{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T12:08:05Z","timestamp":1790770085903,"version":"4.1.0"},"reference-count":73,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2024,7,29]],"date-time":"2024-07-29T00:00:00Z","timestamp":1722211200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001824","name":"Czech Science Foundation","doi-asserted-by":"publisher","award":["24-15057L"],"award-info":[{"award-number":["24-15057L"]}],"id":[{"id":"10.13039\/501100001824","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The benzene dimer (BD) is an archetypal model of \u03c0\u2219\u2219\u2219\u03c0 and C\u2013H\u2219\u2219\u2219\u03c0 noncovalent interactions as they occur in its cofacial and perpendicular arrangements, respectively. The enthalpic stabilization of the related BD structures has been debated for a long time and is revisited here. The revisit is based on results of computations that apply the coupled-cluster theory with singles, doubles and perturbative triples [CCSD(T)] together with large basis sets and extrapolate results to the complete basis set (CBS) limit in order to accurately characterize the three most important stationary points of the intermolecular interaction energy (\u0394E) surface of the BD, which correspond to the tilted T-shaped (TT), fully symmetric T-shaped (FT) and slipped-parallel (SP) structures. In the optimal geometries obtained by searching extensive sets of the CCSD(T)\/CBS \u0394E data of the TT, FT and SP arrangements, the resulting \u0394E values were \u221211.84, \u221211.34 and \u221211.21 kJ\/mol, respectively. The intrinsic strength of the intermolecular bonding in these configurations was evaluated by analyzing the distance dependence of the CCSD(T)\/CBS \u0394E data over wide ranges of intermonomer separations. In this way, regions of the relative distances that favor BD structures with either \u03c0\u2219\u2219\u2219\u03c0 or C\u2013H\u2219\u2219\u2219\u03c0 interactions were found and discussed in a broader context.<\/jats:p>","DOI":"10.3390\/ijms25158272","type":"journal-article","created":{"date-parts":[[2024,7,30]],"date-time":"2024-07-30T17:08:34Z","timestamp":1722359314000},"page":"8272","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":14,"title":["Revisiting the Most Stable Structures of the Benzene Dimer"],"prefix":"10.3390","volume":"25","author":[{"given":"Ji\u0159\u00ed","family":"Czernek","sequence":"first","affiliation":[{"name":"Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovsky Square 2, 162 00 Prague, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2692-612X","authenticated-orcid":false,"given":"Ji\u0159\u00ed","family":"Brus","sequence":"additional","affiliation":[{"name":"Institute of Macromolecular Chemistry, Czech Academy of Sciences, Heyrovsky Square 2, 162 00 Prague, Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,7,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Karshikoff, A. (2021). Non-Covalent Interactions in Proteins, World Scientific. [2nd ed.].","DOI":"10.1142\/12035"},{"key":"ref_2","first-page":"e202304010","article-title":"Boosting Energy-Transfer Processes via Dispersion Interactions","volume":"29","author":"Cerveri","year":"2023","journal-title":"Chem. Eur. J."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1770","DOI":"10.1038\/s41467-022-29299-0","article-title":"The promotion effect of \u03c0-\u03c0 interactions in Pd NPs catalysed selective hydrogenation","volume":"13","author":"Guo","year":"2022","journal-title":"Nat. Commun."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2310838","DOI":"10.1002\/smll.202310838","article-title":"Self-Assembled Nanocarrier Delivery Systems for Bioactive Compounds","volume":"20","author":"Zhang","year":"2024","journal-title":"Small"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"107330","DOI":"10.1016\/j.isci.2023.107330","article-title":"Crystal engineering of high explosives through lone pair-\u03c0 interactions: Insights for improving thermal safety","volume":"26","author":"Savastano","year":"2023","journal-title":"iScience"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"6937","DOI":"10.1021\/acs.nanolett.3c01540","article-title":"Cooperative Self-Assembly of Dimer Junctions Driven by \u03c0 Stacking Leads to Conductance Enhancement","volume":"23","author":"Pan","year":"2023","journal-title":"Nano Lett."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1021\/acsenergylett.0c02604","article-title":"Synergistic Effect of Hydrogen Bonding and \u03c0\u2013\u03c0 Stacking Enables Long Cycle Life in Organic Electrode Materials","volume":"6","author":"Tuttle","year":"2021","journal-title":"ACS Energy Lett."},{"key":"ref_8","first-page":"24836","article-title":"The Energetic Origins of Pi-Pi Contacts in Proteins","volume":"145","author":"Liu","year":"2023","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1365","DOI":"10.1038\/s41557-023-01291-1","article-title":"C\u2013H\u00b7\u00b7\u00b7\u03c0 interactions disrupt electrostatic interactions between non-aqueous electrolytes to increase solubility","volume":"15","author":"Samaroo","year":"2023","journal-title":"Nat. