{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:47:58Z","timestamp":1787028478345,"version":"build-2736575974"},"reference-count":76,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2022,3,14]],"date-time":"2022-03-14T00:00:00Z","timestamp":1647216000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006701","name":"Umm al-Qura University","doi-asserted-by":"publisher","award":["22UQU433174DSR06"],"award-info":[{"award-number":["22UQU433174DSR06"]}],"id":[{"id":"10.13039\/501100006701","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003009","name":"Science and Technology Development Fund","doi-asserted-by":"publisher","award":["5480"],"award-info":[{"award-number":["5480"]}],"id":[{"id":"10.13039\/501100003009","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003009","name":"Science and Technology Development Fund","doi-asserted-by":"publisher","award":["7972"],"award-info":[{"award-number":["7972"]}],"id":[{"id":"10.13039\/501100003009","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>In the current study, unexplored type IV halogen\u22efhalogen interaction was thoroughly elucidated, for the first time, and compared to the well-established types I\u2013III interactions by means of the second-order M\u00f8ller\u2013Plesset (MP2) method. For this aim, the halobenzene\u22efhalobenzene homodimers (where halogen = Cl, Br, and I) were designed into four different types, parodying the considered interactions. From the energetic perspective, the preference of scouted homodimers was ascribed to type II interactions (i.e., highest binding energy), whereas the lowest binding energies were discerned in type III interactions. Generally, binding energies of the studied interactions were observed to decline with the decrease in the \u03c3-hole size in the order, C6H5I\u22efIC6H5 &gt; C6H5Br\u22efBrC6H5 &gt; C6H5Cl\u22efClC6H5 homodimers and the reverse was noticed in the case of type IV interactions. Such peculiar observations were relevant to the ample contributions of negative-belt\u22efnegative-belt interactions within the C6H5Cl\u22efClC6H5 homodimer. Further, type IV torsional trans \u2192 cis interconversion of C6H5X\u22efXC6H5 homodimers was investigated to quantify the \u03c0\u22ef\u03c0 contributions into the total binding energies. Evidently, the energetic features illustrated the amelioration of the considered homodimers (i.e., more negative binding energy) along the prolonged scope of torsional trans \u2192 cis interconversion. In turn, these findings outlined the efficiency of the cis configuration over the trans analog. Generally, symmetry-adapted perturbation theory-based energy decomposition analysis (SAPT-EDA) demonstrated the predominance of all the scouted homodimers by the dispersion forces. The obtained results would be beneficial for the omnipresent studies relevant to the applications of halogen bonds in the fields of materials science and crystal engineering.<\/jats:p>","DOI":"10.3390\/ijms23063114","type":"journal-article","created":{"date-parts":[[2022,3,15]],"date-time":"2022-03-15T03:06:10Z","timestamp":1647313570000},"page":"3114","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":47,"title":["Type I\u2013IV Halogen\u22efHalogen Interactions: A Comparative Theoretical Study in Halobenzene\u22efHalobenzene Homodimers"],"prefix":"10.3390","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4819-2040","authenticated-orcid":false,"given":"Mahmoud A. 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I.","family":"Shehata","sequence":"additional","affiliation":[{"name":"Computational Chemistry Laboratory, Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Muhammad Naeem","family":"Ahmed","sequence":"additional","affiliation":[{"name":"Department of Chemistry, The University of Azad Jammu and Kashmir, Muzaffarabad 13100, Pakistan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3035-661X","authenticated-orcid":false,"given":"Ahmed M.","family":"Shawky","sequence":"additional","affiliation":[{"name":"Science and Technology Unit (STU), Umm Al-Qura University, Makkah 21955, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Manal M.","family":"Khowdiary","sequence":"additional","affiliation":[{"name":"Chemistry Department, Faculty of Applied Science, Umm Al-Qura University, Al-Lith Branch, Makkah 24211, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2546-8035","authenticated-orcid":false,"given":"Eslam B.","family":"Elkaeed","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Sciences, College of Pharmacy, AlMaarefa University, Riyadh 13713, Saudi Arabia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mahmoud E. S.","family":"Soliman","sequence":"additional","affiliation":[{"name":"Molecular Modelling and Drug Design Research Group, School of Health Sciences, University of KwaZulu-Natal, Westville, Durban 4000, South Africa"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3712-7710","authenticated-orcid":false,"given":"Nayra A. M.","family":"Moussa","sequence":"additional","affiliation":[{"name":"Computational Chemistry Laboratory, Chemistry