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Initiation Project of Guizhou Medical University","award":["J[2023]007"],"award-info":[{"award-number":["J[2023]007"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>In recent years, the non-covalent interactions between chalcogen centers have aroused substantial research interest because of their potential applications in organocatalysis, materials science, drug design, biological systems, crystal engineering, and molecular recognition. However, studies on \u03c0-hole-type chalcogen\u2219\u2219\u2219chalcogen interactions are scarcely reported in the literature. Herein, the \u03c0-hole-type intermolecular chalcogen\u2219\u2219\u2219chalcogen interactions in the model complexes formed between XO2 (X = S, Se, Te) and CH3YCH3 (Y = O, S, Se, Te) were systematically studied by using quantum chemical computations. The model complexes are stabilized via one primary X\u2219\u2219\u2219Y chalcogen bond (ChB) and the secondary C\u2212H\u2219\u2219\u2219O hydrogen bonds. The binding energies of the studied complexes are in the range of \u221221.6~\u221260.4 kJ\/mol. The X\u2219\u2219\u2219Y distances are significantly smaller than the sum of the van der Waals radii of the corresponding two atoms. The X\u2219\u2219\u2219Y ChBs in all the studied complexes except for the SO2\u2219\u2219\u2219CH3OCH3 complex are strong in strength and display a partial covalent character revealed by conducting the quantum theory of atoms in molecules (QTAIM), a non-covalent interaction plot (NCIplot), and natural bond orbital (NBO) analyses. The symmetry-adapted perturbation theory (SAPT) analysis discloses that the X\u2219\u2219\u2219Y ChBs are primarily dominated by the electrostatic component.<\/jats:p>","DOI":"10.3390\/ijms242216193","type":"journal-article","created":{"date-parts":[[2023,11,13]],"date-time":"2023-11-13T02:02:42Z","timestamp":1699840962000},"page":"16193","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["Computational Insight into the Nature and Strength of the \u03c0-Hole Type Chalcogen\u2219\u2219\u2219Chalcogen Interactions in the XO2\u2219\u2219\u2219CH3YCH3 Complexes (X = S, Se, Te; Y = O, S, Se, Te)"],"prefix":"10.3390","volume":"24","author":[{"given":"Fengying","family":"Lei","sequence":"first","affiliation":[{"name":"School of Basic Medical Sciences\/School of Biology and Engineering, Guizhou Medical University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qingyu","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Basic Medical Sciences\/School of Biology and Engineering, Guizhou Medical University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yeshuang","family":"Zhong","sequence":"additional","affiliation":[{"name":"School of Basic Medical Sciences\/School of Biology and Engineering, Guizhou Medical University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinai","family":"Cui","sequence":"additional","affiliation":[{"name":"School of Basic Medical Sciences\/School of Biology and Engineering, Guizhou Medical University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jie","family":"Yu","sequence":"additional","affiliation":[{"name":"School of Basic Medical Sciences\/School of Biology and Engineering, Guizhou Medical University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4978-4363","authenticated-orcid":false,"given":"Zuquan","family":"Hu","sequence":"additional","affiliation":[{"name":"School of Basic Medical Sciences\/School of Biology and Engineering, Guizhou Medical University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8631-7671","authenticated-orcid":false,"given":"Gang","family":"Feng","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Chongqing University, Daxuecheng South Rd. 55, Chongqing 401331, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0842-9402","authenticated-orcid":false,"given":"Zhu","family":"Zeng","sequence":"additional","affiliation":[{"name":"School of Basic Medical Sciences\/School of Biology and Engineering, Guizhou Medical University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tao","family":"Lu","sequence":"additional","affiliation":[{"name":"School of Basic Medical Sciences\/School of Biology and Engineering, Guizhou Medical University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,11,10]]},"reference":[{"key":"ref_1","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_2","doi-asserted-by":"crossref","first-page":"1889","DOI":"10.1515\/pac-2018-0713","article-title":"Definition of the chalcogen bond (IUPAC Recommendations 2019)","volume":"91","author":"Aakeroy","year":"2019","journal-title":"Pure Appl. