{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T02:43:34Z","timestamp":1760150614433,"version":"build-2065373602"},"reference-count":46,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2023,12,18]],"date-time":"2023-12-18T00:00:00Z","timestamp":1702857600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100002301","name":"Estonian Research Council","doi-asserted-by":"publisher","award":["PRG 1736"],"award-info":[{"award-number":["PRG 1736"]}],"id":[{"id":"10.13039\/501100002301","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Acid-base properties are the simplest expression of compounds\u2019 coordinating ability. In the present work, we studied in silico how the gas-phase Br\u00f8nsted acidity (GA) of several polycyano-substituted compounds change when cyano (CN) groups are replaced by 1,2,2-tricyanovinyl (TCNV) groups in (iso)cyanic acid, dicyanoamine, cyanoform, and hydrogen tetracyanoborate. Different tautomers and conformers\/isomers are included in this study. Gas-phase acidity values are compared with the acidities of various acids, including percyanated protonated monocarba-closo-dodecaborate (carborane acid) and dodecaborate, as well as hydrogen cyanide and 1,2,2-tricyanoethene. An estimation of acetonitrile (MeCN), dimethylsufoxide (DMSO), and 1,2-dichloroethane (DCE) acidities is presented using the COSMO-RS method and correlation analysis. The strongest acid with four TCNV groups shows remarkable acidic properties.<\/jats:p>","DOI":"10.3390\/molecules28248157","type":"journal-article","created":{"date-parts":[[2023,12,19]],"date-time":"2023-12-19T06:03:11Z","timestamp":1702965791000},"page":"8157","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Step-by-Step Replacement of Cyano Groups by Tricyanovinyls\u2014The Influence on the Acidity"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1869-0383","authenticated-orcid":false,"given":"Agnes","family":"K\u00fctt","sequence":"first","affiliation":[{"name":"Institute of Chemistry, University of Tartu, Ravila 14A, 50411 Tartu, Estonia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,12,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Reichardt, C., and Welton, T. (2011). 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