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"4824","DOI":"10.1039\/D2CP04335A","article-title":"A critical comparison of CH\u00b7\u00b7\u00b7\u03c0 versus \u03c0\u00b7\u00b7\u00b7\u03c0 interactions in the benzene dimer: Obtaining benchmarks at the CCSD(T) level and assessing the accuracy of lower scaling methods","volume":"25","author":"Herman","year":"2023","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"201102","DOI":"10.1063\/1.4834855","article-title":"Communication: Benzene dimer\u2014The free energy landscape","volume":"139","author":"Tummanapelli","year":"2013","journal-title":"J. Chem. Phys."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"227101","DOI":"10.1063\/1.4882015","article-title":"Comment on \u201cCommunication: Benzene dimer\u2014The free energy landscape\u201d [J. Chem. Phys. 139, 201102 (2013)]","volume":"140","author":"Podeszwa","year":"2014","journal-title":"J. Chem. Phys."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"227102","DOI":"10.1063\/1.4882016","article-title":"Response to \u201cComment on \u2018Communication: Benzene dimer\u2014The free energy landscape\u2019\u201d [J. Chem. Phys. 140, 227101 (2014)]","volume":"140","author":"Tummanapelli","year":"2014","journal-title":"J. Chem. Phys."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"4871","DOI":"10.1063\/1.447514","article-title":"Dimers of aromatic molecules: (Benzene)2, (toluene)2, and benzene\u2013toluene","volume":"81","author":"Law","year":"1984","journal-title":"J. Chem. Phys."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"4294","DOI":"10.1063\/1.465035","article-title":"The rotational spectrum, structure and dynamics of a benzene dimer","volume":"98","author":"Arunan","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"171101","DOI":"10.1063\/1.2198828","article-title":"An experimental value for the B1u C\u2013H stretch mode in benzene","volume":"124","author":"Erlekam","year":"2006","journal-title":"J. Chem. Phys."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3446","DOI":"10.1021\/jp068635t","article-title":"Understanding of Assembly Phenomena by Aromatic\u2212Aromatic Interactions:\u2009 Benzene Dimer and the Substituted Systems","volume":"111","author":"Lee","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"8219","DOI":"10.1039\/c002653k","article-title":"Vibration\u2013rotation-tunneling states of the benzene dimer: An ab initio study","volume":"12","author":"Podeszwa","year":"2010","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5180","DOI":"10.1002\/anie.201300653","article-title":"Structure of the Benzene Dimer\u2014Governed by Dynamics","volume":"52","author":"Schnell","year":"2013","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3108","DOI":"10.1002\/anie.201812556","article-title":"Rotational Signatures of Dispersive Stacking in the Formation of Aromatic Dimers","volume":"58","author":"Fatima","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3233","DOI":"10.1021\/j100296a026","article-title":"Dissociation Energies of the Benzene Dimer and Dimer Cation","volume":"91","author":"Grover","year":"1987","journal-title":"J. Phys. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"411","DOI":"10.1016\/0009-2614(91)80010-U","article-title":"Binding energies of small benzene clusters","volume":"184","author":"Krause","year":"1991","journal-title":"Chem. Phys. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1203","DOI":"10.1021\/acs.chemrev.0c00006","article-title":"Many-Body Quantum Chemistry on Massively Parallel Computers","volume":"121","author":"Calvin","year":"2021","journal-title":"Chem. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"e1452","DOI":"10.1002\/wcms.1452","article-title":"Recent developments in symmetry-adapted perturbation theory","volume":"10","author":"Patkowski","year":"2020","journal-title":"Wiley Interdiscip. Rev. Comput. Mol. Sci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"25","DOI":"10.1007\/s00214-019-2414-5","article-title":"Evaluation of methods for obtaining dispersion energies used in density functional calculations of intermolecular interactions","volume":"138","author":"Shahbaz","year":"2019","journal-title":"Theor. Chem. Acc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"3679","DOI":"10.1021\/acs.accounts.1c00387","article-title":"Predicting and Understanding Non-Covalent Interactions Using Novel Forms of Symmetry-Adapted Perturbation Theory","volume":"54","author":"Lao","year":"2021","journal-title":"Acc. Chem. Res."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"170401","DOI":"10.1063\/5.0053674","article-title":"Frontiers of stochastic electronic structure calculations","volume":"154","author":"Jordan","year":"2021","journal-title":"J. Chem. Phys."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3927","DOI":"10.1038\/s41467-021-24119-3","article-title":"Interactions between large molecules pose a puzzle for reference quantum mechanical methods","volume":"12","author":"Nagy","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"886","DOI":"10.1002\/wcms.1110","article-title":"Spin-component-scaled electron correlation methods","volume":"2","author":"Grimme","year":"2012","journal-title":"Wiley Interdiscip. Rev. Comput. Mol. Sci."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"7568","DOI":"10.1021\/jp5024235","article-title":"Benchmark Theoretical Study of the \u03c0\u2013\u03c0 Binding Energy in the Benzene Dimer","volume":"118","author":"Miliordos","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6758","DOI":"10.1039\/D0SC02667K","article-title":"Electrostatics does not dictate the slip-stacked arrangement of aromatic \u03c0\u2013\u03c0 interactions","volume":"11","author":"Herbert","year":"2020","journal-title":"Chem. Sci."