Department, Faculty of Science, Minia University, Minia 61519, Egypt"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,3,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"5473","DOI":"10.1002\/ejoc.202000660","article-title":"\u03c3-Hole Interactions in Catalysis","volume":"2020","author":"Breugst","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"731","DOI":"10.1016\/j.chempr.2018.02.022","article-title":"Sigma-Hole Interactions in Anion Recognition","volume":"4","author":"Lim","year":"2018","journal-title":"Chem"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2540","DOI":"10.1002\/cphc.201800409","article-title":"Chalcogen Bonding in Protein-Ligand Complexes: PDB Survey and Quantum Mechanical Calculations","volume":"19","author":"Kriz","year":"2018","journal-title":"ChemPhysChem"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1002\/pro.2201","article-title":"Halogen bonding (X-bonding): A biological perspective","volume":"22","author":"Scholfield","year":"2013","journal-title":"Protein Sci."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"10121","DOI":"10.1039\/C7DT01685A","article-title":"Chalcogen bonding in synthesis, catalysis and design of materials","volume":"46","author":"Mahmudov","year":"2017","journal-title":"Dalton Trans."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"683","DOI":"10.1039\/C5CE02230D","article-title":"Halogen bonding in a multi-connected 1,2,2-triiodo-alkene involving geminal and\/or vicinal iodines: A crystallographic and DFT study","volume":"18","author":"Berger","year":"2016","journal-title":"CrystEngComm"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"4625","DOI":"10.1007\/s00894-012-1454-8","article-title":"Molecular mechanical perspective on halogen bonding","volume":"18","author":"Ibrahim","year":"2012","journal-title":"J. Mol. Model."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1039\/C7FD00076F","article-title":"Probing covalency in halogen bonds through donor K-edge X-ray absorption spectroscopy: Polyhalides as coordination complexes","volume":"203","author":"Mustoe","year":"2017","journal-title":"Faraday Discuss."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1007\/s00894-006-0130-2","article-title":"Halogen bonding: The sigma-hole","volume":"13","author":"Clark","year":"2007","journal-title":"J. Mol. Model."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2320","DOI":"10.1021\/ct300399y","article-title":"Influence of Hydrogen Bonds on the P...P Pnicogen Bond","volume":"8","author":"Alkorta","year":"2012","journal-title":"J. Chem. Theory Comput."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1642","DOI":"10.1021\/jp508270g","article-title":"Strength of the pnicogen bond in complexes involving group Va elements N, P, and As","volume":"119","author":"Setiawan","year":"2015","journal-title":"J. Phys. Chem. A"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"15160","DOI":"10.1021\/jacs.7b08511","article-title":"The Origin of Chalcogen-Bonding Interactions","volume":"139","author":"Pascoe","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"25476","DOI":"10.1021\/acsomega.1c03461","article-title":"Effect of external electric field on tetrel bonding interactions in (FTF3...FH) complexes (T = C, Si, Ge, and Sn)","volume":"6","author":"Ibrahim","year":"2021","journal-title":"ACS Omega"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"32166","DOI":"10.1039\/C7CP06793C","article-title":"The sigma-hole revisited","volume":"19","author":"Politzer","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"723","DOI":"10.1007\/s00894-008-0386-9","article-title":"Expansion of the sigma-hole concept","volume":"15","author":"Murray","year":"2009","journal-title":"J. Mol. Model."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"4511","DOI":"10.1021\/jm0490540","article-title":"Probing the subpockets of factor Xa reveals two binding modes for inhibitors based on a 2-carboxyindole scaffold: A study combining structure-activity relationship and X-ray crystallography","volume":"48","author":"Nazare","year":"2005","journal-title":"J. Med. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4543","DOI":"10.1039\/b926326h","article-title":"Nonbonding interactions of organic halogens in biological systems: Implications for drug discovery and biomolecular design","volume":"12","author":"Lu","year":"2010","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2344","DOI":"10.1021\/ci9002393","article-title":"Fluorine bonding\u2014How does it work in protein-ligand interactions?","volume":"49","author":"Zhou","year":"2009","journal-title":"J. Chem. Inf. Model."