{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,3]],"date-time":"2026-07-03T23:40:31Z","timestamp":1783122031932,"version":"3.54.6"},"reference-count":85,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2024,11,28]],"date-time":"2024-11-28T00:00:00Z","timestamp":1732752000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["22-73-10007"],"award-info":[{"award-number":["22-73-10007"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Herein, we describe a novel coupling between ambiphilic 2-pyridylselenyl reagents and nitriles featuring an active \u03b1-methylene group. Depending on the solvent employed, this reaction can yield two distinct types of cationic pyridinium-fused selenium-containing heterocycles, 1,3-selenazolium or 1,2,4-selenadiazolium salts, in high yields. This is in contrast to what we observed before for other nitriles. Notably, the formation of selenadiazolium is reversible, gradually converting into the more thermodynamically stable selenazolium product in solution. Our findings reveal, for the first time, the reversible nature of 1,3-dipolar cyclization between the CN triple bond and 2-pyridylselenyl reagents. Nitrile substitution experiments in the adducts confirmed the dynamic nature of this cyclization, indicating potential applications in dynamic covalent chemistry. DFT calculations revealed the mechanistic pathways for new cyclizations, suggesting a concerted [3 + 2] cycloaddition for the formation of selenadiazolium rings and a stepwise mechanism involving a ketenimine intermediate for the formation of selenazolium rings. Natural bond orbital analysis confirmed the involvement of \u03c3-hole interactions and lone pair to \u03c3* electron donation in these processes. Additionally, theoretical investigations of \u03c3-hole interactions were performed, focusing on the selenium-centered contacts within the new compounds.<\/jats:p>","DOI":"10.3390\/ijms252312798","type":"journal-article","created":{"date-parts":[[2024,11,28]],"date-time":"2024-11-28T05:19:39Z","timestamp":1732771179000},"page":"12798","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Diverse Cyclization Pathways Between Nitriles with Active \u03b1-Methylene Group and Ambiphilic 2-Pyridylselenyl Reagents Enabled by Reversible Covalent Bonding"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4167-7478","authenticated-orcid":false,"given":"Alexey A.","family":"Artemjev","sequence":"first","affiliation":[{"name":"Research Institute of Chemistry, Peoples\u2019 Friendship University of Russia, 6 Miklukho-Maklaya Street, 117198 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander A.","family":"Sapronov","sequence":"additional","affiliation":[{"name":"Research Institute of Chemistry, Peoples\u2019 Friendship University of Russia, 6 Miklukho-Maklaya Street, 117198 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0156-5535","authenticated-orcid":false,"given":"Alexey S.","family":"Kubasov","sequence":"additional","affiliation":[{"name":"Kurnakov Institute of General and Inorganic Chemistry, 31 Leninsky Prospekt, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander S.","family":"Peregudov","sequence":"additional","affiliation":[{"name":"Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 119334 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9913-5324","authenticated-orcid":false,"given":"Alexander S.","family":"Novikov","sequence":"additional","affiliation":[{"name":"Research Institute of Chemistry, Peoples\u2019 Friendship University of Russia, 6 Miklukho-Maklaya Street, 117198 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6006-6883","authenticated-orcid":false,"given":"Anton R.","family":"Egorov","sequence":"additional","affiliation":[{"name":"Research Institute of Chemistry, Peoples\u2019 Friendship University of Russia, 6 Miklukho-Maklaya Street, 117198 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8806-2975","authenticated-orcid":false,"given":"Victor N.","family":"Khrustalev","sequence":"additional","affiliation":[{"name":"Research Institute of Chemistry, Peoples\u2019 Friendship University of Russia, 6 Miklukho-Maklaya Street, 117198 Moscow, Russia"},{"name":"N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt 47, 119334 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1765-5241","authenticated-orcid":false,"given":"Alexander V.","family":"Borisov","sequence":"additional","affiliation":[{"name":"Department of Chemistry, R.E. Alekseev Nizhny Novgorod State Technical University, Minin Street, 24, 603155 Nizhny Novgorod, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0858-5897","authenticated-orcid":false,"given":"Zhanna V.","family":"Matsulevich","sequence":"additional","affiliation":[{"name":"Department of Chemistry, R.E. Alekseev Nizhny Novgorod State Technical University, Minin Street, 24, 603155 Nizhny Novgorod, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Namiq G.","family":"Shikhaliyev","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering, Baku Engineering University, Hasan Aliyev Street 120, Baku AZ0101, Azerbaijan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9162-5169","authenticated-orcid":false,"given":"Valentine G.","family":"Nenajdenko","sequence":"additional","affiliation":[{"name":"Department of Chemistry, M.V. 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