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Czernek, J., Brus, J., Czernekov\u00e1, V., and Kobera, L. (2023). Quantifying the Intrinsic Strength of C\u2013H\u22efO Intermolecular Interactions. Molecules, 28.","DOI":"10.3390\/molecules28114478"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"442","DOI":"10.1038\/s41467-020-20212-1","article-title":"Dynamical strengthening of covalent and non-covalent molecular interactions by nuclear quantum effects at finite temperature","volume":"12","author":"Sauceda","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"7025","DOI":"10.1038\/s41467-021-27324-2","article-title":"Parallel-stacked aromatic molecules in hydrogen-bonded inorganic frameworks","volume":"12","author":"Igarashi","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1827","DOI":"10.1021\/acsami.2c17728","article-title":"Hydroxy-Containing Covalent Organic Framework Combined with Nickel Ferrite as a Platform for the Recognition and Capture of Bisphenols","volume":"15","author":"Di","year":"2023","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"4025","DOI":"10.1039\/D3NR05130G","article-title":"Elucidating the reversible and irreversible self-assembly mechanisms of low-complexity aromatic-rich kinked peptides and steric zipper peptides","volume":"16","author":"Lao","year":"2024","journal-title":"Nanoscale"},{"key":"ref_37","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_38","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_39","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_40","doi-asserted-by":"crossref","unstructured":"Czernek, J., Brus, J., and Czernekov\u00e1, V. (2022). A Cost Effective Scheme for the Highly Accurate Description of Intermolecular Binding in Large Complexes. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms232415773"},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Czernek, J., and Brus, J. (2023). On the Intermolecular Interactions in Thiophene-Cored Single-Stacking Junctions. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms241713349"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Czernek, J., and Brus, J. (2024). Reliable Dimerization Energies for Modeling of Supramolecular Junctions. Int. J. Mol. Sci., 25.","DOI":"10.3390\/ijms25010602"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"10345","DOI":"10.1021\/jp064095o","article-title":"Potential Energy Surface for the Benzene Dimer and Perturbational Analysis of \u03c0\u2212\u03c0 Interactions","volume":"110","author":"Podeszwa","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1016\/0022-2860(76)87003-2","article-title":"Molecular structure of benzene","volume":"30","author":"Tamagawa","year":"1976","journal-title":"J. Mol. Struct."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"014103","DOI":"10.1063\/5.0133026","article-title":"\u03c9B97X-3c: A composite range-separated hybrid DFT method with a molecule-optimized polarized valence double-\u03b6 basis set","volume":"158","author":"Hansen","year":"2023","journal-title":"J. Chem. Phys."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1135","DOI":"10.1055\/s-0042-1753141","article-title":"Efficient Computation of the Interaction Energies of Very Large Non-covalently Bound Complexes","volume":"34","author":"Gorges","year":"2023","journal-title":"Synlett"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2427","DOI":"10.1021\/ct2002946","article-title":"S66: A Well-balanced Database of Benchmark Interaction Energies Relevant to Biomolecular Structures","volume":"7","author":"Riley","year":"2011","journal-title":"J. Chem. Theory Comput."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"244106","DOI":"10.1063\/5.0155895","article-title":"A quantitative assessment of deformation energy in intermolecular interactions: How important is it?","volume":"158","author":"Sargent","year":"2023","journal-title":"J. Chem. Phys."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2357","DOI":"10.1021\/acs.jpca.4c00541","article-title":"Strengthening of Noncovalent Bonds Caused by Internal Deformations","volume":"128","author":"Scheiner","year":"2024","journal-title":"J. Phys. Chem. A"},{"key":"ref_50","unstructured":"Stone, A.J. (2002). The Theory of Intermolecular Forces, Clarendon Press. [1st ed.]."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"24870","DOI":"10.1039\/D0CP05039C","article-title":"Reinterpreting \u03c0-stacking","volume":"22","author":"Herbert","year":"2020","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"8979","DOI":"10.1039\/D2CP00714B","article-title":"Electrostatic penetration effects stand at the heart of aromatic \u03c0 interactions","volume":"24","year":"2022","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"e31476","DOI":"10.7554\/eLife.31486","article-title":"Pi-Pi contacts are an overlooked protein feature relevant to phase separation","volume":"7","author":"Vernon","year":"2018","journal-title":"eLife"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1016\/S0009-2614(98)00111-0","article-title":"Basis-set convergence in correlated calculations on Ne, N2, and H2O","volume":"286","author":"Halkier","year":"1998","journal-title":"Chem. Phys. Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"184107","DOI":"10.1063\/5.0004635","article-title":"TURBOMOLE: Modular program suite for ab initio quantum-chemical and condensed-matter simulations","volume":"152","author":"Balasubramani","year":"2020","journal-title":"J. Chem. Phys."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"331","DOI":"10.1007\/s002140050269","article-title":"RI-MP2: First derivatives and global consistency","volume":"97","author":"Weigend","year":"1997","journal-title":"Theor. Chem. Acc."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1016\/S0009-2614(98)00862-8","article-title":"RI-MP2: Optimized auxiliary basis sets and demonstration of efficiency","volume":"294","author":"Weigend","year":"1998","journal-title":"Chem. Phys. Lett."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"144107","DOI":"10.1063\/5.0005081","article-title":"The Molpro quantum chemistry package","volume":"152","author":"Werner","year":"2020","journal-title":"J. Chem. Phys."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"014103","DOI":"10.1063\/1.1824898","article-title":"Density-functional theory-symmetry-adapted intermolecular perturbation theory with density fitting: A new efficient method to study intermolecular interaction energies","volume":"122","author":"Jansen","year":"2005","journal-title":"J. Chem. Phys."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"204303","DOI":"10.1063\/5.0093557","article-title":"A computational inspection of the dissociation energy of mid-sized organic dimers","volume":"156","author":"Czernek","year":"2022","journal-title":"J. Chem. Phys."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1016\/S0009-2614(02)00538-9","article-title":"First-order intermolecular interaction energies from Kohn\u2013Sham orbitals","volume":"357","author":"Jansen","year":"2002","journal-title":"Chem. Phys. Lett."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"778","DOI":"10.1016\/S0009-2614(02)01796-7","article-title":"Intermolecular dispersion energies from time-dependent density functional theory","volume":"367","author":"Jansen","year":"2003","journal-title":"Chem. Phys. Lett."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"319","DOI":"10.1016\/S0009-2614(02)01097-7","article-title":"Intermolecular induction and exchange-induction energies from coupled-perturbed Kohn\u2013Sham density functional theory","volume":"362","author":"Jansen","year":"2002","journal-title":"Chem. Phys. Lett."},{"key":"ref_64","first-page":"741","article-title":"Symmetry-adapted perturbation theory for the calculation of Hartree\u2013Fock interaction energies","volume":"88","author":"Moszynski","year":"1996","journal-title":"Mol. Phys."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"6158","DOI":"10.1063\/1.478522","article-title":"Toward reliable density functional methods without adjustable parameters: The PBE0 model","volume":"110","author":"Adamo","year":"1999","journal-title":"J. Chem. Phys."},{"key":"ref_66","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_67","doi-asserted-by":"crossref","first-page":"3297","DOI":"10.1039\/b508541a","article-title":"Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy","volume":"7","author":"Weigend","year":"2005","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_68","unstructured":"Frish, M.J., Trucks, J.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Petersson, G.A., and Nakatsuji, H. (2019). Gaussian 16; Revision C.01, Gaussian, Inc."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"e1606","DOI":"10.1002\/wcms.1606","article-title":"Software update: The ORCA program system\u2014Version 5.0","volume":"12","author":"Neese","year":"2022","journal-title":"Wiley Interdiscip. Rev. Comput. Mol. Sci."},{"key":"ref_70","unstructured":"ORCA4wB97X-3c (2024, June 28). A Fortran Script for Setting Up a \u03c9B97X-3c Calculation with ORCA 5.0.3 or Higher. Available online: https:\/\/github.com\/grimme-lab\/ORCA4wB97X-3c."},{"key":"ref_71","doi-asserted-by":"crossref","unstructured":"Bende, A., and Farca\u015f, A.-A. (2023). Intermolecular-Type Conical Intersections in Benzene Dimer. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24032906"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"3524","DOI":"10.1021\/acs.jctc.3c00769","article-title":"Scalable Quantum Monte Carlo with Direct-Product Trial Wave Functions","volume":"20","author":"Pham","year":"2024","journal-title":"J. Chem. Theory Comput."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"015054","DOI":"10.1088\/2632-2153\/ad2cef","article-title":"Optimized multifidelity machine learning for quantum chemistry","volume":"5","author":"Vinod","year":"2024","journal-title":"Mach. Learn. Sci. Technol."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/25\/15\/8272\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T15:25:54Z","timestamp":1760109954000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/25\/15\/8272"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,7,29]]},"references-count":73,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2024,8]]}},"alternative-id":["ijms25158272"],"URL":"https:\/\/doi.org\/10.3390\/ijms25158272","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,7,29]]}}}