{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,30]],"date-time":"2026-01-30T06:56:20Z","timestamp":1769756180617,"version":"3.49.0"},"reference-count":85,"publisher":"MDPI AG","issue":"23","license":[{"start":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T00:00:00Z","timestamp":1638316800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["21-13-00345"],"award-info":[{"award-number":["21-13-00345"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A simple and efficient method was developed for the one-pot synthesis of 3-aryl derivatives of ortho-carborane with sensitive functional groups using 3-iodo-ortho-carborane and aryl zinc bromides that were generated in situ. A series of 3-aryl-ortho-carboranes, including those containing nitrile and ester groups, 3-RC6H4-1,2-C2B10H11 (R = p-Me, p-NMe2, p-OCH2OMe, p-OMe, o-CN, p-CN, o-COOEt, m-COOEt, p-COOEt) was synthesized using this approach. The solid-state structures of 3-RC6H4-1,2-C2B10H11 (R = p-OMe, o-CN, and p-CN) were determined by single crystal X-ray diffraction. The intramolecular hydrogen bonding involving the ortho-substituents of the aryl ring and the CH and BH groups of carborane was discussed.<\/jats:p>","DOI":"10.3390\/molecules26237297","type":"journal-article","created":{"date-parts":[[2021,12,1]],"date-time":"2021-12-01T05:02:36Z","timestamp":1638334956000},"page":"7297","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Synthesis of 3-Aryl-ortho-carboranes with Sensitive Functional Groups"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-6386-7301","authenticated-orcid":false,"given":"Sergey A.","family":"Anufriev","sequence":"first","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Akim V.","family":"Shmal\u2019ko","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Kyrill Yu.","family":"Suponitsky","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5442-367X","authenticated-orcid":false,"given":"Igor B.","family":"Sivaev","sequence":"additional","affiliation":[{"name":"A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,12,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1016\/j.ica.2010.08.007","article-title":"Porosity tuning of carborane-based metal\u2013organic frameworks (MOFs) via coordination chemistry and ligand design","volume":"364","author":"Spokoyny","year":"2010","journal-title":"Inorg. Chim. Acta"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3539","DOI":"10.1021\/cm4020942","article-title":"Carborane-based metal\u2013organic framework with high methane and hydrogen storage capacities","volume":"25","author":"Kennedy","year":"2013","journal-title":"Chem. Mater."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1606","DOI":"10.1007\/s10118-015-1712-1","article-title":"Synthesis and characterization of carborane bisphenol resol phenolic resins with ultrahigh char yield","volume":"33","author":"Qi","year":"2015","journal-title":"Chin. J. Polym. Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"e1800484","DOI":"10.1002\/marc.201800484","article-title":"High Tg and thermo-oxidatively stable thermosetting polyimides derived from a carborane-containing diamine","volume":"39","author":"Wu","year":"2018","journal-title":"Macromol. Rapid Commun."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"109143","DOI":"10.1016\/j.polymdegradstab.2020.109143","article-title":"Study on thermal degradation mechanism of heat-resistant epoxy resin modified with carboranes","volume":"176","author":"Cui","year":"2020","journal-title":"Polym. Degrad. Stab."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1888","DOI":"10.1002\/chem.201503456","article-title":"Carboranes as a tool to tune phosphorescence","volume":"22","author":"Li","year":"2015","journal-title":"Chem. A Eur. J."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1070","DOI":"10.1039\/C5CC08213G","article-title":"Boron clusters in luminescent materials","volume":"52","author":"Mukherjee","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"9925","DOI":"10.1002\/ange.201916666","article-title":"Recent progress in the development of solid-state luminescent o-carboranes with stimuli responsivity","volume":"132","author":"Ochi","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Lee, S.H., Lee, J.H., Mun, M.S., Yi, S., Yoo, E., Hwang, H., and Lee, K.M. (2021). Influence of electronic environment on the radiative efficiency of 9-phenyl-9H-carbazole-based ortho-carboranyl luminophores. Molecules, 26.","DOI":"10.3390\/molecules26061763"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"8411","DOI":"10.1039\/D1SC00791B","article-title":"Strategic molecular design of closo-ortho-carboranyl luminophores to manifest thermally activated delayed fluorescence","volume":"12","author":"You","year":"2021","journal-title":"Chem. Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"8029","DOI":"10.1039\/D1DT00233C","article-title":"A \u201cflexible\u201d carborane-cored luminogen: Variable emission behaviours in aggregates","volume":"50","author":"Li","year":"2021","journal-title":"Dalton Trans."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3207","DOI":"10.1039\/D0DT04038J","article-title":"Impact of deboronation on the electronic characteristics of closo-o-carborane: Intriguing photophysical changes in triazole-appended carboranyl luminophores","volume":"50","author":"Kim","year":"2021","journal-title":"Dalton Trans."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2389","DOI":"10.1016\/S0960-894X(01)00438-3","article-title":"Utility of boron clusters for drug design. Hansch\u2013Fujita hydrophobic parameters \u03c0 of dicarba-closo-dodecaboranyl groups","volume":"11","author":"Yamamoto","year":"2001","journal-title":"Bioorganic Med. Chem. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"5701","DOI":"10.1021\/cr2000866","article-title":"Boron in drug discovery: Carboranes as unique pharmacophores in biologically active compounds","volume":"111","author":"Issa","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"7035","DOI":"10.1021\/cr200038x","article-title":"Carbaboranes as pharmacophores: Properties, synthesis, and application strategies","volume":"111","author":"Scholz","year":"2011","journal-title":"Chem. Rev."},{"key":"ref_16","first-page":"3","article-title":"Carboranes as hydrophobic pharmacophores: Applications for design of nuclear receptor ligands","volume":"Volume 1","year":"2018","journal-title":"Boron-Based Compounds: Potential and Emerging Applications in Medicine"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3497","DOI":"10.1039\/C9CS00197B","article-title":"New keys for old locks: Carborane-containing drugs as platforms for mechanism-based therapies","volume":"48","author":"Stockmann","year":"2019","journal-title":"Chem. Soc. Rev."},{"key":"ref_18","unstructured":"Grimes, R.N. (2016). Carboranes, Academic Press. [3rd ed.]."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1089","DOI":"10.1021\/ic50010a002","article-title":"A new series of organoboranes. I. Carboranes from the reaction of decaborane with acetylenic compounds","volume":"2","author":"Heying","year":"1963","journal-title":"Inorg. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"8569","DOI":"10.1021\/ic0509736","article-title":"1,2-Dicarba-closo-dodecaboran-1-yl naphthalene derivatives","volume":"44","author":"Ohta","year":"2005","journal-title":"Inorg. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"5084","DOI":"10.1002\/anie.201500129","article-title":"o-Carborane-based anthracene: A variety of emission behaviors","volume":"54","author":"Naito","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Kim, S., So, H., Lee, J.H., Hwang, H., Kwon, H., Park, M.H., and Lee, K.M. (2019). Photophysical properties of spirobifluorene-based o-carboranyl compounds altered by structurally rotating the carborane cages. Molecules, 24.","DOI":"10.3390\/molecules24224135"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2228","DOI":"10.1002\/ajoc.201900537","article-title":"Tuning of sensitivity in thermochromic luminescence by regulating molecular rotation based on triphenylamine-substituted o-carboranes","volume":"8","author":"Nishino","year":"2019","journal-title":"Asian J. Org. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2949","DOI":"10.1039\/D0QI00563K","article-title":"Insights into the effects of substitution position on the photophysics of mono-o-carborane-substituted pyrenes","volume":"7","author":"Kim","year":"2020","journal-title":"Inorg. Chem. Front."