{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:57:22Z","timestamp":1787029042752,"version":"build-2736575974"},"reference-count":106,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2019,5,10]],"date-time":"2019-05-10T00:00:00Z","timestamp":1557446400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The intermolecular interaction in difluoromethane, dichloromethane, dibromomethane, and diiodomethane dimers has been investigated using high level quantum chemical methods. The potential energy curve of intermolecular interaction along the C\u22efC bond distance obtained using the coupled-cluster theory with singles, doubles, and perturbative triples excitations CCSD(T) were compared with values given by the same method, but applying the local (LCCSD(T)) and the explicitly correlated (CCSD(T)-F12) approximations. The accuracy of other theoretical methods\u2014Hartree\u2013Fock (HF), second order M\u00f8ller\u2013Plesset perturbation (MP2), and dispersion corrected DFT theory\u2014were also presented. In the case of MP2 level, the canonical and the local-correlation cases combined with the density-fitting technique (DF-LMP2)theories were considered, while for the dispersion-corrected DFT, the empirically-corrected BLYP-D and the M06-2Xexchange-correlation functionals were applied. In all cases, the aug-cc-pVTZ basis set was used, and the results were corrected for the basis set superposition error (BSSE) using the counterpoise method. For each molecular system, several dimer geometries were found, and their mutual orientations were compared with the nearest neighbor orientations obtained in recent neutron scattering studies. The nature of the intermolecular interaction energy was discussed.<\/jats:p>","DOI":"10.3390\/molecules24091810","type":"journal-article","created":{"date-parts":[[2019,5,13]],"date-time":"2019-05-13T03:57:07Z","timestamp":1557719827000},"page":"1810","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Intermolecular Interaction in Methylene Halide (CH2F2, CH2Cl2, CH2Br2 and CH2I2) Dimers"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5750-5788","authenticated-orcid":false,"given":"L\u00e1szl\u00f3","family":"Alm\u00e1sy","sequence":"first","affiliation":[{"name":"State Key Laboratory of Environment-friendly Energy Materials, Southwest University of Science and Technology, Mianyang 621010, China"},{"name":"Institute for Solid State Physics and Optics, Wigner Research Centre for Physics, Konkoly Thege \u00fat 29-33, 1121 Budapest, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5347-1514","authenticated-orcid":false,"given":"Attila","family":"Bende","sequence":"additional","affiliation":[{"name":"Molecular and Biomolecular Physics Department, National Institute for Research and Development of Isotopic and Molecular Technologies, Donat Street, No. 67-103, Ro-400293 Cluj-Napoca, Romania"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2019,5,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1220","DOI":"10.1039\/b906285h","article-title":"Robust hydrogen bonding synthon in one-dimensional and two-dimensional coordination polymers of pyridine-appended reverse amides and amides","volume":"11","author":"Rajput","year":"2009","journal-title":"CrystEngComm"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1416","DOI":"10.1039\/b820737b","article-title":"Molecular bricklaying II","volume":"11","author":"Verdan","year":"2009","journal-title":"CrystEngComm"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1080\/00018738200101398","article-title":"Organic conductors and superconductors","volume":"31","author":"Shulz","year":"1982","journal-title":"Adv. Phys."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"837","DOI":"10.1016\/0022-2836(91)90271-7","article-title":"\u03c0 \u2212 \u03c0 interactions: The geometry and energetics of phenylalanine-phenylalanine interactions in proteins","volume":"218","author":"Hunter","year":"1991","journal-title":"J. Mol. Biol."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Saenger, W. (1984). Principles of Nucleic Acid Structure, Springer.","DOI":"10.1007\/978-1-4612-5190-3"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1039\/B313660B","article-title":"Theoretical studies of hydrogen bonding","volume":"100","author":"Hobza","year":"2004","journal-title":"Annu. Rep. Prog. Chem. Sect. C Phys. