{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,23]],"date-time":"2026-04-23T08:41:25Z","timestamp":1776933685540,"version":"3.51.2"},"reference-count":70,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2025,2,11]],"date-time":"2025-02-11T00:00:00Z","timestamp":1739232000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministry of Science and Higher Education of the Russian Federation","award":["075-00276-25-00"],"award-info":[{"award-number":["075-00276-25-00"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The addition reactions of water, alcohols, and primary and secondary amines to the 10-acetonitrilium derivative of nido-carborane were studied. Hydrolysis of 10-MeC\u2261N-7,8-C2B9H11 results in iminol 10-MeC(OH)=HN-7,8-C2B9H11, which, on treatment with a base, gives amide [10-MeC(=O)HN-7,8-C2B9H11]\u2212. The reactions of 10-MeC\u2261N-7,8-C2B9H11 with alcohols lead to imidates 10-ROC(Me)=HN-7,8-C2B9H11 (R = Me, Et) as mixtures of E- and Z-isomers. In the solid state, 10-MeOC(Me)=HN-7,8-C2B9H11 adopts E-configuration. The reactions of 10-MeC\u2261N-7,8-C2B9H11 with primary amines result in amidines 10-RNHC(Me)=HN-7,8-C2B9H11 (R = Me, Et) as mixtures of E- and Z-isomers. In the solid state 10-EtNHC(Me)=HN-7,8-C2B9H11 was found to have the Z-configuration, which is stabilized by intramolecular N-H\u22efH-B interactions between the NH group originating from the primary amine and the BH group of the carborane cage. These interactions are rather strong (3.7 kcal\/mol) and are likely to persist in solution. The reactions of 10-MeC\u2261N-7,8-C2B9H11 with secondary acyclic (Me2NH, Et2NH) and cyclic (piperidine, morpholine) amines result in amidines 10-R2NC(Me)=HN-7,8-C2B9H11 (R = Me, Et; R2 = N(CH2)5, N(CH2CH2)2O) as single isomers, which, according to single crystal X-ray diffraction data, have the E-configuration.<\/jats:p>","DOI":"10.3390\/molecules30040828","type":"journal-article","created":{"date-parts":[[2025,2,12]],"date-time":"2025-02-12T12:12:16Z","timestamp":1739362336000},"page":"828","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Nucleophilic Addition Reactions to 10-Acetonitrilium Derivative of nido-Carborane and Intramolecular NH\u22efHB Interactions in N-Alkyl Amidines 10-RNHC(Me)=NH-7,8-C2B9H11"],"prefix":"10.3390","volume":"30","author":[{"given":"Kirill R.","family":"Pakholkov","sequence":"first","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3311-4365","authenticated-orcid":false,"given":"Ekaterina V.","family":"Bogdanova","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5671-4086","authenticated-orcid":false,"given":"Marina Yu.","family":"Stogniy","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0617-0118","authenticated-orcid":false,"given":"Kyrill Yu.","family":"Suponitsky","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6386-7301","authenticated-orcid":false,"given":"Sergey A.","family":"Anufriev","sequence":"additional","affiliation":[{"name":"A.N. 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