{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,2]],"date-time":"2025-11-02T10:35:43Z","timestamp":1762079743323,"version":"build-2065373602"},"reference-count":86,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2020,5,7]],"date-time":"2020-05-07T00:00:00Z","timestamp":1588809600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100014440","name":"Ministerio de Ciencia, Innovaci\u00f3n y Universidades","doi-asserted-by":"publisher","award":["PGC2018-094644-B-C2"],"award-info":[{"award-number":["PGC2018-094644-B-C2"]}],"id":[{"id":"10.13039\/100014440","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100012818","name":"Comunidad de Madrid","doi-asserted-by":"publisher","award":["PS2018\/EMT-4329 AIRTEC-CM"],"award-info":[{"award-number":["PS2018\/EMT-4329 AIRTEC-CM"]}],"id":[{"id":"10.13039\/100012818","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Materials"],"abstract":"<jats:p>A theoretical study of the hydrogen bond (HB) and halogen bond (XB) complexes between 1-halo-closo-carboranes and hydrogen cyanide (NCH) as HB and XB probe has been carried out at the MP2 computational level. The energy results show that the HB complexes are more stable than the XBs for the same system, with the exception of the isoenergetic iodine derivatives. The analysis of the electron density with the quantum theory of atoms in molecules (QTAIM) shows the presence of a unique intermolecular bond critical point with the typical features of weak noncovalent interactions (small values of the electron density and positive Laplacian and total energy density). The natural energy decomposition analysis (NEDA) of the complexes shows that the HB and XB complexes are dominated by the charge-transfer and polarization terms, respectively. The work has been complemented with a search in the CSD database of analogous complexes and the comparison of the results, with those of the 1-halobenzene:NCH complexes showing smaller binding energies and larger intermolecular distances as compared to the 1-halo-closo-carboranes:NCH complexes.<\/jats:p>","DOI":"10.3390\/ma13092163","type":"journal-article","created":{"date-parts":[[2020,5,8]],"date-time":"2020-05-08T03:45:20Z","timestamp":1588909520000},"page":"2163","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Hydrogen vs. Halogen Bonds in 1-Halo-Closo-Carboranes"],"prefix":"10.3390","volume":"13","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6876-6211","authenticated-orcid":false,"given":"Ibon","family":"Alkorta","sequence":"first","affiliation":[{"name":"Instituto de Qu\u00edmica M\u00e9dica, CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jose","family":"Elguero","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica M\u00e9dica, CSIC, Juan de la Cierva, 3, E-28006 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Josep M.","family":"Oliva-Enrich","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica-F\u00edsica \u201cRocasolano\u201d, CSIC, Serrano, 119, E-28006 Madrid, Spain"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2020,5,7]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Alkorta, I., Elguero, J., and Frontera, A. (2020). Not Only Hydrogen Bonds: Other Noncovalent Interactions. Crystals, 10.","DOI":"10.3390\/cryst10030180"},{"key":"ref_2","unstructured":"Mulliken, R.S., and Person, W.B. (1969). Molecular Complexes: A Lecture and Reprint Volume, Wiley-Interscience."},{"key":"ref_3","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\u22c5\u22c5\u22c5XY of the Hydrogen Bond B\u22c5\u22c5\u22c5HX","volume":"38","author":"Legon","year":"1999","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"375","DOI":"10.1517\/17460441.2012.678829","article-title":"Halogen bonding for rational drug design and new drug discovery","volume":"7","author":"Lu","year":"2012","journal-title":"Expert Opin. Drug Dis."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1363","DOI":"10.1021\/jm3012068","article-title":"Principles and Applications of Halogen Bonding in Medicinal Chemistry and Chemical Biology","volume":"56","author":"Wilcken","year":"2013","journal-title":"J. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Mendez, L., Henriquez, G., Sirimulla, S., and Narayan, M. (2017). Looking Back, Looking Forward at Halogen Bonding in Drug Discovery. Molecules, 22.","DOI":"10.3390\/molecules22091397"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2686","DOI":"10.1021\/ar400103r","article-title":"The Halogen Bond in the Design of Functional Supramolecular Materials: Recent Advances","volume":"46","author":"Priimagi","year":"2013","journal-title":"Acc. Chem. Res."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3559","DOI":"10.1039\/C5PY00354G","article-title":"Halogen bonding in polymer science: From crystal engineering to functional supramolecular polymers and materials","volume":"6","author":"Berger","year":"2015","journal-title":"Polym. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1369","DOI":"10.1002\/chem.201802927","article-title":"The Halogen Bond: An Emerging Supramolecular Tool in the Design of Functional Mesomorphic Materials","volume":"25","author":"Wang","year":"2019","journal-title":"Chem. Eur. J."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Metrangolo, P., and Resnati, G. (2008). Halogen Bonding. Fundamentals and Applications, Springer.","DOI":"10.1007\/978-3-540-74330-9"},{"key":"ref_11","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_12","doi-asserted-by":"crossref","unstructured":"Yang, H., and Wong, M.W. (2020). Application of Halogen Bonding to Organocatalysis: A Theoretical Perspective. Molecules, 25.","DOI":"10.3390\/molecules25051045"},{"key":"ref_13","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_14","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_15","doi-asserted-by":"crossref","first-page":"7748","DOI":"10.1039\/c004189k","article-title":"Halogen bonding: An electrostatically-driven highly directional noncovalent interaction","volume":"12","author":"Politzer","year":"2010","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"11178","DOI":"10.1039\/c3cp00054k","article-title":"Halogen bonding and other \u03c3-hole interactions: A perspective","volume":"15","author":"Politzer","year":"2013","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2559","DOI":"10.1007\/s00894-013-1804-1","article-title":"Insights into the strength and nature of carbene\u22efhalogen bond interactions: A theoretical perspective","volume":"19","author":"Esrafili","year":"2013","journal-title":"J. Mol. Model."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"3024","DOI":"10.1080\/00268976.2014.926031","article-title":"Halogen bonds with N-heterocyclic carbenes as halogen acceptors: A partially covalent character","volume":"112","author":"Lv","year":"2014","journal-title":"Mol. Phys."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5745","DOI":"10.1021\/acs.jpca.6b05367","article-title":"B4H4 and B4(CH3)4 as Unique Electron Donors in Hydrogen-Bonded and Halogen-Bonded Complexes","volume":"120","author":"Alkorta","year":"2016","journal-title":"J. Phys. Chem. A"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1002\/qua.24533","article-title":"Some measures for mediating the strengths of halogen bonds with the B\u2013B bond in diborane(4) as an unconventional halogen acceptor","volume":"114","author":"Zhuo","year":"2014","journal-title":"Int. J. Quantum Chem"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1016\/j.jmgm.2018.06.017","article-title":"Dual function of the boron center of BH(CO)2\/BH(N2)2 in halogen- and triel-bonded complexes with hypervalent halogens","volume":"84","author":"Dong","year":"2018","journal-title":"J. Mol. Graph. Model."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"3112","DOI":"10.1002\/cphc.201600435","article-title":"Boron as an Electron-Pair Donor for B\u22c5\u22c5\u22c5Cl Halogen Bonds","volume":"17","author":"Alkorta","year":"2016","journal-title":"ChemPhysChem"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"373","DOI":"10.1039\/a606118d","article-title":"A pseudo-\u03c0 analogue of a Mulliken b\u03c0.a\u03c3 type complex: The rotational spectrum of cyclopropane\u2013chlorine monofluoride","volume":"93","author":"Holloway","year":"1997","journal-title":"J. Chem. Soc. Faraday Trans."