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1783","DOI":"10.1039\/c3cc37596j","article-title":"Metal-bound halogen atoms in crystal engineering","volume":"49","author":"Metrangolo","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1002\/open.201900337","article-title":"Halogen Bonding in Two-Dimensional Crystal Engineering","volume":"9","author":"Teyssandier","year":"2020","journal-title":"ChemistryOpen"},{"key":"ref_21","first-page":"143","article-title":"Halogen bonding in crystal engineering","volume":"Volume 262","author":"Ding","year":"2012","journal-title":"Recent Advances in Crystallography"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"900","DOI":"10.1055\/s-2008-1042935","article-title":"Organocatalysis through halogen-bond activation","volume":"2008","author":"Bruckmann","year":"2008","journal-title":"Synlett"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7028","DOI":"10.1002\/anie.201301351","article-title":"Organocatalysis by neutral multidentate halogen-bond donors","volume":"52","author":"Kniep","year":"2013","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/j.chemphys.2005.01.018","article-title":"Potential energy surfaces of CF4, CCl4 and CBr4 dimers","volume":"313","author":"Mahlanen","year":"2005","journal-title":"Chem. Phys."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/S0166-1280(96)04533-2","article-title":"Density functional study of the H3N\u25a1Cl2 system\u2014The importance of Hartree-Fock exchange in density functional methods","volume":"371","author":"Latajka","year":"1996","journal-title":"J. Mol. Struc. THEOCHEM"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2879","DOI":"10.1021\/jp962938d","article-title":"Systematic Theoretical Study of Structures and Bondings of the Charge-Transfer Complexes of Ammonia with HX, XY, and X2 (X and Y are Halogens)","volume":"101","author":"Zhang","year":"1997","journal-title":"J. Phys. Chem. A"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"9278","DOI":"10.1021\/jp982251o","article-title":"Charge-transfer complexes between dihalogen compounds and electron donors","volume":"102","author":"Alkorta","year":"1998","journal-title":"J. Phys. Chem. A"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4910","DOI":"10.1021\/ja00090a041","article-title":"The Nature of -Cl.cntdot..cntdot..cntdot.Cl- Intermolecular Interactions","volume":"116","author":"Price","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3838","DOI":"10.1002\/anie.200805739","article-title":"The nature of halogen...halogen interactions: A model derived from experimental charge-density analysis","volume":"48","author":"Bui","year":"2009","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1038\/nchem.112","article-title":"Halogen bonds as orthogonal molecular interactions to hydrogen bonds","volume":"1","author":"Voth","year":"2009","journal-title":"Nat. Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2264","DOI":"10.1021\/ic50092a011","article-title":"Crystal structure of the 1:1 molecular addition compound xenon difluoride-iodine pentafluoride, XeF2.IF5","volume":"9","author":"Jones","year":"2002","journal-title":"Inorg. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"522","DOI":"10.1021\/ic50038a006","article-title":"The Crystal and Molecular Structure of the Iodine Complex of 1-Oxa-4-selenacyclohexane, C4H8OSe.I2","volume":"5","author":"Maddox","year":"2002","journal-title":"Inorg. Chem."},{"key":"ref_33","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. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1007\/s00214-018-2388-8","article-title":"Polarization plays the key role in halogen bonding: A point-of-charge-based quantum mechanical study","volume":"138","author":"Ibrahim","year":"2019","journal-title":"Theor. Chem. Acc."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Varadwaj, A., Marques, H.M., and Varadwaj, P.R. (2019). Is the fluorine in molecules dispersive? Is molecular electrostatic potential a valid property to explore fluorine-centered non-covalent interactions?. Molecules, 24.","DOI":"10.3390\/molecules24030379"},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Varadwaj, P.R., Varadwaj, A., and Marques, H.M. (2019). Halogen bonding: A halogen-centered noncovalent interaction yet to be understood. Inorganics, 7.","DOI":"10.3390\/inorganics7030040"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2689","DOI":"10.1021\/acs.jpclett.6b00981","article-title":"Like charges attract?","volume":"7","author":"Zhao","year":"2016","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1002\/jcc.25125","article-title":"Do surfaces of positive electrostatic potential on different halogen derivatives in molecules attract? like attracting like!","volume":"39","author":"Varadwaj","year":"2018","journal-title":"J. Comput. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1836","DOI":"10.1002\/jcc.25836","article-title":"Nature of halogen-centered intermolecular interactions in crystal growth and design: Fluorine-centered interactions in dimers in crystalline hexafluoropropylene as a prototype","volume":"40","author":"Varadwaj","year":"2019","journal-title":"J. Comput. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1486","DOI":"10.1002\/cphc.201800023","article-title":"Revealing factors influencing the fluorine-centered non-covalent interactions in some fluorine-substituted molecular complexes: Insights from first-principles studies","volume":"19","author":"Varadwaj","year":"2018","journal-title":"ChemPhysChem"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"7180","DOI":"10.1021\/acs.cgd.0c00791","article-title":"Understanding the interplay of dispersion, charge transfer, and electrostatics in noncovalent interactions: The case of bromine\u2013carbonyl short contacts","volume":"20","author":"Alvarez","year":"2020","journal-title":"Cryst. Growth Des."