed","group":{"name":"peer_review","label":"Peer review"}},{"value":"Single blind","order":1,"name":"review_process","label":"Review process","group":{"name":"peer_review","label":"Peer review"}},{"value":"7 August 2026","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication history"}},{"value":"11 September 2026","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication history"}},{"value":"30 September 2026","order":2,"name":"published_online","label":"Published online","group":{"name":"publication_history","label":"Publication history"}},{"value":"This article has supporting information","name":"supplementary_materials","label":"Supplementary materials","explanation":{"URL":"https:\/\/scripts.iucr.org\/cgi-bin\/sendsup?wm5811"}},{"value":"\u00a9 2026 Voss and Lamm","order":0,"name":"copyright","label":"Copyright","explanation":{"URL":"https:\/\/journals.iucr.org\/services\/copyrightpolicy.html"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}},{"value":"Creative Commons Attribution (CC-BY)","order":1,"name":"license","label":"Licence","explanation":{"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},"group":{"name":"copyright_and_licencing","label":"Copyright and licencing"}}]}}