{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T02:05:53Z","timestamp":1760148353085,"version":"build-2065373602"},"reference-count":98,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2023,4,26]],"date-time":"2023-04-26T00:00:00Z","timestamp":1682467200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Polish Ministry of Science and Higher Education","award":["8211104160\/K14W03D10"],"award-info":[{"award-number":["8211104160\/K14W03D10"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The set of TX3-TrX2 (T = C, Si, Ge; Tr = B, Al, Ga; X = F, Cl, Br) molecules offers a rather unique opportunity to study both \u03c3-hole and \u03c0-hole dimerization on the tetrel and triel ends, respectively. According to the molecular electrostatic potential (MEP) distribution, the \u03c0-hole extrema (acidic sites) were more intense than their \u03c3-hole counterparts. The molecules owning the most (CX3-AlX2) and least (SiX3-BX2) intense \u03c0-holes were chosen to evaluate their capacities to attract one and two HCN molecules (Lewis bases). We discovered that the energetic characteristics of \u03c0-hole dimers severely conflict with the monomers MEP pattern since the weakest \u03c0-hole monomer forms a dimer characterized by interaction energy compared to those created by the monomers with noticeably greater power in the \u03c0-hole region. This outcome is due to the deformation of the weakest \u03c0-hole donor. Furthermore, the MEP analysis for monomers in the geometry of respective dimers revealed a \u201cresidual \u03c0-hole\u201d site that was able to drive second ligand attachment, giving rise to the two \u201cunusual trimers\u201d examined further by the NCI and QTAIM analyses. Apart from them, the \u03c0-hole\/\u03c0-hole and \u03c3-hole\/\u03c0-hole trimers have also been obtained throughout this study and described using energetic and geometric parameters. The SAPT approach revealed details of the bonding in one of the \u201cunusual trimers\u201d. Finally, Born-Oppenheimer Molecular Dynamics (BOMD) simulations were carried out to investigate the time evolution of the interatomic distances of the studied complexes as well as their stability.<\/jats:p>","DOI":"10.3390\/ijms24097881","type":"journal-article","created":{"date-parts":[[2023,4,27]],"date-time":"2023-04-27T02:50:00Z","timestamp":1682563800000},"page":"7881","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Static and Dynamical Quantum Studies of CX3-AlX2 and CSiX3-BX2 (X = F, Cl, Br) Complexes with Hydrocyanic Acid: Unusual Behavior of Strong \u03c0-Hole at Triel Center"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6495-6963","authenticated-orcid":false,"given":"Mariusz","family":"Michalczyk","sequence":"first","affiliation":[{"name":"Faculty of Chemistry, Wroc\u0142aw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9712-6862","authenticated-orcid":false,"given":"Kamil","family":"Wojtkowiak","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, ul. F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2952-9739","authenticated-orcid":false,"given":"Jaros\u0142aw J.","family":"Panek","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, ul. F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6601-9124","authenticated-orcid":false,"given":"Aneta","family":"Jezierska","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, University of Wroc\u0142aw, ul. F. Joliot-Curie 14, 50-383 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4038-5959","authenticated-orcid":false,"given":"Wiktor","family":"Zierkiewicz","sequence":"additional","affiliation":[{"name":"Faculty of Chemistry, Wroc\u0142aw University of Science and Technology, Wybrze\u017ce Wyspia\u0144skiego 27, 50-370 Wroc\u0142aw, Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2023,4,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1002\/qua.560440709","article-title":"Surface electrostatic potentials of halogenated methanes as indicators of directional intermolecular interactions","volume":"44","author":"Brinck","year":"1992","journal-title":"Int. J. Quantum Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3104","DOI":"10.1021\/ja973109o","article-title":"Intramolecular Nonbonded S\u2026O Interaction Recognized in (Acylimino) thiadiazoline Derivatives as Angiotensin II Receptor Antagonists and Related Compounds","volume":"120","author":"Nagao","year":"1998","journal-title":"Am. Chem. Soc."