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1880","DOI":"10.1002\/anie.201809432","article-title":"Chalcogen Bonding: An Overview","volume":"58","author":"Vogel","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1313","DOI":"10.1021\/acs.accounts.9b00037","article-title":"The Chalcogen Bond in Crystalline Solids: A World Parallel to Halogen Bond","volume":"52","author":"Scilabra","year":"2019","journal-title":"Acc. Chem. Res."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1007\/s00894-011-1089-1","article-title":"\u03c3-Holes, \u03c0-holes and electrostatically-driven interactions","volume":"18","author":"Murray","year":"2012","journal-title":"J. Mol. Model."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2496","DOI":"10.1002\/cphc.201500314","article-title":"The bright future of unconventional \u03c3\/\u03c0-hole interactions","volume":"16","author":"Mooibroek","year":"2015","journal-title":"ChemPhysChem"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"5072","DOI":"10.1021\/acs.chemrev.5b00527","article-title":"\u03c3-Hole bond vs \u03c0-hole bond: A comparison based on halogen bond","volume":"116","author":"Wang","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"32166","DOI":"10.1039\/C7CP06793C","article-title":"The \u03c3-hole revisited","volume":"19","author":"Politzer","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Politzer, P., and Murray, J.S. (2019). An Overview of Strengths and Directionalities of Noncovalent Interactions: \u03c3-Holes and \u03c0-Holes. Crystals, 9.","DOI":"10.3390\/cryst9030165"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"11178","DOI":"10.1039\/c3cp00054k","article-title":"Halogen bonding and other \u03c3-hole interactions: A perspective","volume":"15","author":"Politzer","year":"2013","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Politzer, P., and Murray, J.S. (2017). \u03c3-Hole Interactions: Perspectives and Misconceptions. Crystals, 7.","DOI":"10.3390\/cryst7070212"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Frontera, A. (2020). \u03c3- and \u03c0-Hole Interactions. Crystals, 10.","DOI":"10.3390\/cryst10090721"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6514","DOI":"10.1021\/acs.jpca.1c05431","article-title":"Dissection of the Origin of \u03c0-Holes and the Noncovalent Bonds in Which They Engage","volume":"125","author":"Scheiner","year":"2021","journal-title":"J. Phys. Chem. A"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"6849","DOI":"10.1021\/jp403200j","article-title":"Origin of attraction in chalcogen\u2013nitrogen interaction of 1,2,5-chalcogenadiazole dimers","volume":"117","author":"Tsuzuki","year":"2013","journal-title":"J. Phys. Chem. B"},{"key":"ref_15","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_16","doi-asserted-by":"crossref","first-page":"2478","DOI":"10.1021\/acs.chemrev.5b00484","article-title":"The halogen bond","volume":"116","author":"Cavallo","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Gilli, G., and Gilli, P. (2009). The Nature of the Hydrogen Bond, Oxford University Press.","DOI":"10.1093\/acprof:oso\/9780199558964.001.0001"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3183","DOI":"10.1021\/jp501449v","article-title":"Effects of charge and substituent on the S\u00b7\u00b7\u00b7N chalcogen bond","volume":"118","author":"Adhikari","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"10849","DOI":"10.1021\/jp509212t","article-title":"Chalcogen Bonding between Tetravalent SF4 and Amines","volume":"118","author":"Nziko","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"17384","DOI":"10.1002\/chem.201704406","article-title":"Exploiting the \u03c3-hole concept: An Infrared and Raman-based characterization of the S\u00b7\u00b7\u00b7O chalcogen bond between 2,2,4,4-tetrafluoro-1,3-dithiethane and dimethyl ether","volume":"23","author":"Geboes","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"20829","DOI":"10.1039\/C9CP04006D","article-title":"Chalcogen bonding of two ligands to hypervalent YF4 (Y = S, Se, Te, Po)","volume":"21","author":"Zierkiewicz","year":"2019","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"24659","DOI":"10.1039\/C9CP04628C","article-title":"Rotational characterization of S\u00b7\u00b7\u00b7F chalcogen bonds in the complex of 2,2,4,4-tetrafluoro-1,3-dithietane and difluoromethane","volume":"21","author":"Lu","year":"2019","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"688","DOI":"10.1002\/jcc.26489","article-title":"Chalcogen bonds: Hierarchical ab initio benchmark and density functional theory performance study","volume":"42","author":"Santos","year":"2021","journal-title":"J. Comput. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2078","DOI":"10.1080\/00268976.2014.884730","article-title":"Cooperative interaction between \u03c0-hole and single-electron \u03c3-hole interactions in O2S\u00b7\u00b7\u00b7NCX\u00b7\u00b7\u00b7CH3 and O2Se\u00b7\u00b7\u00b7NCX\u00b7\u00b7\u00b7CH3 complexes (X = F, Cl, Br and I)","volume":"112","author":"Esrafili","year":"2014","journal-title":"Mol. Phys."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1002\/qua.25076","article-title":"Homonuclear chalcogen\u2013chalcogen bond interactions in complexes pairing YO3 and YHX molecules (Y = S, Se; X = H, Cl, Br, CCH, NC, OH, OCH3): Influence of substitution and cooperativity","volume":"116","author":"Esrafili","year":"2016","journal-title":"Int. J. Quantum Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"15822","DOI":"10.1002\/anie.201810637","article-title":"Unveiling the Sulfur\u2013Sulfur Bridge: Accurate Structural and Energetic Characterization of a Homochalcogen Intermolecular Bond","volume":"57","author":"Obenchain","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"9175","DOI":"10.1021\/jacs.9b03806","article-title":"Chalcogen\u2013Chalcogen Bonding Catalysis Enables Assembly of Discrete Molecules","volume":"141","author":"Wang","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3117","DOI":"10.1021\/jacs.9b12610","article-title":"Dual chalcogen\u2013chalcogen bonding catalysis","volume":"142","author":"Wang","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"ref_29","doi-asserted-by":"crossref","unstructured":"Pale, P., and Mamane, V. (2023). Chalcogen Bonding Catalysis: Tellurium, the Last Frontier?. Chem. Eur. J., 29.","DOI":"10.1002\/chem.202302755"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"6347","DOI":"10.1038\/s41467-023-42129-1","article-title":"Supramolecular catalysis with ethers enabled by dual chalcogen bonding activation","volume":"14","author":"Zhao","year":"2023","journal-title":"Nat. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"213464","DOI":"10.1016\/j.ccr.2020.213464","article-title":"Chalcogen bonding in materials chemistry","volume":"422","author":"Ho","year":"2020","journal-title":"Coordin. Chem. Rev."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"4383","DOI":"10.1021\/jm501853m","article-title":"A Survey of the Role of Noncovalent Sulfur Interactions in Drug Design","volume":"58","author":"Beno","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1622","DOI":"10.1021\/acschembio.1c00441","article-title":"Chalcogen Bonds Involving Selenium in Protein Structures","volume":"16","author":"Carugo","year":"2021","journal-title":"ACS Chem. Biol."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1701","DOI":"10.1021\/acschembio.1c00417","article-title":"Charge Assisted S\/Se Chalcogen Bonds in SAM Riboswitches: A Combined PDB and ab Initio Study","volume":"16","author":"Frontera","year":"2021","journal-title":"ACS Chem. Biol."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"17656","DOI":"10.1039\/D1CP01929E","article-title":"Selenium chalcogen bonds are involved in protein\u2013carbohydrate recognition: A combined PDB and theoretical study","volume":"23","author":"Riveras","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Biswal, H.S., Sahu, A.K., Galm\u00e9s, B., Frontera, A., and Chopra, D. (2022). Se\u00b7\u00b7\u00b7O\/S and S\u00b7\u00b7\u00b7O chalcogen bonds in small molecules and proteins: A combined CSD and PDB study. ChemBioChem, 23.","DOI":"10.1002\/cbic.202100498"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2010","DOI":"10.1021\/acs.chemrev.7b00449","article-title":"From Noncovalent Chalcogen\u2013Chalcogen Interactions to Supramolecular Aggregates: Experiments and Calculations","volume":"118","author":"Gleiter","year":"2018","journal-title":"Chem. Rev."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"213084","DOI":"10.1016\/j.ccr.2019.213084","article-title":"Chalcogen bonding in crystalline diselenides and selenocyanates: From molecules of pharmaceutical interest to conducting materials","volume":"403","author":"Dhaka","year":"2020","journal-title":"Coordin. Chem. Rev."