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"32593","DOI":"10.1039\/C6CP06474D","article-title":"Unusual acid\u2013base properties of the P4 molecule in hydrogen-, halogen-, and pnicogen-bonded complexes","volume":"18","author":"Alkorta","year":"2016","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1891","DOI":"10.1039\/FT9959101891","article-title":"The b\u03c0.a\u03c3 complex C2H2\u22efCl2 characterised by rotational spectroscopy as an intermediate in a reactive mixture of ethyne and chlorine","volume":"91","author":"Bloemink","year":"1995","journal-title":"J. Chem. Soc. Faraday Trans."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"3021","DOI":"10.1021\/jp9628646","article-title":"Density Functional Studies of the b\u03c0.a\u03c3 Charge-Transfer Complex Formed between Ethyne and Chlorine Monofluoride","volume":"101","author":"Cruz","year":"1997","journal-title":"J. Phys. Chem. A"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s00214-009-0690-1","article-title":"Cooperativity in multiple unusual weak bonds","volume":"126","author":"Alkorta","year":"2010","journal-title":"Theor. Chem. Acc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2775","DOI":"10.1021\/cr500344e","article-title":"Cooperativity in Noncovalent Interactions","volume":"116","author":"Mahadevi","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1903","DOI":"10.1080\/00268976.2018.1559373","article-title":"The influence of halogen-bonding cooperativity on the hydrogen and lithium bonds: An ab initio study","volume":"117","author":"Esrafili","year":"2019","journal-title":"Mol. Phys."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"8506","DOI":"10.1039\/C8CP00353J","article-title":"Cooperativity between hydrogen- and halogen bonds: The case of selenourea","volume":"20","author":"Ciancaleoni","year":"2018","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"4401","DOI":"10.1039\/C7CE01035D","article-title":"Hydrogen- and halogen-bond cooperativity in determining the crystal packing of dihalogen charge-transfer adducts: A study case from heterocyclic pentatomic chalcogenone donors","volume":"19","author":"Montis","year":"2017","journal-title":"CrystEngComm"},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Novoa, J.J., and Ruiz L\u00f3pez, M.F. (2014). Cooperativity of hydrogen and halogen bond interactions. 8th Congress on Electronic Structure: Principles and Applications (ESPA 2012): A Conference Selection from Theoretical Chemistry Accounts, Springer.","DOI":"10.1007\/978-3-642-41272-1"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1641","DOI":"10.1080\/00268976.2011.582050","article-title":"Cooperativity between the hydrogen bonding and halogen bonding in F3CX\u2009\u22ef\u2009NCH(CNH)\u2009\u22ef\u2009NCH(CNH) complexes (X=Cl, Br)","volume":"109","author":"Solimannejad","year":"2011","journal-title":"Mol. Phys."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"4222","DOI":"10.1021\/jp503436f","article-title":"Characterizing Traditional and Chlorine-Shared Halogen Bonds in Complexes of Phosphine Derivatives with ClF and Cl2","volume":"118","author":"Alkorta","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"8461","DOI":"10.1021\/acs.jpca.6b08945","article-title":"Halogen Bonding with Phosphine: Evidence for Mulliken Inner Complexes and the Importance of Relaxation Energy","volume":"120","author":"Shaw","year":"2016","journal-title":"J. Phys. Chem. A"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"9552","DOI":"10.1021\/jp506663x","article-title":"Traditional and Ion-Pair Halogen-Bonded Complexes between Chlorine and Bromine Derivatives and a Nitrogen-Heterocyclic Carbene","volume":"118","author":"Jaque","year":"2014","journal-title":"J. Phys. Chem. A"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"12958","DOI":"10.1021\/jp110295n","article-title":"Do Traditional, Chlorine-shared, and Ion-pair Halogen Bonds Exist? An ab Initio Investigation of FCl: CNX Complexes","volume":"114","author":"Alkorta","year":"2010","journal-title":"J. Phys. Chem. A"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"19137","DOI":"10.1039\/C4CP03412K","article-title":"The halogen bond in thiirane\u22efClF: An example of a Mulliken inner complex","volume":"16","year":"2014","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1016\/0009-2614(95)01313-X","article-title":"Is the gas-phase complex of ammonia and chlorine monofluoride H3N\u2026ClF or [H3NCl]+\u2026F\u2212? Evidence from rotational spectroscopy","volume":"248","author":"Bloemink","year":"1996","journal-title":"Chem. Phys. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"600","DOI":"10.1021\/ja01157a151","article-title":"Structures of Complexes Formed by Halogen Molecules with Aromatic and with Oxygenated Solvents1","volume":"72","author":"Mulliken","year":"1950","journal-title":"J. Am. Chem. Soc."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3726","DOI":"10.1021\/ct500422t","article-title":"On The Nature of the Halogen Bond","volume":"10","author":"Wang","year":"2014","journal-title":"J. Chem. Theor. Comput."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"8719","DOI":"10.1002\/chem.201701116","article-title":"Halogen Bonds in Novel Polyhalogen Monoanions","volume":"23","author":"Wang","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"905","DOI":"10.1039\/C7CP06959F","article-title":"Characterizing the interplay of Pauli repulsion, electrostatics, dispersion and charge transfer in halogen bonding with energy decomposition analysis","volume":"20","author":"Thirman","year":"2018","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"7708","DOI":"10.1039\/c2cc33304j","article-title":"Unexpected trends in halogen-bond based noncovalent adducts","volume":"48","author":"Huber","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"232","DOI":"10.1021\/ct700216w","article-title":"Investigations into the Nature of Halogen Bonding Including Symmetry Adapted Perturbation Theory Analyses","volume":"4","author":"Riley","year":"2008","journal-title":"J. Chem. Theory Comput."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1021\/ct8004134","article-title":"Br\u22efO Complexes as Probes of Factors Affecting Halogen Bonding: Interactions of Bromobenzenes and Bromopyrimidines with Acetone","volume":"5","author":"Riley","year":"2009","journal-title":"J. Chem. Theory Comput."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"4651","DOI":"10.1007\/s00894-012-1428-x","article-title":"Halogen bond tunability II: The varying roles of electrostatic and dispersion contributions to attraction in halogen bonds","volume":"19","author":"Riley","year":"2013","journal-title":"J. Mol. Model."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"33031","DOI":"10.1039\/C6CP06613E","article-title":"The intrinsic strength of the halogen bond: Electrostatic and covalent contributions described by coupled cluster theory","volume":"18","author":"Oliveira","year":"2016","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_49","unstructured":"Grimes, R.N. (2016). Carboranes, Academic Press. [3rd ed.]."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1100","DOI":"10.1002\/cphc.200500648","article-title":"Interaction of Carboranes with Biomolecules: Formation of Dihydrogen Bonds","volume":"7","author":"Horinek","year":"2006","journal-title":"ChemPhysChem"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"19944","DOI":"10.1039\/C9CP03858B","article-title":"closo-Carboranes as dual CH\u22ef\u03c0 and BH\u22ef\u03c0 donors: Theoretical study and biological significance","volume":"21","author":"Frontera","year":"2019","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_52","unstructured":"Yan, H., Tu, D., Poater, J., and Sol\u00e0, M. (2020). nido-Cage\u22ef\u03c0 Bond: A Non-covalent Interaction between Boron Clusters and Aromatic Rings and Its Applications. Angew. Chem. Int. Ed."