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2311","DOI":"10.1002\/anie.199523111","article-title":"Supramolecular synthons in crystal engineering\u2014A new organic synthesis","volume":"34","author":"Desiraju","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2237","DOI":"10.1021\/ja00242a001","article-title":"Bonding between nonbonded sulfur and oxygen atoms in selected organic molecules (a quantum chemical study)","volume":"109","author":"Poirier","year":"1987","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0065-2792(08)60016-3","article-title":"Secondary bonding to nonmetallic elements","volume":"15","author":"Alcock","year":"1972","journal-title":"Adv. Inorg. Chem. Radiochem."},{"key":"ref_6","first-page":"90","article-title":"Action of the halogens on the methylamines","volume":"18","author":"Remsen","year":"1896","journal-title":"Am. Chem. J."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1039\/JS8631600239","article-title":"XXVIII.\u2014On the iodide of iodammonium","volume":"16","author":"Guthrie","year":"1863","journal-title":"Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","unstructured":"Malone, J.F., and McDonald, W.S. (1970). Crystal structures of triphenylgallium and triphenylindium. J. Chem. Soc. A, 3362\u20133367.","DOI":"10.1039\/j19700003362"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"818","DOI":"10.1002\/cphc.202100132","article-title":"Crystallographic and Theoretical Evidences of Anion\u22ef Anion Interaction","volume":"22","author":"Wysokinski","year":"2021","journal-title":"ChemPhysChem"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"130155","DOI":"10.1016\/j.molstruc.2021.130155","article-title":"An iron (II) complex of trans, trans, trans-bis (azido) bis (4-amino-3, 5-bis (2-pyridyl)-1, 2, 4-triazole): Insight into molecular and supramolecular structures using Hirshfeld surface analysis and DFT studies","volume":"1235","author":"Setifi","year":"2021","journal-title":"Mol. Struct."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"433","DOI":"10.1002\/cphc.202100056","article-title":"Molecular Recognition","volume":"22","author":"Mooibroek","year":"2021","journal-title":"ChemPhysChem"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"4686","DOI":"10.1039\/D0DT04337K","article-title":"Synthesis of Ni (ii)\u2013Mn (ii) complexes using a new mononuclear Ni (ii) complex of an unsymmetrical N2O3 donor ligand: Structures, magnetic properties and catalytic oxidase activity","volume":"50","author":"Maity","year":"2021","journal-title":"Dalton Trans."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"129188","DOI":"10.1016\/j.molstruc.2020.129188","article-title":"A supramolecular 3D structure constructed from a new metal chelate self-assembled from Sn(NCS)2 and phenyl(pyridin-2-yl)methylenepicolinohydrazide","volume":"1224","author":"Mahmoudi","year":"2021","journal-title":"J. Mol. Struct."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"642","DOI":"10.1021\/acs.cgd.0c01429","article-title":"Tetrel and pnictogen bonds complement hydrogen and halogen bonds in framing the interactional landscape of barbituric acids","volume":"21","author":"Kumar","year":"2021","journal-title":"Cryst. Growth Des."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3084","DOI":"10.1039\/D1CE00221J","article-title":"Spodium bonding in five coordinated Zn (II): A new player in crystal engineering?","volume":"23","author":"Gomila","year":"2021","journal-title":"CrystEngComm"},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Frontera, A., and Bauz\u00e1, A. (2021). On the Importance of \u03c3\u2013Hole Interactions in Crystal Structures. Crystals, 11.","DOI":"10.3390\/cryst11101205"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"14385","DOI":"10.1002\/anie.202104592","article-title":"Anion\u22efAnion Coinage Bonds: The Case of Tetrachloridoaurate","volume":"60","author":"Daolio","year":"2021","journal-title":"Angew. Chem. Int. Edit."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3276","DOI":"10.1039\/D1CE00256B","article-title":"Crystal engineering with pyrazolyl-thiazole derivatives: Structure-directing role of \u03c0-stacking and \u03c3-hole interactions","volume":"23","author":"Ahmed","year":"2021","journal-title":"CrystEngComm"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1007\/s11224-019-01377-y","article-title":"Noncovalent functionalization of graphene via \u03c0-hole\u00b7\u00b7\u00b7 \u03c0 and \u03c3-hole\u00b7\u00b7\u00b7 \u03c0 interactions","volume":"31","author":"Zhang","year":"2020","journal-title":"Struct. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"7084","DOI":"10.1039\/D0CC02831B","article-title":"Formation of self-assembled supramolecular polymers by anti-electrostatic anion\u2013anion and halogen bonding interactions","volume":"56","author":"Zapata","year":"2020","journal-title":"Chem. Commun."