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"3430","DOI":"10.1002\/anie.200705157","article-title":"Do special noncovalent \u03c0 \u2212 \u03c0 stacking interactions really exist?","volume":"47","author":"Grimme","year":"2008","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"114304","DOI":"10.1063\/1.2178795","article-title":"Estimated MP2 and CCSD(T) interaction energies of n-alkane dimers at the basis set limit: Comparison of the methods of Helgaker et al. and Feller","volume":"124","author":"Tsuzuki","year":"2006","journal-title":"J. Chem. Phys."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"6837","DOI":"10.1039\/b926355a","article-title":"Competition between hydrogen bond and halogen bond in complexes of formaldehyde with hypohalous acids","volume":"12","author":"Li","year":"2010","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/j.theochem.2010.03.020","article-title":"Comparison in the complexes of oxygen-containing \u03c3-electron donor with hydrogen halide and dihalogen molecules","volume":"950","author":"Zhang","year":"2010","journal-title":"J. Mol. Struct. Theochem."},{"key":"ref_11","first-page":"o604","article-title":"Halogen bonding in 1,2-dibromo-4,5-dimethoxybenzene and 1,2-diiodo-4,5-dimethoxybenzene","volume":"C64","author":"Cukiernik","year":"2008","journal-title":"Acta Cryst."},{"key":"ref_12","first-page":"o233","article-title":"Comparison of halogen bonding and van der Waals and \u03c0 \u2212 \u03c0 interactions in 4,5-dibromo-2-hexylphenol","volume":"C65","author":"Cukiernik","year":"2009","journal-title":"Acta Cryst."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"172","DOI":"10.1016\/j.jsb.2009.10.006","article-title":"Halogen\u2013water\u2013hydrogen bridges in biomolecules","volume":"169","author":"Zhou","year":"2010","journal-title":"J. Struct Biol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"4543","DOI":"10.1039\/b926326h","article-title":"Nonbonding interactions of organic halogens in biological systems: Implications for drug discovery and biomolecular design","volume":"12","author":"Lu","year":"2010","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1016\/j.molstruc.2005.12.059","article-title":"Theoretical study of the blue-shifting hydrogen bonds between CH2X2 and CHX3 (X = F, Cl, Br) and hydrogen peroxide","volume":"792\u2013793","author":"Nguyen","year":"2006","journal-title":"J. Mol. Struct."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1007\/s00894-006-0130-2","article-title":"Halogen bonding: The \u03c3-hole","volume":"13","author":"Clark","year":"2007","journal-title":"J. Mol. Model."},{"key":"ref_17","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_18","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1002\/jcc.21302","article-title":"Properties of halogen atoms for representing intermolecular electrostatic interactions related to halogen bonding and their substituent effects","volume":"31","author":"Torii","year":"2010","journal-title":"J. Comput. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1002\/cphc.201200799","article-title":"Halogen Bonding: An Interim Discussion","volume":"14","author":"Politzer","year":"2013","journal-title":"ChemPhysChem"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"255","DOI":"10.1016\/S0022-2860(02)00096-0","article-title":"A molecular-beam Fourier transform microwave study of difluoromethane dimer","volume":"612","author":"Blanco","year":"2002","journal-title":"J. Mol. Struct."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1802","DOI":"10.1021\/jp045337s","article-title":"Dissociative Photoionization and Thermochemistry of Dihalomethane Compounds Studied by Threshold Photoelectron Photoion Coincidence Spectroscopy","volume":"109","author":"Lago","year":"2005","journal-title":"J. Phys. Chem. A"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"5908","DOI":"10.1021\/jp711894k","article-title":"Dimethylselenide as a Probe for Reactions of Halogenated Alkoxyl Radicals in Aqueous Solution. Degradation of Dichloro- and Dibromomethane","volume":"112","author":"Makogon","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"11548","DOI":"10.1021\/jp4077323","article-title":"Experimental Characterization of C\u2013X\u22efY\u2013C (X = Br, I; Y = F, Cl) Halogen\u2013Halogen