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"214556","DOI":"10.1016\/j.ccr.2022.214556","article-title":"Chalcogen bonding in coordination chemistry","volume":"464","author":"Mahmudov","year":"2022","journal-title":"Coordin. Chem. Rev."},{"key":"ref_40","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_41","doi-asserted-by":"crossref","first-page":"213243","DOI":"10.1016\/j.ccr.2020.213243","article-title":"Chalcogen-bond driven molecular recognition at work","volume":"413","author":"Biot","year":"2020","journal-title":"Coordin. Chem. Rev."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"2666","DOI":"10.1021\/ja056827g","article-title":"Theoretical Investigations on Chalcogen\u2212Chalcogen Interactions: What Makes These Nonbonded Interactions Bonding?","volume":"128","author":"Bleiholder","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"2249","DOI":"10.1021\/ic062110y","article-title":"Theoretical Investigations on Heteronuclear Chalcogen\u2014Chalcogen Interactions: On the Nature of Weak Bonds between Chalcogen Centers","volume":"46","author":"Bleiholder","year":"2007","journal-title":"Inorg. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2540","DOI":"10.1002\/cphc.201800409","article-title":"Chalcogen Bonding in Protein\u2212Ligand Complexes: PDB Survey and Quantum Mechanical Calculations","volume":"19","year":"2018","journal-title":"Chemphyschem"},{"key":"ref_45","first-page":"57","article-title":"Chalcogen Bonds in Small-Organic Molecule Compounds Derived from the Cambridge Structural Database (CSD)","volume":"10","author":"Lundemba","year":"2021","journal-title":"Cryst. Struct. Theory Appl."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1080\/07391102.2022.2143427","article-title":"Chalcogen bonds formed by protein sulfur atoms in proteins. A survey of high-resolution structures deposited in the protein data bank","volume":"91","author":"Carugo","year":"2022","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Pi\u00f1a, M.d.L.N., and Bauz\u00e1, A. (2023). On the Importance of Halogen and Chalcogen Bonds in the Solid State of Nucleic Acids: A Combined Crystallographic and Theoretical Perspective. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms241713035"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1683","DOI":"10.1246\/bcsj.20150224","article-title":"Chalcogen\u2013chalcogen interactions in furan-YHX and thiophene-YHX complexes (X = F, Cl, Br; Y = S, Se): An ab initio study","volume":"88","author":"Esrafili","year":"2015","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1007\/s00894-018-3895-1","article-title":"The chalcogen bond in F2P(S)N\u00b7\u00b7\u00b7SX2, F2PNS\u00b7\u00b7\u00b7SX2, F2PSN\u00b7\u00b7\u00b7SX2 (X = F, Cl, Br, OH, CH3, NH2) complexes","volume":"25","author":"Yan","year":"2019","journal-title":"J. Mol. Model."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"7221","DOI":"10.1039\/D3SC00849E","article-title":"Evidence for and evaluation of fluorine\u2013tellurium chalcogen bonding","volume":"14","author":"Weiss","year":"2023","journal-title":"Chem. Sci."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"12791","DOI":"10.1039\/D1DT02704B","article-title":"Recent advances in sulfur tetrafluoride chemistry: Syntheses, structures, and applications","volume":"50","author":"Matsumoto","year":"2021","journal-title":"Dalton Trans."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"975","DOI":"10.1039\/D1CE01364E","article-title":"Square tetravalent chalcogen bonds in dimeric aggregates: A joint crystallographic survey and theoretical study","volume":"24","author":"Liang","year":"2022","journal-title":"CrystEngComm"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"11313","DOI":"10.1039\/C9CP01033E","article-title":"Unexpected chalcogen bonds in tetravalent sulfur compounds","volume":"21","author":"Franconetti","year":"2019","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"32828","DOI":"10.1021\/acsomega.3c03981","article-title":"Sigma-Hole and Lone-Pair-Hole Site-Based Interactions of Seesaw Tetravalent Chalcogen-Bearing Molecules with Lewis Bases","volume":"8","author":"Ibrahim","year":"2023","journal-title":"ACS Omega"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"3835","DOI":"10.1021\/jp501932g","article-title":"Substituent effects in the