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1107\/S205225251303491X","article-title":"Type II halogen...halogen contacts are halogen bonds","volume":"1","author":"Metrangolo","year":"2014","journal-title":"IUCrJ"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"21824","DOI":"10.1021\/acsomega.0c02887","article-title":"Unconventional type III halogen...halogen interactions: A quantum mechanical elucidation of sigma-hole...sigma-hole and di-sigma-hole interactions","volume":"5","author":"Ibrahim","year":"2020","journal-title":"ACS Omega"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"8725","DOI":"10.1021\/ja00205a027","article-title":"The nature of halogen...halogen interactions: Are short halogen contacts due to specific attractive forces or due to close packing of nonspherical atoms?","volume":"111","author":"Desiraju","year":"1989","journal-title":"J. Am. Chem. Soc."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"3386","DOI":"10.1039\/D1CP02706A","article-title":"Unusual Chalcogen\u2219\u2219\u2219Chalcogen Interactions in Like\u2219\u2219\u2219Like and Unlike Y=C=Y\u2219\u2219\u2219Y=C=Y Complexes (Y = O, S, and Se)","volume":"24","author":"Ibrahim","year":"2022","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1002\/wcms.19","article-title":"The electrostatic potential: An overview","volume":"1","author":"Murray","year":"2011","journal-title":"Wiley Interdiscip. Rev. Comput. Mol. Sci."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"3754","DOI":"10.1073\/pnas.79.12.3754","article-title":"Electrostatic potential molecular surfaces","volume":"79","author":"Weiner","year":"1982","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"108097","DOI":"10.1016\/j.jmgm.2021.108097","article-title":"R(*)-hole interactions of group IV-VII radical-containing molecules: A comparative study","volume":"111","author":"Ibrahim","year":"2022","journal-title":"J. Mol. Graph. Model."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"13223","DOI":"10.1002\/slct.202003231","article-title":"\u00b1\u03c0-Hole Interactions: A Comparative Investigation Based on Boron-Containing Molecules","volume":"5","author":"Ibrahim","year":"2020","journal-title":"ChemistrySelect"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1007\/s11224-021-01817-8","article-title":"\u03c0-Hole interactions of group III\u2013VI elements with \u03c0-systems and Lewis bases: A comparative study","volume":"33","author":"Ibrahim","year":"2022","journal-title":"Struct. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"11856","DOI":"10.1002\/slct.202103092","article-title":"\u03c3-Hole interactions of tetrahedral group iv\u2013viii lewis acid centers with lewis bases: A comparative study","volume":"6","author":"Ibrahim","year":"2021","journal-title":"ChemistrySelect"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"21631","DOI":"10.1021\/acsomega.0c02362","article-title":"Sigma-hole and lone-pair hole interactions in chalcogen-containing complexes: A comparative study","volume":"5","author":"Ibrahim","year":"2020","journal-title":"ACS Omega"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"4011","DOI":"10.1039\/D0RA09564H","article-title":"Comparison of \u00b1\u03c3-hole and \u00b1R-hole interactions formed by tetrel-containing complexes: A computational study","volume":"11","author":"Ibrahim","year":"2021","journal-title":"RSC Adv."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3569","DOI":"10.1007\/s11696-020-01187-1","article-title":"Comparative investigation of \u00b1\u03c3\u2013hole interactions of carbon-containing molecules with Lewis bases, acids and di-halogens","volume":"74","author":"Ibrahim","year":"2020","journal-title":"Chem. Pap."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"5489","DOI":"10.1002\/slct.201900603","article-title":"A computational investigation of unconventional lone-pair hole interactions of group V\u2013VIII elements","volume":"4","author":"Ibrahim","year":"2019","journal-title":"ChemistrySelect"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"4022","DOI":"10.1039\/D0RA09765A","article-title":"External electric field effects on the \u03c3-hole and lone-pair hole interactions of group V elements: A comparative investigation","volume":"11","author":"Ibrahim","year":"2021","journal-title":"RSC Adv."