Bonds","volume":"117","author":"Hauchecorne","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Shimizu, K., and da Silva, J.F. (2018). Halogen and Hydrogen Bonding Interplay in the Crystal Packing of Halometallocenes. Molecules, 23.","DOI":"10.3390\/molecules23112959"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"7118","DOI":"10.1021\/cr500674c","article-title":"Halogen Bonding in Supramolecular Chemistry","volume":"115","author":"Gilday","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"13308","DOI":"10.1021\/acs.chemrev.5b00308","article-title":"Structure of Neat Liquids Consisting of (Perfect and Nearly) Tetrahedral Molecules","volume":"115","author":"Pothoczki","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_27","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_28","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_29","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_30","doi-asserted-by":"crossref","first-page":"2686","DOI":"10.1002\/(SICI)1521-3773(19990917)38:18<2686::AID-ANIE2686>3.0.CO;2-6","article-title":"Prereactive Complexes of Dihalogens XY with Lewis Bases B in the Gas Phase: A Systematic Case for the Halogen Analogue B\u22efXY of the Hydrogen Bond B\u22efHX","volume":"38","author":"Legon","year":"1999","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s00214-003-0448-0","article-title":"The intermolecular interaction in the charge-transfer complexes between amines and halogens","volume":"110","author":"Karpfen","year":"2003","journal-title":"Theor. Chem. Acc."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"449","DOI":"10.1002\/hc.20264","article-title":"Charge-Transfer Character of Halogen Bonding: Molecular Structures and Electronic Spectroscopy of Carbon Tetrabromide and Bromoform Complexes with Organic \u03c3- and \u03c0-Donors","volume":"17","author":"Rosokha","year":"2006","journal-title":"Heteroatom Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2319","DOI":"10.1021\/jp0660684","article-title":"The Nature of Halogen\u22efHalide Synthons: Theoretical and Crystallographic Studies","volume":"111","author":"Awwadi","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"4114","DOI":"10.1021\/jp710992h","article-title":"Origin of the X-Hal (Hal = Cl, Br) Bond-Length Change in the Halogen-Bonded Complexes","volume":"112","author":"Wang","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.molliq.2004.10.006","article-title":"Atomic quadrupolar effect in intermolecular electrostatic interactions of chloroalkanes: the cases of chloroform and dichloromethane","volume":"119","author":"Torii","year":"2005","journal-title":"J. Mol. Liq."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"5","DOI":"10.1107\/S205225251303491X","article-title":"Type II halogen\u22efhalogen contacts are halogen bonds","volume":"1","author":"Metrangolo","year":"2014","journal-title":"IUCrJ"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1021\/ja036994l","article-title":"Halogen bonding: A new interaction for liquid crystal formation","volume":"126","author":"Nguyen","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1007\/s00214-010-0830-7","article-title":"Theoretical evaluation of the nature and strength of the F\u22efF intermolecular interactions present in fluorinated hydrocarbons","volume":"128","author":"Osuna","year":"2011","journal-title":"Theor. Chem. Acc."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4910","DOI":"10.1021\/ja00090a041","article-title":"The Nature of -Cl\u22efCl- Intermolecular Interactions","volume":"116","author":"Price","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"3411","DOI":"10.1002\/chem.200305584","article-title":"Weak Hydrogen Bridges: A Systematic Theoretical Study on the Nature and Strength of C\u2013H\u22efF\u2013C Interactions","volume":"10","author":"Haufe","year":"2004","journal-title":"Chem. Eur. J."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"12322","DOI":"10.1039\/C6CC06842A","article-title":"Supramolecular anion recognition by \u03b2-HCH","volume":"52","author":"Rednic","year":"2016","journal-title":"Chem. Commun."