{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T19:59:37Z","timestamp":1790798377579,"version":"4.1.0"},"reference-count":53,"publisher":"American Chemical Society (ACS)","issue":"35","license":[{"start":{"date-parts":[[2026,8,23]],"date-time":"2026-08-23T00:00:00Z","timestamp":1787443200000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/creativecommons.org\/licenses\/by-nc-nd\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["528562393 - FIP 26"],"award-info":[{"award-number":["528562393 - FIP 26"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2025,9,4]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The benzene\u00b7\u00b7\u00b7methanol dimer is one of the simplest systems that manifests an O\u2013H\u00b7\u00b7\u00b7\u03c0 nonbonded interaction. This interaction can be found in numerous systems, ranging from small-molecule clusters to biological systems, for example, phenyl-containing ligands bound within a protein\u2019s binding pocket. Herein, four gas-phase configurations are examined using quantum mechanics, which have O\u2013H\u00b7\u00b7\u00b7\u03c0, CH3\u00b7\u00b7\u00b7\u03c0 and Bz\u2013H\u00b7\u00b7\u00b7O interactions. Geometry optimization and frequency calculations were performed up to the MP2\/aug-cc-pVQZ theory level, with electronic energies obtained up to the CCSD(T)\/complete basis set (CBS) limit. Considering the electronic energy (\u0394Eel), the O\u2013H\u00b7\u00b7\u00b7\u03c0 configuration is the most stable, with a CCSD(T)\/CBS (counterpoise corrected) interaction energy of \u22124.09 kcal mol\u20131, while the other three configurations ranged from \u22122.00 to \u22122.60 kcal mol\u20131. Using scaled harmonic frequencies, the temperature influence was investigated by computing Gibbs relative and interaction free energies over a 10\u2013800 K temperature range.<\/jats:p>","DOI":"10.1021\/acs.jpca.5c03923","type":"journal-article","created":{"date-parts":[[2025,8,23]],"date-time":"2025-08-23T13:53:48Z","timestamp":1755957228000},"page":"8110-8119","source":"Crossref","is-referenced-by-count":0,"title":["Gas-Phase Benzene\u2013Methanol\nDimer Configurations:\nGeometries, Relative Stabilities, and Interaction Energies"],"prefix":"10.1021","volume":"129","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4581-920X","authenticated-orcid":true,"given":"Karl N.","family":"Kirschner","sequence":"first","affiliation":[{"name":"University of Applied Sciences Bonn-Rhein-Sieg , , Grantham-Allee 20 , ,","place":["Sankt Augustin, Germany, 53757"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2025,8,23]]},"reference":[{"key":"2026093015094718800_cit1","doi-asserted-by":"publisher","first-page":"4145","DOI":"10.1021\/cr990051i","article-title":"Molecular Clusters of \u03c0-Systems:\nTheoretical Studies of Structures, Spectra, and Origin of Interaction\nEnergies","volume":"100","author":"Kim","year":"2000","journal-title":"Chem. Rev."},{"key":"2026093015094718800_cit2","doi-asserted-by":"publisher","first-page":"5900","DOI":"10.1038\/s41467-023-41451-y","article-title":"Strong Structuring\nArising from Weak Cooperative O-H\u00b7\u00b7\u00b7\u03c0 and C-H\u00b7\u00b7\u00b7O\nHydrogen Bonding in Benzene-methanol Solution","volume":"14","author":"Di Mino","year":"2023","journal-title":"Nat. Commun."},{"key":"2026093015094718800_cit3","doi-asserted-by":"publisher","first-page":"10556","DOI":"10.1021\/jp206248w","article-title":"Coordination\nof Methanol Clusters to Benzene: A Computational Study","volume":"115","author":"Matisz","year":"2011","journal-title":"J. Phys. Chem. A"},{"key":"2026093015094718800_cit4","doi-asserted-by":"publisher","first-page":"2427","DOI":"10.1021\/ct2002946","article-title":"S66: A Well-balanced Database of\nBenchmark Interaction Energies Relevant to Biomolecular Structures","volume":"7","author":"R\u030ceza\u0301c\u030c","year":"2011","journal-title":"J. Chem. Theory Comput."},{"key":"2026093015094718800_cit5","doi-asserted-by":"publisher","first-page":"1359","DOI":"10.1021\/ct5000692","article-title":"Erratum to \u201cS66: A Well-balanced\nDatabase of Benchmark Interaction Energies Relevant to Biomolecular\nStructures\u201d","volume":"10","author":"R\u030ceza\u0301c\u030c","year":"2014","journal-title":"J. Chem. Theory Comput."