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"8171","DOI":"10.1039\/D0CE01356K","article-title":"Supramolecular assemblies involving salt bridges: DFT and X-ray evidence of bipolarity","volume":"22","author":"Tripathi","year":"2020","journal-title":"CrystEngComm"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"579","DOI":"10.1107\/S2053229620006166","article-title":"Chimeric supramolecular synthons in Ph2Te2 (I2) Se","volume":"76","author":"Torubaev","year":"2020","journal-title":"Acta Crystallogr. C"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1002\/cphc.202000955","article-title":"Weak \u03c3-Hole Triel Bond between C5H5Tr (Tr = B, Al, Ga) and Haloethyne: Substituent and Cooperativity Effects","volume":"22","author":"Yang","year":"2021","journal-title":"ChemPhysChem"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"4818","DOI":"10.1039\/D0CP06547A","article-title":"Anion\u2013anion and anion\u2013neutral triel bonds","volume":"23","author":"Wysokinski","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Grabowski, S.J. (2020). The nature of triel bonds, a case of B and Al centres bonded with electron rich sites. Molecules, 25.","DOI":"10.3390\/molecules25112703"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"e25867","DOI":"10.1002\/qua.25867","article-title":"Carbene triel bonds between TrR3 (Tr = B, Al) and N-heterocyclic carbenes","volume":"119","author":"Chi","year":"2019","journal-title":"Int. J. Quantum Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1177","DOI":"10.1002\/jcc.25178","article-title":"Hydride-Triel Bonds","volume":"39","author":"Jablonski","year":"2018","journal-title":"Comput. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1080\/00268976.2017.1393118","article-title":"The triel bond: A potential force for tuning anion\u2013\u03c0 interactions","volume":"116","author":"Esrafili","year":"2018","journal-title":"Mol. Phys."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5702","DOI":"10.1039\/D1CP00242B","article-title":"Origins and properties of the tetrel bond","volume":"23","author":"Scheiner","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"10126","DOI":"10.1002\/chem.202002613","article-title":"Engineering Crystals Using sp3-C Centred Tetrel Bonding Interactions","volume":"26","author":"Roeleveld","year":"2020","journal-title":"Chem. Eur. J."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"213265","DOI":"10.1016\/j.ccr.2020.213265","article-title":"C (sp3) atoms as tetrel bond donors: A crystallographic survey","volume":"413","author":"Daolio","year":"2020","journal-title":"Coord. Chem. Rev."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"e25910","DOI":"10.1002\/qua.25910","article-title":"Comparison of \u03c3-hole and \u03c0-hole tetrel bonds in complexes of borazine with TH 3 F and F 2 TO\/H 2 TO (T = C, Si, Ge)","volume":"119","author":"Zhang","year":"2019","journal-title":"Int. J. Quantum Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1141","DOI":"10.1007\/s11224-019-01358-1","article-title":"Pnicogen and tetrel bonds\u2014Tetrahedral Lewis acid centres","volume":"30","author":"Grabowski","year":"2019","journal-title":"Struct. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Scheiner, S. (2018). Tetrel Bonding as a Vehicle for Strong and Selective Anion Binding. Molecules, 23.","DOI":"10.3390\/molecules23051147"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2550","DOI":"10.1021\/acs.jpca.7b12357","article-title":"Steric crowding in tetrel bonds","volume":"122","author":"Scheiner","year":"2018","journal-title":"Phys. Chem. A"},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Mahmoudi, G., Abedi, M., Lawrence, S.E., Zangrando, E., Babashkina, M.G., Klein, A., Frontera, A., and Safin, D.A. (2020). Tetrel Bonding and Other Non-Covalent Interactions Assisted Supramolecular Aggregation in a New Pb(II) Complex of an Isonicotinohydrazide. Molecules, 25.","DOI":"10.3390\/molecules25184056"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5289","DOI":"10.1039\/D0SC01559H","article-title":"Observations of tetrel bonding between sp3-carbon and THF","volume":"11","author":"Heywood","year":"2020","journal-title":"Chem. Sci."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Frontera, A. (2020). Tetrel Bonding Interactions Involving Carbon at Work: Recent Advances in Crystal Engineering and Catalysis. C-J. Carbon Res., 6.","DOI":"10.3390\/c6040060"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2389","DOI":"10.1039\/D0CE00102C","article-title":"Supramolecular lead (II) architectures engineered by tetrel bonds","volume":"22","author":"Afkhami","year":"2020","journal-title":"CrystEngComm"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.comptc.2018.11.011","article-title":"Tetrel bonding on graphene","volume":"1147","author":"Zhang","year":"2019","journal-title":"Comput. Theor. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"136584","DOI":"10.1016\/j.cplett.2019.07.012","article-title":"The ability of a tetrel bond to transition a neutral amino acid into a zwitterion","volume":"731","author":"Hou","year":"2019","journal-title":"Chem. Phys. Lett."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"6007","DOI":"10.1002\/chem.201900447","article-title":"Theoretical and Crystallographic Study of Lead (IV) Tetrel Bonding Interactions","volume":"25","author":"Franconetti","year":"2019","journal-title":"Chem. Eur. J."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"11208","DOI":"10.1039\/C9DT01953G","article-title":"\u201cLike\u2013like\u201d tetrel bonding interactions between Sn centres: A combined ab initio and CSD study","volume":"48","author":"Franconetti","year":"2019","journal-title":"Dalton Trans."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/j.ccr.2019.01.003","article-title":"Tetrel bonding interactions at work: Impact on tin and lead coordination compounds","volume":"384","author":"Bauza","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Solel, E., and Kozuch, S. (2018). On the power of geometry over tetrel bonds. Molecules, 23.","DOI":"10.3390\/molecules23112742"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"5033","DOI":"10.1039\/C8CE00919H","article-title":"On the importance of Pb\u22ef X (X = O, N, S, Br) tetrel bonding interactions in a series of tetra-and hexa-coordinated Pb (II) compounds","volume":"20","author":"Seth","year":"2018","journal-title":"CrystEngComm"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1007\/s00894-017-3573-8","article-title":"Close contacts involving germanium and tin in crystal structures: Experimental evidence of tetrel bonds","volume":"24","author":"Scilabra","year":"2018","journal-title":"Mol. Model."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1033","DOI":"10.1007\/s00894-007-0225-4","article-title":"\u03c3-hole bonding: Molecules containing group VI atoms","volume":"13","author":"Murray","year":"2007","journal-title":"Mol. Model"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1007\/s00894-006-0130-2","article-title":"Halogen bonding: The \u03c3-hole: Proceedings of \u201cModeling interactions in biomolecules II\u201d, Prague, September 5th\u20139th, 2005","volume":"13","author":"Clark","year":"2007","journal-title":"Mol. Model"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"16458","DOI":"10.1039\/D1CP02602J","article-title":"The \u03c0-hole revisited","volume":"23","author":"Politzer","year":"2021","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_51","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_52","doi-asserted-by":"crossref","first-page":"2747","DOI":"10.1007\/s00894-012-1591-0","article-title":"ETS-NOCV description of \u03c3-hole bonding","volume":"19","author":"Dyduch","year":"2013","journal-title":"Mol. Model."},{"key":"ref_53","unstructured":"Politzer, P., and Murray, J.S. (2009). Abstracts of Papers of the American Chemical Society, American Chemical Society."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"723","DOI":"10.1007\/s00894-008-0386-9","article-title":"Expansion of the \u03c3-hole concept","volume":"15","author":"Murray","year":"2009","journal-title":"Mol. Model."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1007\/s00894-006-0154-7","article-title":"An overview of halogen bonding","volume":"13","author":"Politzer","year":"2007","journal-title":"J. Mol. Model."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2286","DOI":"10.1002\/qua.21352","article-title":"A predicted new type of directional noncovalent interaction","volume":"107","author":"Murray","year":"2007","journal-title":"Int. J. Quantum Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"138","DOI":"10.2174\/1570193X18666210225121327","article-title":"Polyhedra, Tiles and Graphene Defects: The Case of Tetraoctite","volume":"19","author":"Elguero","year":"2022","journal-title":"Mini-Rev. Org. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"113268","DOI":"10.1016\/j.comptc.2021.113268","article-title":"The influence of monomer deformation on triel and tetrel bonds between TrR3\/TR4 (Tr = Al, Ga, In; T = Si, Ge, Sn) and N-base (N-base = HCN, NH3, CN\u2212)","volume":"1201","author":"Wang","year":"2021","journal-title":"Comput. Theor. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1107\/S2052520616003954","article-title":"The Cambridge Structural Database","volume":"72","author":"Groom","year":"2016","journal-title":"Acta Crystallogr. B"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1874","DOI":"10.1021\/acs.organomet.1c00203","article-title":"Reactivity of (TMS)2N(\u03b71-Cp*) Si=Si (\u03b71-Cp*)N(TMS)2 toward the Halides of Groups 13\u201315","volume":"40","author":"Sen","year":"2021","journal-title":"Organometallics"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"e26526","DOI":"10.1002\/qua.26526","article-title":"Unusual substituent effects in the Tr\u00b7\u00b7\u00b7 Te triel bond","volume":"121","author":"Wang","year":"2021","journal-title":"Int. J. Quantum Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"e26046","DOI":"10.1002\/qua.26046","article-title":"Comparison of triel bonds with different chalcogen electron donors: Its dependence on triel donor and methyl substitution","volume":"120","author":"Chi","year":"2019","journal-title":"Int. J. Quantum Chem."},{"key":"ref_63","first-page":"074304","article-title":"Effect of carbon hybridization in C\u2014F bond as an electron donor in triel bonds","volume":"153","author":"Yang","year":"2020","journal-title":"Chem. Phys."},{"key":"ref_64","doi-asserted-by":"crossref","unstructured":"Wojtkowiak, K., and Jezierska, A. (2022). Exploring the Dynamical Nature of Intermolecular Hydrogen Bonds in Benzamide, Quinoline and Benzoic Acid Derivatives. Molecules, 27.","DOI":"10.3390\/molecules27248847"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1039\/C39950000113","article-title":"Geometric and electric properties of the donor-acceptor complex H 3N-BF3","volume":"1","author":"Fujiang","year":"1995","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/S0009-2614(98)00036-0","article-title":"Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities","volume":"285","author":"Espinosa","year":"1998","journal-title":"Chem. Phys. Lett."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1016\/j.ccr.2004.08.022","article-title":"Complementarity of QTAIM and MO theory in the study of bonding in donor\u2013acceptor complexes","volume":"249","author":"Bader","year":"2005","journal-title":"Coord. Chem. Rev."},{"key":"ref_68","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_69","doi-asserted-by":"crossref","first-page":"0618","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_70","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_71","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 Rev. C.01, Gaussian, Inc."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"4939","DOI":"10.1021\/acs.jpca.5b12571","article-title":"Rotational study of dimethyl ether\u2013chlorotrifluoroethylene: Lone pair\u00b7\u00b7\u00b7 \u03c0 interaction links the two subunits","volume":"120","author":"Spada","year":"2016","journal-title":"Phys. Chem. A"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"13820","DOI":"10.1039\/C6CP01703G","article-title":"\u201cPnicogen bonds\u201d or \u201cchalcogen bonds\u201d: Exploiting the effect of substitution on the formation of P\u22ef Se noncovalent bonds","volume":"18","author":"Shukla","year":"2016","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"21","DOI":"10.1016\/j.comptc.2015.07.024","article-title":"Non-additivity of F substituent in enhancing the halogen bond in C6H5I\u22ef NCH","volume":"1070","author":"Tang","year":"2015","journal-title":"Comput. Theor. Chem."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"5597","DOI":"10.1021\/acs.jpca.5b02283","article-title":"Expanding lone pair\u00b7\u00b7\u00b7 \u03c0 interactions to nonaromatic systems and nitrogen bases: Complexes of C2F3X (X = F, Cl, Br, I) and TMA-d 9","volume":"119","author":"Geboes","year":"2015","journal-title":"J. Phys. Chem. A"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"553","DOI":"10.1080\/00268977000101561","article-title":"Calculation of Small Molecular Interactions by Differences of Separate Total Energies - Some Procedures with Reduced Errors","volume":"19","author":"Boys","year":"1970","journal-title":"Mol. Phys."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"314","DOI":"10.1016\/j.jmgm.2012.07.004","article-title":"Quantitative analysis of molecular surface based on improved Marching Tetrahedra algorithm","volume":"38","author":"Lu","year":"2012","journal-title":"Mol. Graph. Model."},{"key":"ref_78","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":"Comput. Chem."},{"key":"ref_79","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":"Mol. Graph. Model."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1107\/S0021889807067908","article-title":"Mercury CSD 2.0\u2014New features for the visualization and investigation of crystal structures","volume":"41","author":"Macrae","year":"2008","journal-title":"J. Appl. Crystallogr."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"389","DOI":"10.1107\/S0108768102003324","article-title":"New software for searching the Cambridge Structural Database and visualizing crystal structures","volume":"58","author":"Bruno","year":"2002","journal-title":"Acta Crystallogr. B Struct. Sci. Cryst. Eng. Mater."