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Square-pyramidal pentavalent halogen-containing molecules, including X-Cl-F4, F-Y-F4, and F-I-X4 compounds (where X = F, Cl, Br, and I and Y = Cl, Br, and I) were employed as \u03c3-hole\/lp donors. On the other hand, benzene (BZN) and hexafluorobenzene (HFB) were chosen as electron-rich and electron-deficient aromatic \u03c0-systems, respectively. The investigation relied upon a variety of quantum chemical calculations that complement each other. The results showed that (i) the binding energy of the X-Y-F4\u00b7\u00b7\u00b7BZN complexes increased (i.e., more negative) as the Y atom had a larger magnitude of \u03c3-hole, contrary to the pattern of X-Y-F4\u00b7\u00b7\u00b7HFB complexes; (ii) the interaction energies of X-Y-F4\u00b7\u00b7\u00b7BZN complexes were dominated by both dispersion and electrostatic contributions, while dispersive interactions dominated X-Y-F4\u00b7\u00b7\u00b7HFB complexes; and (iii) the X4 atoms in F-I-X4\u00b7\u00b7\u00b7\u03c0-system complexes governed the interaction energy pattern: the larger the X4 atoms were, the greater the interaction energies were, for the same \u03c0-system. The results had illuminating facets in regard to the rarely addressed cases of the \u03c3-hole\/lp contradictory scene.<\/jats:p>","DOI":"10.1021\/acsomega.0c05795","type":"journal-article","created":{"date-parts":[[2021,1,25]],"date-time":"2021-01-25T00:45:44Z","timestamp":1611535544000},"page":"3319-3329","source":"Crossref","is-referenced-by-count":17,"title":["Cospatial \u03c3-Hole and Lone Pair Interactions\nof Square-Pyramidal Pentavalent Halogen Compounds with \u03c0-Systems:\nA Quantum Mechanical Study"],"prefix":"10.1021","volume":"6","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4819-2040","authenticated-orcid":true,"given":"Mahmoud A. A.","family":"Ibrahim","sequence":"first","affiliation":[{"name":"Minia University , , ,","place":["Minia, Egypt, 61519"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ossama A. M.","family":"Ahmed","sequence":"additional","affiliation":[{"name":"Minia University , , ,","place":["Minia, Egypt, 61519"]},{"name":"Cairo University , , ,","place":["Giza, Egypt, 12613"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sabry","family":"El-Taher","sequence":"additional","affiliation":[{"name":"Cairo University , , ,","place":["Giza, Egypt, 12613"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jabir H.","family":"Al-Fahemi","sequence":"additional","affiliation":[{"name":"Umm Al-Qura University , , ,","place":["Makkah, Saudi Arabia, 21955"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3712-7710","authenticated-orcid":true,"given":"Nayra A. 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