{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,31]],"date-time":"2026-07-31T05:30:31Z","timestamp":1785475831578,"version":"3.56.0"},"reference-count":104,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2023,1,12]],"date-time":"2023-01-12T00:00:00Z","timestamp":1673481600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"General Chemistry research group"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The halogen bond complexes CF3X\u22efY and C2F3X\u22efY, with Y = furan, thiophene, selenophene and X = Cl, Br, I, have been studied by using DFT and CCSD(T) in order to understand which factors govern the interaction between the halogen atom X and the aromatic ring. We found that PBE0-dDsC\/QZ4P gives an adequate description of the interaction energies in these complexes, compared to CCSD(T) and experimental results. The interaction between the halogen atom X and the \u03c0-bonds in perpendicular orientation is stronger than the interaction with the in-plane lone pairs of the heteroatom of the aromatic cycle. The strength of the interaction follows the trend Cl &lt; Br &lt; I; the chalcogenide in the aromatic ring nor the hybridization of the C\u2013X bond play a decisive role. The energy decomposition analysis shows that the interaction energy is dominated by all three contributions, viz., the electrostatic, orbital, and dispersion interactions: not one factor dominates the interaction energy. The aromaticity of the ring is undisturbed upon halogen bond formation: the \u03c0-ring current remains equally strong and diatropic in the complex as it is for the free aromatic ring. However, the spin-orbit coupling between the singlet and triplet \u03c0\u2192\u03c0* states is increased upon halogen bond formation and a faster intersystem crossing between these states is therefore expected.<\/jats:p>","DOI":"10.3390\/molecules28020772","type":"journal-article","created":{"date-parts":[[2023,1,12]],"date-time":"2023-01-12T05:45:33Z","timestamp":1673502333000},"page":"772","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["The Halogen Bond in Weakly Bonded Complexes and the Consequences for Aromaticity and Spin-Orbit Coupling"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8996-2860","authenticated-orcid":false,"given":"Ana V.","family":"Cunha","sequence":"first","affiliation":[{"name":"MolSpec, Departement Chemie, Universiteit Antwerpen, Groenenborgerlaan 171, 2020 Antwerpen, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0038-6030","authenticated-orcid":false,"given":"Remco W. A.","family":"Havenith","sequence":"additional","affiliation":[{"name":"Stratingh Institute for Chemistry and Zernike Institute for Advanced Materials, Rijksuniversiteit Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands"},{"name":"Gent Quantum Chemistry Group, Faculteit Wetenschappen, Universiteit Gent, Krijgslaan 281 (S3), 9000 Gent, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jari","family":"van Gog","sequence":"additional","affiliation":[{"name":"MolSpec, Departement Chemie, Universiteit Antwerpen, Groenenborgerlaan 171, 2020 Antwerpen, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0563-1509","authenticated-orcid":false,"given":"Freija","family":"De Vleeschouwer","sequence":"additional","affiliation":[{"name":"Algemene Chemie (ALGC), Vrije Universiteit Brussel (VUB), Pleinlaan 2, 1050 Brussel, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Frank","family":"De Proft","sequence":"additional","affiliation":[{"name":"Algemene Chemie (ALGC), Vrije Universiteit Brussel (VUB), Pleinlaan 2, 1050 Brussel, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3167-8944","authenticated-orcid":false,"given":"Wouter","family":"Herrebout","sequence":"additional","affiliation":[{"name":"MolSpec, Departement Chemie, Universiteit Antwerpen, Groenenborgerlaan 171, 2020 Antwerpen, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1711","DOI":"10.1351\/PAC-REC-12-05-10","article-title":"Definition of the Halogen Bond (IUPAC Recommendations 2013)","volume":"85","author":"Desiraju","year":"2013","journal-title":"Pure Appl. 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