{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,22]],"date-time":"2026-06-22T13:39:59Z","timestamp":1782135599915,"version":"3.54.5"},"reference-count":96,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T00:00:00Z","timestamp":1693180800000},"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":["22-23-00307"],"award-info":[{"award-number":["22-23-00307"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>2,3,5,6-Tetramethyl-1,4-diisocyanobenzene (1), 1,4-diisocyanobenzene (2), and 1,4-dicyanobenzene (3) were co-crystallized with 1,3,5-triiodotrifluorobenzene (1,3,5-FIB) to give three cocrystals, 1\u00b71,3,5-FIB, 2\u00b72(1,3,5-FIB), and 3\u00b72(1,3,5-FIB), which were studied by X-ray diffraction. A common feature of the three structures is the presence of I\u00b7\u00b7\u00b7Cisocyanide or I\u00b7\u00b7\u00b7Nnitrile halogen bonds (HaBs), which occurs between an iodine \u03c3-hole and the isocyanide C-(or the nitrile N-) atom. The diisocyanide and dinitrile cocrystals 2\u00b72(1,3,5-FIB) and 3\u00b72(1,3,5-FIB) are isostructural, thus providing a basis for accurate comparison of the two types of noncovalent linkages of C\u2261N\/N\u2261C groups in the composition of structurally similar entities and in one crystal environment. The bonding situation was studied by a set of theoretical methods. Diisocyanides are more nucleophilic than the dinitrile and they exhibit stronger binding to 1,3,5-FIB. In all structures, the HaBs are mostly determined by the electrostatic interactions, but the dispersion and induction components also provide a noticeable contribution and make the HaBs attractive. Charge transfer has a small contribution (&lt;5%) to the HaB and it is higher for the diisocyanide than for the dinitrile systems. At the same time, diisocyanide and dinitrile structures exhibit typical electron-donor and \u03c0-acceptor properties in relation to the HaB donor.<\/jats:p>","DOI":"10.3390\/ijms241713324","type":"journal-article","created":{"date-parts":[[2023,8,28]],"date-time":"2023-08-28T05:46:47Z","timestamp":1693201607000},"page":"13324","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Halogen Bonding Involving Isomeric Isocyanide\/Nitrile Groups"],"prefix":"10.3390","volume":"24","author":[{"given":"Andrey S.","family":"Smirnov","sequence":"first","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4485-7247","authenticated-orcid":false,"given":"Eugene A.","family":"Katlenok","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6471-5158","authenticated-orcid":false,"given":"Alexander S.","family":"Mikherdov","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mariya A.","family":"Kryukova","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8692-9627","authenticated-orcid":false,"given":"Nadezhda A.","family":"Bokach","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2253-085X","authenticated-orcid":false,"given":"Vadim Yu.","family":"Kukushkin","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7\/9, 199034 Saint Petersburg, Russia"},{"name":"Laboratory of Crystal Engineering of Functional Materials, South Ural State University, 76, Lenin Av., 454080 Chelyabinsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,8,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3828","DOI":"10.1021\/acs.accounts.1c00393","article-title":"Noncovalent Interactions in Organometallic Chemistry: From Cohesion to Reactivity, a New Chapter","volume":"54","author":"Cornaton","year":"2021","journal-title":"Acc. 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