noncovalent bonding of SO2 to molecules containing a carbonyl group. The dominating role of the chalcogen bond","volume":"118","author":"Azofra","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"10799","DOI":"10.1039\/D1CP00997D","article-title":"Interaction topologies of the S\u00b7\u00b7\u00b7O chalcogen bond: The conformational equilibrium of the cyclohexanol\u00b7\u00b7\u00b7SO2 cluster","volume":"23","author":"Jin","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"17185","DOI":"10.1039\/D2CP01852G","article-title":"Hydrogen bonding with polonium","volume":"24","author":"Tulsiyan","year":"2022","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"e202300124","DOI":"10.1002\/cphc.202300124","article-title":"An experimental exploration of C\u2212H\u00b7\u00b7\u00b7X hydrogen bond in [CHCl3\u2212X(CH3)2] complexes (X= O, S, and Se)","volume":"24","author":"Pal","year":"2023","journal-title":"ChemPhysChem"},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"Beckmann, J.L., Krieft, J., Vishnevskiy, Y.V., Neumann, B., Stammler, H.-G., and Mitzel, N.W. (2023). A bidentate antimony pnictogen bonding host-system. Angew. Chem. Int. Ed., 62.","DOI":"10.1002\/anie.202310439"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"659","DOI":"10.1007\/s00894-008-0280-5","article-title":"\u03c3-hole bonding between like atoms; a fallacy of atomic charges","volume":"14","author":"Politzer","year":"2008","journal-title":"J. Mol. Model."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"893","DOI":"10.1021\/cr00005a013","article-title":"A quantum theory of molecular structure and its applications","volume":"91","author":"Bader","year":"1991","journal-title":"Chem. Rev."},{"key":"ref_62","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_63","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/wcms.51","article-title":"Natural bond orbital methods","volume":"2","author":"Glendening","year":"2011","journal-title":"WIREs Comput. Mol. Sci."},{"key":"ref_64","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."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"5806","DOI":"10.1021\/jp8111556","article-title":"Consistent van der Waals Radii for the Whole Main Group","volume":"113","author":"Mantina","year":"2009","journal-title":"J. Phys. Chem. A"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"2832","DOI":"10.1039\/b801115j","article-title":"Covalent radii revisited","volume":"21","author":"Cordero","year":"2008","journal-title":"Dalton Trans."},{"key":"ref_67","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. B"},{"key":"ref_68","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_69","doi-asserted-by":"crossref","first-page":"11113","DOI":"10.1063\/1.1622924","article-title":"Systematically convergent basis sets with relativistic pseudopotentials. II. Small-core pseudopotentials and correlation consistent basis sets for the post-d group 16\u201318 elements","volume":"119","author":"Peterson","year":"2003","journal-title":"J. Chem. Phys."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"4814","DOI":"10.1021\/acs.jcim.9b00725","article-title":"New Basis Set Exchange: An Open, Up-to-Date Resource for the Molecular Sciences Community","volume":"59","author":"Pritchard","year":"2019","journal-title":"J. Chem. Inf. Model."},{"key":"ref_71","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_72","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2016). Gaussian 16, Revision A.03, Gaussian, Inc."},{"key":"ref_73","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_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","doi-asserted-by":"crossref","first-page":"3185","DOI":"10.1021\/acs.jctc.7b00174","article-title":"Psi4 1.1: An open-source electronic structure program emphasizing automation, advanced libraries, and interoperability","volume":"13","author":"Parrish","year":"2017","journal-title":"J. Chem. Theory Comput."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/22\/16193\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T21:21:24Z","timestamp":1760131284000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/22\/16193"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,11,10]]},"references-count":75,"journal-issue":{"issue":"22","published-online":{"date-parts":[[2023,11]]}},"alternative-id":["ijms242216193"],"URL":"https:\/\/doi.org\/10.3390\/ijms242216193","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,11,10]]}}}