},{"key":"2026093015094718800_cit6","doi-asserted-by":"publisher","first-page":"20790","DOI":"10.1039\/C6CP01787H","article-title":"Non-covalent interaction of benzene with methanol and\ndiethyl ether solid surfaces","volume":"18","author":"Marchione","year":"2016","journal-title":"Phys. Chem. Chem.\nPhys."},{"key":"2026093015094718800_cit7","doi-asserted-by":"publisher","first-page":"2145","DOI":"10.1063\/1.473784","article-title":"Resonant ion-dip infrared spectroscopy\nof benzene-(methanol)m clusters with m = 1\u20136","volume":"106","author":"Pribble","year":"1997","journal-title":"J. Chem. Phys."},{"key":"2026093015094718800_cit8","doi-asserted-by":"publisher","first-page":"496","DOI":"10.1021\/jp983629l","article-title":"C\u2013H Stretch\nModes as a Probe of H-Bonding in\nMethanol-Containing Clusters","volume":"103","author":"Gruenloh","year":"1999","journal-title":"J. Phys. Chem.\nA"},{"key":"2026093015094718800_cit9","doi-asserted-by":"publisher","first-page":"1844","DOI":"10.1063\/1.480748","article-title":"Fluorobenzene and p-difluorobenzene\nmicrosolvated by methanol: An infrared spectroscopic and ab initio\ntheoretical investigation","volume":"112","author":"Buchhold","year":"2000","journal-title":"J. Chem. Phys."},{"key":"2026093015094718800_cit10","doi-asserted-by":"publisher","first-page":"18917","DOI":"10.1021\/jp076538+","article-title":"Ab Initio Modeling of Methanol Interaction with Single-Walled\nCarbon Nanotubes","volume":"111","author":"Pankewitz","year":"2007","journal-title":"J. Phys. Chem. 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Phys. Chem. A"},{"key":"2026093015094718800_cit36","doi-asserted-by":"publisher","first-page":"103","DOI":"10.1002\/jrs.1250080208","article-title":"The totally\nsymmetric rotation-vibrational Raman bands\nof benzene","volume":"8","author":"Jensen","year":"1979","journal-title":"J. Raman Spectrosc."},{"key":"2026093015094718800_cit37","doi-asserted-by":"publisher","first-page":"209","DOI":"10.1016\/0022-2852(82)90284-3","article-title":"The spectrum of benzene in the 3-\u03bcm region: The\n\u03bd12 fundamental band","volume":"93","author":"Pli\u0301va","year":"1982","journal-title":"J. Mol.\nSpectrosc."},{"key":"2026093015094718800_cit38","doi-asserted-by":"publisher","first-page":"269","DOI":"10.1139\/p83-037","article-title":"The \u03bd13 fundamental band of benzene","volume":"61","author":"Pli\u0301va","year":"1983","journal-title":"Can.\nJ. Phys."},{"key":"2026093015094718800_cit39","doi-asserted-by":"publisher","first-page":"318","DOI":"10.1016\/0022-2852(84)90011-0","article-title":"The perpendicular\nband \u03bd14 of benzene\nnear 10 \u03bcm","volume":"107","author":"Pli\u0301va","year":"1984","journal-title":"J. Mol. Spectrosc."},{"key":"2026093015094718800_cit40","doi-asserted-by":"publisher","first-page":"3311","DOI":"10.1063\/1.449190","article-title":"Ionization-detected\nRaman studies\nof the 1600 cm\u20131 Fermi dyad of benzene","volume":"83","author":"Esherick","year":"1985","journal-title":"J. Chem. Phys."},{"key":"2026093015094718800_cit41","doi-asserted-by":"publisher","first-page":"1479","DOI":"10.1063\/1.453257","article-title":"The a2g mode in ground state benzene","volume":"87","author":"Berman","year":"1987","journal-title":"J. Chem.\nPhys."},{"key":"2026093015094718800_cit42","doi-asserted-by":"publisher","first-page":"269","DOI":"10.1006\/jmsp.1993.1232","article-title":"High-Resolution\nStudy of the Difference\nBand \u03bd17 - \u03bd20 of Benzene","volume":"161","author":"Pliva","year":"1993","journal-title":"J. Mol. Spectrosc."},{"key":"2026093015094718800_cit43","first-page":"859","article-title":"The difference\nbands \u03bd11-\u03bd4 and \u03bd10-\u03bd18 of benzene at high resolution","volume":"87","author":"Pli\u0301va","year":"1996","journal-title":"Mol.\nPhys."