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"3373","DOI":"10.1002\/cphc.201600848","article-title":"Competition between Halogen, Hydrogen and Dihydrogen Bonding in Brominated Carboranes","volume":"17","author":"Holub","year":"2016","journal-title":"ChemPhysChem"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"6122","DOI":"10.1039\/D0CP00114G","article-title":"Halogen\u22efhalogen interactions in decahalo-closo-carboranes: CSD analysis and theoretical study","volume":"22","author":"Frontera","year":"2020","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1002\/ejic.201801094","article-title":"Trinuclear Gold\u2013Carborane Cluster as a Host Structure","volume":"2019","author":"Laguna","year":"2019","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Crespo, O., Gimeno, M.C., Laguna, A., Ospino, I., Aull\u00f3n, G., and Oliva, J.M. (2009). Organometallic gold complexes of carborane. Theoretical comparative analysis of ortho, meta, and para derivatives and luminescence studies. Dalton Trans., 3807\u20133813.","DOI":"10.1039\/b820803d"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2443","DOI":"10.1002\/cphc.201900687","article-title":"Tetravalent Oxygen and Sulphur Centres Mediated by Carborane Superacid: Theoretical Analysis","volume":"20","author":"Grabowski","year":"2019","journal-title":"ChemPhysChem"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1103\/PhysRev.46.618","article-title":"Note on an Approximation Treatment for Many-Electron Systems","volume":"46","author":"Plesset","year":"1934","journal-title":"Phys. Rev."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1007","DOI":"10.1063\/1.456153","article-title":"Gaussian-Basis Sets for Use in Correlated Molecular Calculations 1. The Atoms Boron through Neon and Hydrogen","volume":"90","author":"Dunning","year":"1989","journal-title":"J. Chem. Phys."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"283","DOI":"10.1007\/s00214-005-0681-9","article-title":"Systematically convergent basis sets for transition metals. II. Pseudopotential-based correlation consistent basis sets for the group 11 (Cu, Ag, Au) and 12 (Zn, Cd, Hg) elements","volume":"114","author":"Peterson","year":"2005","journal-title":"Theor. Chem. Acc."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1016\/S0009-2614(99)00179-7","article-title":"Basis-set convergence of the energy in molecular Hartree\u2013Fock calculations","volume":"302","author":"Halkier","year":"1999","journal-title":"Chem. Phys. Lett."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"9157","DOI":"10.1063\/1.479830","article-title":"Basis set convergence of the interaction energy of hydrogen-bonded complexes","volume":"111","author":"Halkier","year":"1999","journal-title":"J. Chem. Phys."},{"key":"ref_63","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. A.03, Gaussian Inc."},{"key":"ref_64","unstructured":"Werner, H.J., Knowles, P.J., Knizia, G., Manby, F.R., Sch\u00fctz, M., Celani, P., Gy\u00f6rffy, W., Kats, D., Korona, T., and Lindh, R. (MOLPRO, Version 2012.1, A Package of ab Initio Programs, 2012). MOLPRO, Version 2012.1, A Package of ab Initio Programs."},{"key":"ref_65","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":"J. Mol. Model."},{"key":"ref_66","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_67","doi-asserted-by":"crossref","first-page":"580","DOI":"10.1002\/jcc.22885","article-title":"Multiwfn: A multifunctional wavefunction analyzer","volume":"33","author":"Lu","year":"2012","journal-title":"J. Comput. Chem."},{"key":"ref_68","unstructured":"(2020, February 24). Jmol: An Open-Source Java Viewer for Chemical Structures in 3D. Available online: http:\/\/www.jmol.org\/."},{"key":"ref_69","doi-asserted-by":"crossref","unstructured":"Bader, R.F.W. (1990). Atoms in Molecules: A Quantum Theory, Clarendon Press.","DOI":"10.1093\/oso\/9780198551683.001.0001"},{"key":"ref_70","unstructured":"Popelier, P.L.A. (2000). Atoms in Molecules. An introduction, Prentice Hall."},{"key":"ref_71","first-page":"1259","article-title":"A description of the chemical bond in terms of local properties of electron density and energy","volume":"57","author":"Cremer","year":"1984","journal-title":"Croat. Chem. Acta"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"11154","DOI":"10.1021\/ja0017864","article-title":"Behavior of Ylides Containing N, O, and C Atoms as Hydrogen Bond Acceptors","volume":"122","author":"Rozas","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref_73","unstructured":"Keith, T.A. (2017). AIMAll, TK Gristmill Software. Version 17.11.14 B."