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"e93","DOI":"10.1002\/agt2.93","article-title":"Rational design for thermochromic luminescence in amorphous polystyrene films with bis-o-carborane-substituted enhanced conjugated molecule having aggregation-induced luminochromism","volume":"2","author":"Wada","year":"2021","journal-title":"Aggregate"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1016\/0022-328X(93)83337-U","article-title":"C-arylation and C-heteroarylation of icosahedral carboranes via their copper(I) derivatives","volume":"462","author":"Coult","year":"1993","journal-title":"J. Organomet. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1694","DOI":"10.1021\/ma971186y","article-title":"A carborane-based analogue of poly(p-phenylene)","volume":"31","author":"Colquhoun","year":"1998","journal-title":"Macromolecules"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"264","DOI":"10.1016\/j.ejmech.2014.07.034","article-title":"Design and synthesis of nonsteroidal progesterone receptor antagonists based on C,C\u2032-diphenylcarborane scaffold as a hydrophobic pharmacophore","volume":"84","author":"Fujii","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1002\/ange.201609656","article-title":"Solid-state emission of the anthracene-o-carborane dyad from the twisted-intramolecular charge transfer in the crystalline state","volume":"129","author":"Naito","year":"2016","journal-title":"Angew. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2000312","DOI":"10.1002\/aelm.202000312","article-title":"Correlating the structural and photophysical properties of ortho-, meta-, and para-carboranyl\u2013anthracene dyads","volume":"6","author":"Marsh","year":"2020","journal-title":"Adv. Electron. Mater."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"7662","DOI":"10.1002\/anie.201502502","article-title":"Nickel-catalyzed cross-coupling reactions of o-carboranyl with aryl iodides: Facile synthesis of 1-aryl-o-carboranes and 1,2-diaryl-o-carboranes","volume":"54","author":"Tang","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"5270","DOI":"10.1039\/C8SC00833G","article-title":"Mechanically triggered reversible stepwise tricolor switching and thermochromism of anthracene-o-carborane dyad","volume":"9","author":"Wu","year":"2018","journal-title":"Chem. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"257","DOI":"10.1039\/C9QM00621D","article-title":"Aggregation-induced emission characteristics of o-carborane-functionalized fluorene and its heteroanalogs: The influence of heteroatoms on photoluminescence","volume":"4","author":"Wu","year":"2019","journal-title":"Mater. Chem. Front."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1016\/S0022-328X(00)83405-1","article-title":"Synthesis of B-organo-substituted 1,2-, 1,7-, and 1,12-dicarbaclosododecarboranes(12)","volume":"226","author":"Zakharkin","year":"1982","journal-title":"J. Organomet. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2095","DOI":"10.1021\/ic00112a023","article-title":"Facile electrophilic iodination of icosahedral carboranes. Synthesis of carborane derivatives with boron-carbon bonds via the palladium-catalyzed reaction of diiodocarboranes with Grignard reagents","volume":"34","author":"Zheng","year":"1995","journal-title":"Inorg. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3491","DOI":"10.1021\/ic00117a018","article-title":"Iodination reactions of icosahedral para-carborane and the synthesis of carborane derivatives with boron-carbon bonds","volume":"34","author":"Jiang","year":"1995","journal-title":"Inorg. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","unstructured":"Lee, H., Knobler, C.B., and Hawthorne, M.F. (2000). Supramolecular self-assembly directed by carborane C\u2013H\u2025F interactions. Chem. Commun., 2485\u20132486.","DOI":"10.1039\/b007353i"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1301","DOI":"10.1039\/b108721e","article-title":"Model compounds and monomers for phenylene ether carboranylene ketone (PECK) polymer synthesis: Preparation and characterization of boron-arylated ortho-carboranes bearing carboxyphenyl, phenoxyphenyl or benzoylphenyl substituents","volume":"12","author":"Fox","year":"2002","journal-title":"J. Mater. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2732","DOI":"10.1002\/chem.200304803","article-title":"The synthesis of carboracycles derived from B,B\u2032-bis(aryl) derivatives of icosahedral ortho-carborane","volume":"9","author":"Bayer","year":"2003","journal-title":"Chem. A Eur. J."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"5339","DOI":"10.1002\/anie.201002181","article-title":"Electronic tuning of nickel-based bis(dicarbollide) redox shuttles in dye-sensitized solar cells","volume":"49","author":"Spokoyny","year":"2010","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"712","DOI":"10.1007\/s11172-015-0924-4","article-title":"Synthesis of 9,9\u2032,12,12\u2032-substituted cobalt bis(dicarbollide) derivatives","volume":"64","author":"Anufriev","year":"2015","journal-title":"Russ. Chem. Bull."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/j.tet.2018.11.040","article-title":"Improved synthesis of icosahedral carboranes containing exopolyhedral B-C and C-C bonds","volume":"75","author":"Anderson","year":"2018","journal-title":"Tetrahedron"},{"key":"ref_43","first-page":"922","article-title":"Suzuki cross-coupling in the carborane series","volume":"68","author":"Zakharkin","year":"1998","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/S0022-328X(02)01431-6","article-title":"Palladium-catalyzed cross-coupling reactions of arylboronic acids and 2-I-p-carborane","volume":"657","author":"Eriksson","year":"2002","journal-title":"J. Organomet. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1295","DOI":"10.1002\/anie.201507697","article-title":"Palladium-catalyzed regioselective diarylation of o-Carboranes by direct cage B\u2212H activation","volume":"55","author":"Quan","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2699","DOI":"10.1002\/chem.202003634","article-title":"Rh-Catalyzed decarbonylative cross-coupling between o-carboranes and twisted amides: A regioselective, additive-free, and concise late-stage carboranylation","volume":"27","author":"Li","year":"2020","journal-title":"Chem. A Eur. J."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"14827","DOI":"10.1038\/ncomms14827","article-title":"Iridium-catalysed regioselective borylation of carboranes via direct B\u2013H activation","volume":"8","author":"Cheng","year":"2017","journal-title":"Nat. Commun."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"896","DOI":"10.1021\/ja01006a009","article-title":"Reconstruction of the 1,2-dicarbaclovododecaborane(12) structure by boron-atom insertion with (3)-1,2-dicarbollide ions","volume":"90","author":"Hawthorne","year":"1968","journal-title":"J. Am. Chem. Soc."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1239","DOI":"10.1007\/s11172-019-2547-7","article-title":"Synthesis of cobalt and nickel 6,6\u2032-diphenylbis(dicarbollides)","volume":"68","author":"Anufriev","year":"2019","journal-title":"Russ. Chem. Bull."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"9398","DOI":"10.1039\/c3cc45313h","article-title":"A three-dimensional \u03c0-electron acceptor, tri-phenyl-o-carborane, bearing a rigid conformation with end-on phenyl units","volume":"49","author":"Jin","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"6555","DOI":"10.1021\/ic010493o","article-title":"Are halocarboranes suitable for substitution reactions? The case for 3-I-1,2-closo-C2B10H11: Molecular orbital calculations, aryldehalogenation reactions, 11B NMR Interpretation of closo-carboranes, and molecular structures of 1-Ph-3-Br-1,2-closo-C2B10H10 and 3-Ph-1,2-closo-C2B10H11","volume":"40","author":"Oliva","year":"2001","journal-title":"Inorg. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"16085","DOI":"10.1021\/ja1058789","article-title":"Palladium\/Nickel-cocatalyzed cycloaddition of 1,3-dehydro-o-carborane with alkynes. Facile synthesis of C,B-substituted carboranes","volume":"132","author":"Qiu","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1016\/S0022-328X(01)01108-1","article-title":"The B-I activation in o-carborane clusters: Their fate towards B-H. Easy synthesis of [7,10-C2B10H13]\u2212","volume":"642","author":"Teixidor","year":"2002","journal-title":"J. Organomet. Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"5635","DOI":"10.1039\/C6SC01566B","article-title":"[3-N2-o-C2B10H11][BF4]: A useful synthon for multiple cage boron functionalizations of o-carborane","volume":"7","author":"Zhao","year":"2016","journal-title":"Chem. Sci."