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"20691","DOI":"10.1039\/C7CP02911J","article-title":"The nature of intermolecular interactions in pyridinium\u2013anion\u2013\u03b2-hexachlorocyclohexane molecular crystals","volume":"19","author":"Grosu","year":"2017","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"14931","DOI":"10.1002\/chem.201703459","article-title":"Anti-Electrostatic CH\u2013Ion Bonding in Decorated Graphanes","volume":"23","author":"Marek","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Varadwaj, A., Marques, H.M., and Varadwaj, P.R. (2019). Is the Fluorine in Molecules Dispersive? Is Molecular Electrostatic Potential a Valid Property to Explore Fluorine-Centered Non-Covalent Interactions?. Molecules, 24.","DOI":"10.3390\/molecules24030379"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2501","DOI":"10.1021\/jp973374w","article-title":"Anti-Hydrogen Bond in the Benzene Dimer and Other Carbon Proton Donor Complexes","volume":"102","author":"Hobza","year":"1998","journal-title":"J. Phys. Chem. A"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"6394","DOI":"10.1021\/jp990258f","article-title":"Hydrogen Bond versus Anti-Hydrogen Bond: A Comparative Analysis","volume":"103","author":"Cubero","year":"1999","journal-title":"J. Phys. Chem. A"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"12290","DOI":"10.1021\/ja010915t","article-title":"The Nature of Improper, Blue-Shifting Hydrogen Bonding Verified Experimentally","volume":"123","author":"Herrebout","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"325","DOI":"10.1007\/s00214-002-0367-5","article-title":"Improper, blue-shifting hydrogen bond","volume":"108","author":"Hobza","year":"2002","journal-title":"Theor. Chem. Acc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2527","DOI":"10.1021\/jp0365108","article-title":"CH\u22efF Hydrogen Bonds. Dimers of Fluoromethanes","volume":"108","author":"Kryachko","year":"2004","journal-title":"J. Phys. Chem. A"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"87","DOI":"10.1016\/j.theochem.2004.07.021","article-title":"The characterization of stationary points in the potential energy surface of difluoromethane dimer","volume":"684","author":"Ebrahimi","year":"2004","journal-title":"J. Mol. Struct. (THEOCHEM)"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"511","DOI":"10.1002\/1439-7641(20020617)3:6<511::AID-CPHC511>3.0.CO;2-Y","article-title":"Study of the Nature of Improper Blue-Shifting Hydrogen Bonding and Standard Hydrogen Bonding in the X3CH\u22efOH2 and XH\u22efOH2 Complexes (X = F, Cl, Br, I): A Correlated Ab Initio Study","volume":"3","author":"Zierkiewicz","year":"2002","journal-title":"ChemPhysChem"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"151","DOI":"10.1016\/0009-2614(83)80703-9","article-title":"Localizability of dynamic electron correlation","volume":"100","author":"Pulay","year":"1983","journal-title":"Chem. Phys. Lett."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1146\/annurev.pc.44.100193.001241","article-title":"Local treatment of electron correlation","volume":"44","author":"Pulay","year":"1993","journal-title":"Annu. Rev. Phys. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"6286","DOI":"10.1063\/1.471289","article-title":"Local treatment of electron correlation in coupled cluster theory","volume":"104","author":"Hampel","year":"1996","journal-title":"J. Chem. Phys."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"9443","DOI":"10.1063\/1.1321295","article-title":"Low-order scaling local correlation methods II: Splitting the Coulomb operator in linear scaling local second-order M\u00f8ller\u2013Plesset perturbation theory","volume":"113","author":"Hetzer","year":"2000","journal-title":"J. Chem. Phys."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"9986","DOI":"10.1063\/1.1323265","article-title":"Low-order scaling local electron correlation methods. III. Linear scaling local perturbative triples correction (T)","volume":"113","year":"2000","journal-title":"J. Chem. Phys."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"661","DOI":"10.1063\/1.1330207","article-title":"Low-order scaling local electron correlation methods. IV. Linear scaling local coupled-cluster (LCCSD)","volume":"114","author":"Werner","year":"2001","journal-title":"J. Chem. Phys."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"514","DOI":"10.1016\/0009-2614(93)89151-7","article-title":"Integral approximations for LCAO-SCF calculations","volume":"213","author":"Vahtras","year":"1993","journal-title":"Chem. Phys. Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"4072","DOI":"10.1039\/b608623c","article-title":"Calculation of intermolecular interactions in the benzene dimer using coupled-cluster and local electron correlation methods","volume":"8","author":"Hill","year":"2006","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"9095","DOI":"10.1063\/1.1569242","article-title":"Improved second-order M\u00f8ller\u2013Plesset perturbation theory by separate scaling of parallel- and antiparallel-spin pair correlation energies","volume":"118","author":"Grimme","year":"2003","journal-title":"J. Chem. Phys."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"80","DOI":"10.1021\/ct6002737","article-title":"Spin-Component Scaling Methods for Weak and Stacking Interactions","volume":"3","author":"Hill","year":"2007","journal-title":"J. Chem. Theory Comput."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"1985","DOI":"10.1039\/B600027D","article-title":"Benchmark database of accurate (MP2 and CCSD(T) complete basis set limit) interaction energies of small model complexes, DNA base pairs, and amino acid pairs","volume":"8","author":"Hobza","year":"2006","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_63","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_64","doi-asserted-by":"crossref","first-page":"445","DOI":"10.1007\/BF00527669","article-title":"r12-Dependent terms in the wave function as closed sums of partial wave amplitudes for large l","volume":"68","author":"Kutzelnigg","year":"1985","journal-title":"Theor. Chim. Acta"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"427","DOI":"10.1080\/01442350600799921","article-title":"R12 methods in explicitly correlated molecular electronic structure theory","volume":"25","author":"Klopper","year":"2006","journal-title":"Int. Rev. Phys. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"174103","DOI":"10.1063\/1.2907741","article-title":"Explicitly correlated coupled cluster F12 theory with single and double excitations","volume":"128","author":"Noga","year":"2008","journal-title":"J. Chem. Phys."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"221106","DOI":"10.1063\/1.2817618","article-title":"A simple and efficient CCSD(T)-F12 approximation","volume":"127","author":"Adler","year":"2007","journal-title":"J. Chem. Phys."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"4479","DOI":"10.1063\/1.1780891","article-title":"An explicitly correlated second order M\u00f8ller\u2013Plesset theory using a frozen Gaussian geminal","volume":"121","author":"May","year":"2004","journal-title":"J. Chem. Phys."},{"key":"ref_69","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_70","doi-asserted-by":"crossref","first-page":"202","DOI":"10.1016\/j.chemphys.2008.10.016","article-title":"Weak intermolecular bonding in N,N\u2019-dimethylethyleneurea dimers and N,N\u2019-dimethylethyleneurea\u2013water systems: The role of the dispersion effects in intermolecular interaction","volume":"354","author":"Bende","year":"2008","journal-title":"Chem. Phys."},{"key":"ref_71","unstructured":"Werner, H.-J., Knowles, P.J., Lindh, R., Manby, F.R., Sch\u00fctz, M., Celani, P., Korona, T., Mitrushenkov, A., Rauhut, G., and Adler, T.B. (2019, May 09). MOLPRO, Version 2010.1, a Package of ab Initio Programs. Available online: http:\/\/www.molpro.net."},{"key":"ref_72","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_73","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_74","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_75","doi-asserted-by":"crossref","first-page":"7667","DOI":"10.1063\/1.478678","article-title":"Gaussian basis sets for use in correlated molecular calculations. IX. The atoms gallium through krypton","volume":"110","author":"Wilson","year":"1999","journal-title":"J. Chem. Phys."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"13877","DOI":"10.1021\/jp065887l","article-title":"On the Spectroscopic and Thermochemical Properties of ClO, BrO, IO, and Their Anions","volume":"110","author":"Peterson","year":"2006","journal-title":"J. Phys. Chem. A"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"4916","DOI":"10.1063\/1.456588","article-title":"A fast intrinsic localization procedure applicable for ab initio and semiempirical linear combination of atomic orbital wave functions","volume":"90","author":"Pipek","year":"1989","journal-title":"J. Chem. Phys."