{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:48:12Z","timestamp":1760147292536,"version":"build-2065373602"},"reference-count":37,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2023,1,23]],"date-time":"2023-01-23T00:00:00Z","timestamp":1674432000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"The Ministry of Science and Higher Education of the Russian Federation","award":["1021052806375-6-1.4.3"],"award-info":[{"award-number":["1021052806375-6-1.4.3"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>X-ray diffraction analysis and IR spectroscopy were used to study the products of the interaction of vinyl cations C3H5+ and C4H7+ (Cat+) (as salts of carborane anion CHB11Cl11\u2212) with basic molecules of water, alcohols, and acetone that can crystallize from solutions in dichloromethane and C6HF5. Interaction with water, as content increased, proceeded via three-stages. (1) adduct Cat+\u00b7OH2 forms in which H2O binds (through the O atom) to the C=C+ bond of the cation with the same strength as seen in the binding to Na in Na(H2O)6+. (2) H+ is transferred from cation Cat+\u00b7OH2 to a water molecule forming H3O+ and alcohol molecules (L) having the CH=CHOH entity. The O- atom of alcohols is attached to the H atom of the C=C+-H moiety of Cat+ thereby forming a very strong asymmetric H\u2013bond, (C=)C+-H\u22c5\u22c5\u22c5O. (3) Finally all vinyl cations are converted into alcohol molecule L and H3O+ cations, yielding proton disolvates L-H+-L with a symmetric very strong H-bond. When an acetone molecule (Ac) interacts with Cat+, H+ is transferred to Ac giving rise to a reactive carbene and proton disolvate Ac-H+-Ac. Thus, the alleged high reactivity of vinyl cations seems to be an exaggeration.<\/jats:p>","DOI":"10.3390\/molecules28031146","type":"journal-article","created":{"date-parts":[[2023,1,24]],"date-time":"2023-01-24T01:29:45Z","timestamp":1674523785000},"page":"1146","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Interaction of Vinyl-Type Carbocations, C3H5+ and C4H7+ with Molecules of Water, Alcohols, and Acetone"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6596-9590","authenticated-orcid":false,"given":"Evgenii S.","family":"Stoyanov","sequence":"first","affiliation":[{"name":"N.N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Irina Yu.","family":"Bagryanskaya","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Irina V.","family":"Stoyanova","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, 630090 Novosibirsk, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,23]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1002\/anie.197301731","article-title":"Carbocations and Electrophilic Reactions","volume":"12","author":"Olah","year":"1973","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Olah, G.A., and Prakash, G.K.S. (2004). 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