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"10199","DOI":"10.1039\/D0NJ02052D","article-title":"Synthesis and structure of 3-arylazo derivatives of ortho-carborane","volume":"44","author":"Shmalko","year":"2020","journal-title":"New J. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"369","DOI":"10.3987\/COM-09-S(S)32","article-title":"Synthesis of 3-aryl-1,2-dicarba-closo-dodecaboranes by Suzuki-Miyaura coupling reaction","volume":"80","author":"Aizawa","year":"2010","journal-title":"Heterocycles"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"9276","DOI":"10.1021\/acs.orglett.9b03790","article-title":"Old key opens the lock in carborane: The in situ NHC-Palladium catalytic system for selective arylation of B(3,6)\u2013H bonds of o-carboranes via B\u2013H activation","volume":"21","author":"Xu","year":"2019","journal-title":"Org. Lett."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4065","DOI":"10.1021\/acs.accounts.1c00460","article-title":"A strategy for selective catalytic B\u2013H functionalization of o-carboranes","volume":"54","author":"Qiu","year":"2021","journal-title":"Accounts Chem. Res."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1289","DOI":"10.1134\/S0036023621090151","article-title":"Functional group directed B\u2013H activation of polyhedral boron hydrides by transition metal complexes (Review)","volume":"66","author":"Sivaev","year":"2021","journal-title":"Russ. J. Inorg. Chem."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"Anufriev, S.A., Shmal\u2019ko, A.V., Suponitsky, K.Y., and Sivaev, I.B. (2020). One-pot synthesis of B-aryl carboranes with sensitive functional groups using sequential cobalt- and palladium-catalyzed reactions. Catalysts, 10.","DOI":"10.3390\/catal10111348"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"3867","DOI":"10.1021\/ja0289494","article-title":"New chemical synthesis of functionalized arylzinc compounds from aromatic or thienyl bromides under mild conditions using a simple cobalt catalyst and zinc dust","volume":"125","author":"Fillon","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"6417","DOI":"10.1016\/S0040-4039(03)01595-8","article-title":"New progress in the cobalt-catalysed synthesis of aromatic organozinc compounds by reduction of aromatic halides by zinc dust","volume":"44","author":"Kazmierski","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"568","DOI":"10.1002\/ijch.201000032","article-title":"cobalt-catalyzed cross-coupling reactions of aryl halides","volume":"50","author":"Gosmini","year":"2010","journal-title":"Isr. J. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1007\/s11172-008-0120-x","article-title":"Some aspects of the chemical behavior of icosahedral carboranes","volume":"57","author":"Kalinin","year":"2008","journal-title":"Russ. Chem. Bull."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1937","DOI":"10.1016\/j.tetlet.2006.01.072","article-title":"NMR study of 1-aryl-1,2-dicarba-closo-dodecaboranes: Intramolecular C\u2013H\u22efO hydrogen bonding in solution","volume":"47","author":"Ohta","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"753","DOI":"10.1007\/s11172-021-3146-y","article-title":"Rotational conformation of 8,8\u2032-dihalogenated derivatives of cobalt bis(dicarbollide) in solution","volume":"70","author":"Sivaev","year":"2021","journal-title":"Russ. Chem. Bull."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"797","DOI":"10.1002\/mrc.1851","article-title":"13C NMR chemical shifts of carbonyl groups in substituted benzaldehydes and acetophenones: Substituent chemical shift increments","volume":"44","author":"Stanley","year":"2006","journal-title":"Magn. Reson. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"3211","DOI":"10.1021\/jz501613p","article-title":"Experimental determination of the electrostatic nature of carbonyl hydrogen-bonding interactions using IR-NMR correlations","volume":"5","author":"Kashid","year":"2014","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"7384","DOI":"10.1021\/jp953141+","article-title":"Intermolecular nonbonded contact distances in organic crystal structures: Comparison with distances expected from van der Waals Radii","volume":"100","author":"Rowland","year":"1996","journal-title":"J. Phys. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"547","DOI":"10.1007\/s11172-005-0289-1","article-title":"Nature of weak inter- and intramolecular contacts in crystals 2. Character of electron delocalization and the nature of X\u2014H...H\u2014X (X = C, B) contacts in the crystal of 1-phenyl-o-carborane","volume":"54","author":"Glukhov","year":"2005","journal-title":"Russ. Chem. Bull."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/j.poly.2018.07.009","article-title":"Synthesis of new nido-carborane based carboxylic acids and amines","volume":"153","author":"Erokhina","year":"2018","journal-title":"Polyhedron"},{"key":"ref_72","unstructured":"Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Montgomery, J.A., Kudin, K.N., Burant, J.C., and Millam, J.M. (2004). Gaussian 03, Revision E.01, Gaussian, Inc."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"4436","DOI":"10.1002\/ejic.201700785","article-title":"Synthesis of 10-methylsulfide and 10-alkylmethylsulfonium nido-carborane derivatives: B\u2013H\u22ef\u03c0 interactions between the B\u2013H\u2013B hydrogen atom and alkyne group in 10-RC\u2261CCH2S(Me)-7,8-C2B9H11","volume":"2017","author":"Anufriev","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","unstructured":"Suponitsky, K.Y., Anisimov, A.A., Anufriev, S.A., Sivaev, I.B., and Bregadze, V.I. (2021). 1,12-Diiodo-ortho-carborane: A classic textbook example of the dihalogen bond. Crystals, 11.","DOI":"10.3390\/cryst11040396"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"044109","DOI":"10.1063\/1.2936121","article-title":"Applicability of hybrid density functional theory methods to calculation of molecular hyperpolarizability","volume":"129","author":"Suponitsky","year":"2008","journal-title":"J. Chem. Phys."},{"key":"ref_76","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_77","unstructured":"Keith, T.A. (2015). AIMAll (Version 15.05.18), TK Gristmill Software."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1016\/S0009-2614(98)00036-0","article-title":"Hydrogen bond strengths revealed by topological analyses of experimentally observed electron densities","volume":"285","author":"Espinosa","year":"1998","journal-title":"Chem. Phys. Lett."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"4255","DOI":"10.1002\/asia.201901280","article-title":"Synthesis and characterization of 3-(5-(fluorodinitromethyl)-1H-1,2,4-triazol-3-yl)-4-nitrofurazan: A novel promising energetic component of boron-based fuels for rocket ramjet engines","volume":"14","author":"Sheremetev","year":"2019","journal-title":"Chem. Asian J."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"4444","DOI":"10.1002\/ejic.201700575","article-title":"Methylsulfanyl-stabilized rotamers of cobalt bis(dicarbollide)","volume":"2017","author":"Anufriev","year":"2017","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1007\/BF02558176","article-title":"Homogenous catalysis in the reactions of olefinic substances. V. Hydrogenation of soybean oil methyl ester with triphenylphosphine and triphenylarsine palladium catalysts","volume":"44","author":"Itatani","year":"1967","journal-title":"J. Am. Oil Chem. Soc."},{"key":"ref_82","doi-asserted-by":"crossref","unstructured":"Armarego, W.L.F., and Chai, C.L.L. (2009). Purification of Laboratory Chemicals, Butterworth-Heinemann. [6th ed.].","DOI":"10.1016\/B978-1-85617-567-8.50012-3"},{"key":"ref_83","unstructured":"(2021, November 24). Scientific Instrument Services (SIS). Available online: https:\/\/www.sisweb.com\/mstools\/isotope.htm."},{"key":"ref_84","unstructured":"Bruker (2014). APEX2 and SAINT, Bruker AXS Inc."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Cryst. C"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/23\/7297\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T07:38:24Z","timestamp":1760168304000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/23\/7297"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,12,1]]},"references-count":85,"journal-issue":{"issue":"23","published-online":{"date-parts":[[2021,12]]}},"alternative-id":["molecules26237297"],"URL":"https:\/\/doi.org\/10.3390\/molecules26237297","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,12,1]]}}}