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"5997","DOI":"10.1021\/jp981168y","article-title":"Local Treatment of Electron Correlation in Molecular Clusters: Structures and Stabilities of (H2O)n, n = 2\u20134","volume":"102","author":"Rauhut","year":"1998","journal-title":"J. Phys. Chem. A"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1007\/s00214-007-0310-x","article-title":"The M06 Suite of Density Functionals for Main Group Thermochemistry, Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06 Functionals and Twelve Other Functionals","volume":"120","author":"Zhao","year":"2008","journal-title":"Theo. Chem. Acc."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1463","DOI":"10.1002\/jcc.20078","article-title":"Accurate description of van der Waals complexes by density functional theory including empirical corrections","volume":"25","author":"Grimme","year":"2004","journal-title":"J. Comput. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1787","DOI":"10.1002\/jcc.20495","article-title":"Semiempirical GGA-type density functional constructed with a long-range dispersion correction","volume":"27","author":"Grimme","year":"2006","journal-title":"J. Comput. Chem."},{"key":"ref_82","unstructured":"Bylaska, E.J., de Jong, W.A., Govind, N., Kowalski, K., Straatsma, T.P., Valiev, M., Wang, D., Apra, E., Windus, T.L., and Hammond, J. (2009). NWChem, A Computational Chemistry Package for Parallel Computers, Version 6.1."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"5201","DOI":"10.1021\/ct400818v","article-title":"On the Reliability of Pure and Hybrid DFT Methods for the Evaluation of Halogen, Chalcogen, and Pnicogen Bonds Involving Anionic and Neutral Electron Donors","volume":"9","author":"Alkorta","year":"2013","journal-title":"J. Chem. Theory Comput."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"5010","DOI":"10.1039\/B310529F","article-title":"The helium dimer potential from a combined density functional theory and symmetry-adapted perturbation theory approach using an exact exchange\u2013correlation potential","volume":"5","author":"Jansen","year":"2003","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"174","DOI":"10.1002\/jcc.21600","article-title":"Gabedit\u2014A graphical user interface for computational chemistry softwares","volume":"32","author":"Allouche","year":"2011","journal-title":"J. Comput. Chem."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1016\/j.molliq.2010.11.007","article-title":"Ab initio structures of interacting methylene chloride molecules with comparison to the liquid phase","volume":"158","author":"Bende","year":"2011","journal-title":"J. Mol. Liq."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"12479","DOI":"10.1021\/jp105012g","article-title":"Molecular Modeling of Phenothiazine Derivatives: Self-Assembling Properties","volume":"114","author":"Bende","year":"2010","journal-title":"J. Phys. Chem. A"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"17742","DOI":"10.1039\/c3cp52768a","article-title":"The relative roles of electrostatics and dispersion in the stabilization of halogen bonds","volume":"15","author":"Riley","year":"2013","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"7005","DOI":"10.1021\/ja401420w","article-title":"Are Halogen Bonded Structures Electrostatically Driven?","volume":"135","author":"Stone","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"858","DOI":"10.1039\/C4CP03376K","article-title":"On the directionality and non-linearity of halogen and hydrogen bonds","volume":"17","author":"Hill","year":"2015","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1016\/j.molliq.2010.01.011","article-title":"Partial radial distribution functions of methylene halide molecular liquids","volume":"153","author":"Pothoczki","year":"2010","journal-title":"J. Mol. Liq."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"164511","DOI":"10.1063\/1.3418444","article-title":"Extended orientational correlation study for molecular liquids containing distorted tetrahedral molecules: Application to methylene halides","volume":"132","author":"Pothoczki","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"164506","DOI":"10.1063\/1.2720840","article-title":"Quantitative characterization of orientational order in liquid carbon tetrachloride","volume":"126","author":"Rey","year":"2007","journal-title":"J. Chem. Phys."