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"8952","DOI":"10.1002\/chem.200600523","article-title":"The nature of halogen...halogen synthons: Crystallographic and theoretical studies","volume":"12","author":"Awwadi","year":"2006","journal-title":"Chemistry"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"19330","DOI":"10.1021\/acsomega.1c03183","article-title":"On the potentiality of X-T-X3 compounds (T = C, Si, and Ge, and X = F, Cl, and Br) as tetrel- and halogen-bond donors","volume":"6","author":"Ibrahim","year":"2021","journal-title":"ACS Omega"},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/j.comptc.2014.10.005","article-title":"Evaluating common QTAIM and NCI interpretations of the electron density concentration through IQA interaction energies and 1D cross-sections of the electron and deformation density distributions","volume":"1053","author":"Cukrowski","year":"2015","journal-title":"Comput. Theor. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"6498","DOI":"10.1021\/ja100936w","article-title":"Revealing noncovalent interactions","volume":"132","author":"Johnson","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"184111","DOI":"10.1063\/1.3426316","article-title":"Density fitting and Cholesky decomposition approximations in symmetry-adapted perturbation theory: Implementation and application to probe the nature of pi-pi interactions in linear acenes","volume":"132","author":"Hohenstein","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1002\/wcms.93","article-title":"PSI4: An open-source ab initio electronic structure program","volume":"2","author":"Turney","year":"2012","journal-title":"Wiley Interdiscip. Rev. Comput. Mol. Sci."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1103\/PhysRev.46.618","article-title":"Note on an approximation treatment for many-electron systems","volume":"46","author":"Plesset","year":"1934","journal-title":"Phys. Rev."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1007","DOI":"10.1063\/1.456153","article-title":"Gaussian basis sets for use in correlated molecular calculations. I. The atoms boron through neon and hydrogen","volume":"90","author":"Dunning","year":"1989","journal-title":"J. Chem. Phys."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1358","DOI":"10.1063\/1.464303","article-title":"Gaussian basis sets for use in correlated molecular calculations. III. The atoms aluminum through argon","volume":"98","author":"Woon","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"32811","DOI":"10.1039\/C9RA08007D","article-title":"Comparative investigation of interactions of hydrogen, halogen and tetrel bond donors with electron-rich and electron-deficient \u03c0-systems","volume":"9","author":"Ibrahim","year":"2019","journal-title":"RSC Adv."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"3319","DOI":"10.1021\/acsomega.0c05795","article-title":"Cospatial sigma-hole and lone pair interactions of square-pyramidal pentavalent halogen compounds with pi-systems: A quantum mechanical study","volume":"6","author":"Ibrahim","year":"2021","journal-title":"ACS Omega"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1007\/s00214-018-2207-2","article-title":"Role and nature of halogen bonding in inhibitor \u2026 receptor complexes for drug discovery: Casein kinase-2 (CK2) inhibition as a case study","volume":"137","author":"Ibrahim","year":"2018","journal-title":"Theor. Chem. Acc."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1007\/s00894-018-3752-2","article-title":"Quantum-mechanical investigation of tetrel bond characteristics based on the point-of-charge (PoC) approach","volume":"24","author":"Ibrahim","year":"2018","journal-title":"J. Mol. Model."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"444","DOI":"10.1080\/10426507.2018.1528255","article-title":"A new insight for chalcogen bonding based on Point-of-Charge approach","volume":"194","author":"Ibrahim","year":"2019","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1080\/00268977000101561","article-title":"The calculation of small molecular interactions by the differences of separate total energies. Some procedures with reduced errors","volume":"19","author":"Boys","year":"1970","journal-title":"Mol. Phys."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"9","DOI":"10.1021\/ar00109a003","article-title":"Atoms in molecules","volume":"18","author":"Bader","year":"1985","journal-title":"Acc. Chem. Res."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","article-title":"VMD: Visual molecular dynamics","volume":"14","author":"Humphrey","year":"1996","journal-title":"J. Mol. Graph."},{"key":"ref_75","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G.A. (Gaussian 09, 2009). Gaussian 09, Revision E01."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"094106","DOI":"10.1063\/1.4867135","article-title":"Levels of symmetry adapted perturbation theory (SAPT). I. Efficiency and performance for interaction energies","volume":"140","author":"Parker","year":"2014","journal-title":"J. Chem. Phys."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/6\/3114\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T22:36:11Z","timestamp":1760135771000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/23\/6\/3114"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,3,14]]},"references-count":76,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2022,3]]}},"alternative-id":["ijms23063114"],"URL":"https:\/\/doi.org\/10.3390\/ijms23063114","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,3,14]]}}}