},{"key":"2026093015094718800_cit44","doi-asserted-by":"publisher","first-page":"83","DOI":"10.1016\/S0009-2614(97)00490-9","article-title":"The \u03bd6, \u03bd7, \u03bd8 and \u03bd19 gas phase fundamental\nfrequencies of 12C6H6","volume":"272","author":"Cane\u0301","year":"1997","journal-title":"Chem. Phys. Lett."},{"key":"2026093015094718800_cit45","doi-asserted-by":"publisher","first-page":"414","DOI":"10.1016\/S0009-2614(97)00735-5","article-title":"The harmonic\nfrequencies of benzene.\nA case for atomic natural orbital basis sets","volume":"275","author":"Martin","year":"1997","journal-title":"Chem. Phys. Lett."},{"key":"2026093015094718800_cit46","doi-asserted-by":"publisher","first-page":"3687","DOI":"10.1021\/acs.jctc.1c00249","article-title":"Transfer Learning to\nCCSD(T): Accurate Anharmonic Frequencies from Machine Learning Models","volume":"17","author":"Ka\u0308ser","year":"2021","journal-title":"J. Chem. Theory Comput."},{"key":"2026093015094718800_cit47","doi-asserted-by":"publisher","first-page":"4768","DOI":"10.1021\/ja00168a022","article-title":"Aromatic-aromatic interactions: free energy profiles\nfor the benzene dimer in water, chloroform, and liquid benzene","volume":"112","author":"Jorgensen","year":"1990","journal-title":"J. Am. Chem. Soc."},{"key":"2026093015094718800_cit48","doi-asserted-by":"publisher","first-page":"7245","DOI":"10.1063\/1.462429","article-title":"Multiphoton ionization studies of\nC6H6-(CH3OH)n clusters.\nI. Comparisons with C6H6-(H2O)n clusters","volume":"96","author":"Garrett","year":"1992","journal-title":"J. Chem. Phys."},{"key":"2026093015094718800_cit49","doi-asserted-by":"publisher","first-page":"141102","DOI":"10.1063\/1.2795693","article-title":"The origin of deficiency of the supermolecule second-order\nM\u00f8ller-Plesset approach for evaluating interaction energies","volume":"127","author":"Cybulski","year":"2007","journal-title":"J. Chem. Phys."},{"key":"2026093015094718800_cit50","doi-asserted-by":"publisher","first-page":"282","DOI":"10.1002\/cphc.200800718","article-title":"Scaled MP3\nNon-Covalent Interaction Energies Agree Closely with Accurate CCSD(T)\nBenchmark Data","volume":"10","author":"Piton\u030ca\u0301k","year":"2009","journal-title":"ChemPhysChem"},{"key":"2026093015094718800_cit51","doi-asserted-by":"publisher","first-page":"141","DOI":"10.1016\/0166-1280(93)87071-K","article-title":"An evaluation of AM1 calculated vibrational frequencies","volume":"281","author":"Healy","year":"1993","journal-title":"Journal of Molecular Structure: THEOCHEM"},{"key":"2026093015094718800_cit52","doi-asserted-by":"publisher","first-page":"9342","DOI":"10.1021\/ja0630285","article-title":"Popular Theoretical Methods Predict\nBenzene and Arenes\nTo Be Nonplanar","volume":"128","author":"Moran","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"2026093015094718800_cit53","doi-asserted-by":"publisher","first-page":"230","DOI":"10.1016\/j.cplett.2016.12.047","article-title":"Comment on a spurious prediction of a non-planar geometry\nfor benzene at the MP2 level of theory","volume":"669","author":"Samala","year":"2017","journal-title":"Chem.\nPhys. Lett."}],"container-title":["The Journal of Physical\nChemistry A"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jpca.5c03923","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article-pdf\/129\/35\/8110\/67240742\/acs.jpca.5c03923.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article-pdf\/129\/35\/8110\/67240742\/acs.jpca.5c03923.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T19:24:26Z","timestamp":1790796266000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jpcafh\/article\/129\/35\/8110\/3648580\/Gas-Phase-Benzene-Methanol-Dimer-Configurations"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,8,23]]},"references-count":53,"journal-issue":{"issue":"35","published-online":{"date-parts":[[2025,8,23]]},"published-print":{"date-parts":[[2025,9,4]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jpca.5c03923","relation":{},"ISSN":["1089-5639","1520-5215"],"issn-type":[{"value":"1089-5639","type":"print"},{"value":"1520-5215","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,8,23]]}}}