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"2924","DOI":"10.1002\/(SICI)1521-3773(19991004)38:19<2924::AID-ANIE2924>3.0.CO;2-N","article-title":"The C-F\u22efH-C \u201canti-hydrogen bond\u201d in the gas phase: Microwave structure of the difluoromethane dimer","volume":"38","author":"Caminati","year":"1999","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1016\/j.jms.2019.02.002","article-title":"Conformational landscape of the weakly bound difluoromethane-1,1-difluoroethane dimer explored by rotational spectroscopy and quantum chemical calculations","volume":"357","author":"Lu","year":"2019","journal-title":"J. Mol. Spectr."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"2700","DOI":"10.1021\/ja068599b","article-title":"Shapes and Noncovalent Interactions of Oligomers: The Rotational Spectrum of the Difluoromethane Trimer","volume":"129","author":"Blanco","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_97","first-page":"171","article-title":"Oligomers based on weak hydrogen bond networks: A rotational study of the tetramer of difluoromethane","volume":"50","author":"Feng","year":"2014","journal-title":"ChemComm"},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"2204","DOI":"10.1021\/ct500148g","article-title":"Computational Screening of Weak Hydrogen Bond Networks: Predicting Stable Structures for Difluoromethane Oligomers","volume":"10","author":"Prampolini","year":"2014","journal-title":"J. Chem. Theor. Comp."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"014202","DOI":"10.1103\/PhysRevB.85.014202","article-title":"Role of steric and electrostatic effects in the short-range order of quasitetrahedral molecular liquids","volume":"85","author":"Pothoczki","year":"2012","journal-title":"Phys. Rev. B"},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/j.molliq.2017.10.023","article-title":"On the local intermolecular ordering and dynamics of liquid chloroform","volume":"248","author":"Karnes","year":"2017","journal-title":"J. Mol. Liq."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"164507","DOI":"10.1063\/1.2721559","article-title":"Structure of liquid nitromethane: Comparison of simulation and diffraction studies","volume":"126","author":"Megyes","year":"2007","journal-title":"J. Chem. Phys."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/0009-2614(96)01049-4","article-title":"Evidence of dimer formation in neat liquid 1,3,5-trifluorobenzene","volume":"262","author":"Cabaco","year":"1996","journal-title":"Chem. Phys. Lett."},{"key":"ref_103","first-page":"595","article-title":"In situ high-pressure crystallization and compression of halogen contacts in dichloromethane","volume":"B61","author":"Dziubek","year":"2005","journal-title":"Acta Cryst."},{"key":"ref_104","first-page":"1090","article-title":"Molecular interactions in crystalline dibromomethane and diiodomethane, and the stabilities of their high-pressure and low-temperature phases","volume":"B62","author":"Dziubek","year":"2006","journal-title":"Acta Cryst."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"024506","DOI":"10.1063\/1.3293129","article-title":"Molecular dynamics simulation of liquid carbon tetrachloride using ab initio force field","volume":"132","author":"Li","year":"2010","journal-title":"J. Chem. Phys."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"194501","DOI":"10.1063\/1.4829760","article-title":"Liquid chloroform structure from computer simulation with a full ab initio intermolecular interaction potential","volume":"139","author":"Yin","year":"2013","journal-title":"J. Chem. Phys."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/9\/1810\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T12:50:47Z","timestamp":1760187047000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/24\/9\/1810"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,5,10]]},"references-count":106,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2019,5]]}},"alternative-id":["molecules24091810"],"URL":"https:\/\/doi.org\/10.3390\/molecules24091810","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,5,10]]}}}