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Two types of halonium cation monomers, namely the iodonium ion of adamantylideneadamantane and ethynyl(phenyl)\u2010\u03bb\n                    <jats:sup>3<\/jats:sup>\n                    \u2010iodane, along with their chlorine and bromine analogues, are examined. Complexes formed with HCN molecules are investigated using quantum chemical calculations and topological analyses of electron density. The findings indicate that the \u03c3\u2010hole plays a decisive role in directing both the geometry and strength of these noncovalent interactions. Systems featuring a single \u03c3\u2010hole exhibit reduced stabilization upon additional ligand coordination, often weakening the primary halogen bond. In contrast, cations with two \u03c3\u2010holes can accommodate up to three or four HCN molecules without compromising the integrity of the original halogen bonds. Nevertheless, the most favorable configuration remains the directional binding of two ligands to two distinct \u03c3\u2010holes.\n                  <\/jats:p>","DOI":"10.1002\/cphc.202500357","type":"journal-article","created":{"date-parts":[[2025,9,1]],"date-time":"2025-09-01T23:02:17Z","timestamp":1756767737000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Does the Presence of Sigma Holes Affect the Way Neutral Ligands Attach to a Halonium Cation?"],"prefix":"10.1002","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6495-6963","authenticated-orcid":false,"given":"Mariusz","family":"Michalczyk","sequence":"first","affiliation":[{"name":"Faculty of Chemistry Wroclaw University of Science and Technology  Wybrzeze Wyspianskiego 27 50\u2010370 Wroclaw Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,9]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"crossref","DOI":"10.1093\/acprof:oso\/9780199558964.001.0001","volume-title":"The Nature of the Hydrogen Bond: Outline of a Comprehensive Hydrogen Bond Theory","author":"Gilli G.","year":"2009"},{"key":"e_1_2_8_3_1","unstructured":"G. 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