},{"key":"ref_82","first-page":"024109","article-title":"Sparse maps\u2014A systematic infrastructure for reduced-scaling electronic structure methods. II. Linear scaling domain based pair natural orbital coupled cluster theory","volume":"144","author":"Riplinger","year":"2016","journal-title":"Chem. Phys."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"6796","DOI":"10.1063\/1.462569","article-title":"Electron affinities of the first-row atoms revisited. Systematic basis sets and wave functions","volume":"96","author":"Kendall","year":"1992","journal-title":"J. Chem. Phys."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1002\/wcms.81","article-title":"The ORCA program system","volume":"2","author":"Neese","year":"2012","journal-title":"Wires Comput. Mol. Sci."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"1887","DOI":"10.1021\/cr00031a008","article-title":"Perturbation theory approach to intermolecular potential energy surfaces of van der Waals complexes","volume":"94","author":"Jeziorski","year":"1994","journal-title":"Chem. Rev."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"014101","DOI":"10.1063\/1.3451077","article-title":"Density fitting of intramonomer correlation effects in symmetry-adapted perturbation theory","volume":"132","author":"Hohenstein","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"184108","DOI":"10.1063\/5.0006002","article-title":"PSI4 1.4: Open-source software for high-throughput quantum chemistry","volume":"152","author":"Smith","year":"2020","journal-title":"J. Chem. Phys."},{"key":"ref_88","doi-asserted-by":"crossref","unstructured":"Marx, D., and Hutter, J. (2009). Ab Initio Molecular Dynamics: Basic Theory and Advanced Methods, Cambridge University Press.","DOI":"10.1017\/CBO9780511609633"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"1396","DOI":"10.1103\/PhysRevLett.78.1396","article-title":"Erratum: Generalized gradient approximation made simple (Physical Review Letters (1996) 77 (3865))","volume":"78","author":"Perdew","year":"1997","journal-title":"Phys. Rev. Lett."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"154104","DOI":"10.1063\/1.3382344","article-title":"A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu","volume":"132","author":"Grimme","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"1456","DOI":"10.1002\/jcc.21759","article-title":"Effect of the damping function in dispersion corrected density functional theory","volume":"32","author":"Grimme","year":"2011","journal-title":"Comput. Chem."},{"key":"ref_92","first-page":"114105","article-title":"Gaussian basis sets for accurate calculations on molecular systems in gas and condensed phases","volume":"127","author":"VandeVondele","year":"2007","journal-title":"Chem. Phys."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"1703","DOI":"10.1103\/PhysRevB.54.1703","article-title":"Separable dual-space Gaussian pseudopotentials","volume":"54","author":"Goedecker","year":"1996","journal-title":"Phys. Rev. B"},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"3641","DOI":"10.1103\/PhysRevB.58.3641","article-title":"Relativistic separable dual-space Gaussian pseudopotentials from H to Rn","volume":"58","author":"Hartwigsen","year":"1998","journal-title":"Phys. Rev. B"},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"2348","DOI":"10.1021\/ct1002225","article-title":"Auxiliary density matrix methods for Hartree\u2013Fock exchange calculations","volume":"6","author":"Guidon","year":"2010","journal-title":"Chem. Theory Comput."},{"key":"ref_96","first-page":"074105","article-title":"Efficient solution of Poisson\u2019s equation with free boundary conditions","volume":"125","author":"Genovese","year":"2006","journal-title":"Chem. Phys."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1002\/wcms.1159","article-title":"cp2k: Atomistic simulations of condensed matter systems","volume":"4","author":"Hutter","year":"2014","journal-title":"Wires Comput. Mol. Sci."},{"key":"ref_98","unstructured":"Keith, A.T. (2014). AIMAll (Version 14.11.23), TK Gristmill Software."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/9\/7881\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T19:23:32Z","timestamp":1760124212000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/9\/7881"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,4,26]]},"references-count":98,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2023,5]]}},"alternative-id":["ijms24097881"],"URL":"https:\/\/doi.org\/10.3390\/ijms24097881","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2023,4,26]]}}}