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"6498","DOI":"10.1021\/ja100936w","article-title":"Revealing Noncovalent Interactions","volume":"132","author":"Johnson","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"625","DOI":"10.1021\/ct100641a","article-title":"NCIPLOT: A Program for Plotting Noncovalent Interaction Regions","volume":"7","author":"Johnson","year":"2011","journal-title":"J. Chem. Theor. Comput."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1016\/0263-7855(96)00018-5","article-title":"VMD: Visual molecular dynamics","volume":"14","author":"Humphrey","year":"1996","journal-title":"J. Mol. Graph."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"11936","DOI":"10.1021\/jp058209s","article-title":"Natural Energy Decomposition Analysis:\u2009 Extension to Density Functional Methods and Analysis of Cooperative Effects in Water Clusters","volume":"109","author":"Glendening","year":"2005","journal-title":"J. Phys. Chem. A"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"2473","DOI":"10.1021\/ja951834y","article-title":"Natural Energy Decomposition Analysis:\u2009 Explicit Evaluation of Electrostatic and Polarization Effects with Application to Aqueous Clusters of Alkali Metal Cations and Neutrals","volume":"118","author":"Glendening","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"899","DOI":"10.1021\/cr00088a005","article-title":"Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint","volume":"88","author":"Reed","year":"1988","journal-title":"Chem. Rev."},{"key":"ref_80","unstructured":"Glendening, E.D., Reed, A.E., Carpenter, J.E., Bohmann, J.A., Morales, C.M., Karafiloglou, P., Landis, C.R., and Weinhold, F. (2018). NBO 7.0, Theoretical Chemistry Institute, University of Wisconsin."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1107\/S0108768102003890","article-title":"The Cambridge Structural Database: A quarter of a million crystal structures and rising","volume":"58","author":"Allen","year":"2002","journal-title":"Acta Cryst. B"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"9925","DOI":"10.1021\/jp9824813","article-title":"Bifurcated Hydrogen Bonds:\u2009 Three-Centered Interactions","volume":"102","author":"Rozas","year":"1998","journal-title":"J. Phys. Chem. A"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1002\/poc.596","article-title":"An analysis of bifurcated H-bonds: Crystal and molecular structures of O, O-diphenyl 1-(3-phenylthioureido) pentanephosphonate and O,O-diphenyl 1-(3-phenylthioureido)butanephosphonate","volume":"16","author":"Grabowski","year":"2003","journal-title":"J. Phys. Org. Chem."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"2442","DOI":"10.1002\/chem.200901628","article-title":"Universal Features of the Electron Density Distribution in Hydrogen-Bonding Regions: A Comprehensive Study Involving H\u22efX (X = H, C, N, O, F, S, Cl, pi) Interactions","volume":"16","author":"Mata","year":"2010","journal-title":"Chem. Eur. J."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"7154","DOI":"10.1021\/jp073112m","article-title":"Theoretical Study of Complexes and Fluoride Cation Transfer between N2F+ and Electron Donors","volume":"111","author":"Alkorta","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"2543","DOI":"10.1080\/00268976.2011.621458","article-title":"Theoretical study of the HXYH dimers (X,\u2009Y = O, S, Se). Hydrogen bonding and chalcogen\u2013chalcogen interactions","volume":"109","author":"Alkorta","year":"2011","journal-title":"Mol. Phys."}],"container-title":["Materials"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1996-1944\/13\/9\/2163\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T09:26:30Z","timestamp":1760174790000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1996-1944\/13\/9\/2163"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,5,7]]},"references-count":86,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2020,5]]}},"alternative-id":["ma13092163"],"URL":"https:\/\/doi.org\/10.3390\/ma13092163","relation":{},"ISSN":["1996-1944"],"issn-type":[{"type":"electronic","value":"1996-1944"}],"subject":[],"published":{"date-parts":[[2020,5,7]]}}}