{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,11]],"date-time":"2026-01-11T08:43:47Z","timestamp":1768121027507,"version":"3.49.0"},"reference-count":60,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2026,1,9]],"date-time":"2026-01-09T00:00:00Z","timestamp":1767916800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100012190","name":"Ministry of Science and Higher Education of the Russian Federation","doi-asserted-by":"crossref","award":["075-15-2024-546"],"award-info":[{"award-number":["075-15-2024-546"]}],"id":[{"id":"10.13039\/501100012190","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This work explores a novel and efficient synthetic approach to a new class of boron cluster derivatives via the nucleophilic addition of stabilized phosphorus ylides, Ph3P=CHR2 (R2 = COOEt, CN), to a series of nitrilium salts of the closo-decaborate anion, [2-B10H9NCR1]\u2212 (R1 = Me, Et, nPr, iPr, Ph). The reaction proceeds regio- and stereospecifically, affording a diverse range of iminoacyl phosphorane derivatives, [2-B10H9NH=C(R1)C(PPh3)R2]\u2212, in high isolated yields (up to 95%). The obtained compounds (10 examples) were isolated as tetrabutylammonium or tetraphenylphosphonium salts and thoroughly characterized by multinuclear NMR (11B, 1H, 13C, 31P), high-resolution mass spectrometry, and single-crystal X-ray diffraction. The reaction feasibility was found to be strongly influenced by the steric hindrance of the R1 group. Furthermore, the practical utility of these novel hybrids was demonstrated by employing the [2-B10H9NH=C(CH3)C(COOC2H5)=PPh3]\u2212 anion as a highly effective membrane-active component in ion-selective electrodes. The developed tetraphenylphosphonium (TPP+) sensor exhibited a near-Nernstian response, a low detection limit of 3 \u00d7 10\u22128 M, and excellent selectivity over a range of common inorganic and organic cations, showcasing the potential of closo-borate-based ionophores in analytical chemistry.<\/jats:p>","DOI":"10.3390\/molecules31020231","type":"journal-article","created":{"date-parts":[[2026,1,9]],"date-time":"2026-01-09T12:52:17Z","timestamp":1767963137000},"page":"231","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Nucleophilic Addition of Stabilized Phosphorus Ylides to Closo-Decaborate Nitrilium Salts: A Synthetic Route to Boron Cluster-Functionalized Iminoacyl Phosphoranes and Their Application in Potentiometric Sensing"],"prefix":"10.3390","volume":"31","author":[{"given":"Vera V.","family":"Voinova","sequence":"first","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eugeniy S.","family":"Turyshev","sequence":"additional","affiliation":[{"name":"Institute for African Studies of the Russian Academy of Sciences (IAS), st. Spiridonovka 30\/1, 123001 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Sergey S.","family":"Novikov","sequence":"additional","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia"},{"name":"Faculty of Fundamental Physical and Chemical Engineering, Lomonosov Moscow State University, Leninskie Gory 1, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7426-5982","authenticated-orcid":false,"given":"Nikita A.","family":"Selivanov","sequence":"additional","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alexander Yu.","family":"Bykov","sequence":"additional","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ilya N.","family":"Klyukin","sequence":"additional","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4083-386X","authenticated-orcid":false,"given":"Andrey P.","family":"Zhdanov","sequence":"additional","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6363-5535","authenticated-orcid":false,"given":"Mikhail S.","family":"Grigoriev","sequence":"additional","affiliation":[{"name":"Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskii pr. 31, Bldg 4, 119071 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4475-124X","authenticated-orcid":false,"given":"Konstantin Yu.","family":"Zhizhin","sequence":"additional","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Nikolay T.","family":"Kuznetsov","sequence":"additional","affiliation":[{"name":"N.S. Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii pr.31, 119991 Moscow, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2026,1,9]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Druzina, A.A., Grammatikova, N.E., Zhidkova, O.B., Nekrasova, N.A., Dudarova, N.V., Kosenko, I.D., Grin, M.A., and Bregadze, V.I. (2022). Synthesis and Antibacterial Activity Studies of the Conjugates of Curcumin with Closo-Dodecaborate and Cobalt Bis(Dicarbollide) Boron Clusters. Molecules, 27.","DOI":"10.3390\/molecules27092920"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"322","DOI":"10.1021\/acscentsci.1c01132","article-title":"Natural-Product-Directed Catalytic Stereoselective Synthesis of Functionalized Fused Borane Cluster\u2013Oxazoles for the Discovery of Bactericidal Agents","volume":"8","author":"Varkhedkar","year":"2022","journal-title":"ACS Cent. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"e01842","DOI":"10.1002\/asia.202401842","article-title":"Alternative Approach to Avoid Drug Resistance: Polyhedral Inorganic and Metallomacrobicyclic 3D-Shaped Guests Strongly Binding to Allosteric Sites and\/or Macromolecular Interfaces","volume":"20","author":"Voloshin","year":"2025","journal-title":"Chem. Asian J."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"421","DOI":"10.1007\/s00775-022-01937-4","article-title":"New Type of RNA Virus Replication Inhibitor Based on Decahydro-Closo-Decaborate Anion Containing Amino Acid Ester Pendant Group","volume":"27","author":"Avdeeva","year":"2022","journal-title":"JBIC J. Biol. Inorg. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"30750","DOI":"10.1016\/j.ijhydene.2021.06.196","article-title":"Direct Conversion of Methane into Methanol and Ethanol via Spherical Au@Cs2[Closo-B12H12] and Pd@Cs2[Closo-B12H12] Nanoparticles","volume":"46","author":"Wang","year":"2021","journal-title":"Int. J. Hydrogen Energy"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"8697","DOI":"10.1021\/acs.jpclett.3c02222","article-title":"Catalytic Potential of [B12X11]2\u2212 (X = F, Cl, Br, I, CN) Dianions","volume":"14","author":"Jena","year":"2023","journal-title":"J. Phys. Chem. Lett."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"47706","DOI":"10.1021\/acsami.2c12759","article-title":"Evaluating Electrolyte\u2013Anode Interface Stability in Sodium All-Solid-State Batteries","volume":"14","author":"Deysher","year":"2022","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"782","DOI":"10.1016\/j.ensm.2019.08.032","article-title":"Status and Prospects of Hydroborate Electrolytes for All-Solid-State Batteries","volume":"25","author":"Remhof","year":"2020","journal-title":"Energy Storage Mater."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"42511","DOI":"10.1021\/acsami.3c07242","article-title":"Order-Disorder Phase Transition and Ionic Conductivity in a Li2B12H12 Solid Electrolyte","volume":"15","author":"Maltsev","year":"2023","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"406","DOI":"10.1002\/cac2.12089","article-title":"Boron Neutron Capture Therapy: Current Status and Future Perspectives","volume":"40","author":"Dymova","year":"2020","journal-title":"Cancer Commun."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"868","DOI":"10.1080\/09553002.2020.1761039","article-title":"Accelerator-Based Boron Neutron Capture Therapy for Malignant Glioma: A Pilot Neutron Irradiation Study Using Boron Phenylalanine, Sodium Borocaptate and Liposomal Borocaptate with a Heterotopic U87 Glioblastoma Model in SCID Mice","volume":"96","author":"Zavjalov","year":"2020","journal-title":"Int. J. Radiat. Biol."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Seneviratne, D.S., Saifi, O., Mackeyev, Y., Malouff, T., and Krishnan, S. (2023). Next-Generation Boron Drugs and Rational Translational Studies Driving the Revival of BNCT. Cells, 12.","DOI":"10.3390\/cells12101398"},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Ryabchikova, M.N., Nelyubin, A.V., Klyukin, I.N., Selivanov, N.A., Bykov, A.Y., Kubasov, A.S., Skribitsky, V.A., Finogenova, Y.A., Shpakova, K.E., and Kasianov, A.A. (2024). Synthesis of New Promising BNCT Agents Based on Conjugates of Closo-Dodecaborate Anion and Aliphatic Diamino Acids. Int. J. Mol. Sci., 26.","DOI":"10.20944\/preprints202412.0021.v1"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"977","DOI":"10.1039\/b715363e","article-title":"Cyclic Oxonium Derivatives of Polyhedral Boron Hydrides and Their Synthetic Applications","volume":"11","author":"Semioshkin","year":"2008","journal-title":"Dalton Trans."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3318","DOI":"10.1039\/c2cs35441a","article-title":"Methods to Produce B\u2013C, B\u2013P, B\u2013N and B\u2013S Bonds in Boron Clusters","volume":"42","author":"Olid","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"119589","DOI":"10.1016\/j.ica.2020.119589","article-title":"The Method for Synthesis of 2-Sulfonium Closo-Decaborate Anions Derivatives with Exo-Polyhedral Aminogroups","volume":"507","author":"Kubasov","year":"2020","journal-title":"Inorg. Chim. Acta"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"823","DOI":"10.1002\/cmdc.201800793","article-title":"Design, Synthesis, and Evaluation of Lipopeptide Conjugates of Mercaptoundecahydrododecaborate for Boron Neutron Capture Therapy","volume":"14","author":"Isono","year":"2019","journal-title":"ChemMedChem"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"574","DOI":"10.1016\/j.ejmech.2015.02.033","article-title":"New Functionalized Mercaptoundecahydrododecaborate Derivatives for Potential Application in Boron Neutron Capture Therapy: Synthesis, Characterization and Dynamic Visualization in Cells","volume":"93","author":"Genady","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1698","DOI":"10.1016\/j.jorganchem.2008.12.053","article-title":"N-Arylammonio- and N-Pyridinium-Substituted Derivatives of Dodecahydro-Closo-Dodecaborate(2-)","volume":"694","author":"Lork","year":"2009","journal-title":"J. Organomet. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2757","DOI":"10.1016\/j.jorganchem.2005.02.037","article-title":"B12H11-Containing Guanidinium Derivatives by Reaction of Carbodiimides with H3N\u2013B12H11(1\u2212). A New Method for Connecting Boron Clusters to Organic Compounds","volume":"690","author":"Hoffmann","year":"2005","journal-title":"J. Organomet. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"6576","DOI":"10.1002\/anie.201411858","article-title":"Functionalization of Closo -Borates via Iodonium Zwitterions","volume":"54","author":"Ringstrand","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"135324","DOI":"10.1016\/j.molstruc.2023.135324","article-title":"[Closo-B10H8-1,10-(NHC(NH2)Me)2]: A Rare Zwitterionic Amidinium Derivative","volume":"1284","author":"Hietsoi","year":"2023","journal-title":"J. Mol. Struct."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"851","DOI":"10.1039\/D1CC06485A","article-title":"[Closo-B10H8-1,10-(COOH)2]2\u2212: A Building Block for Functional Materials?","volume":"58","author":"Hietsoi","year":"2022","journal-title":"Chem. Commun."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"505","DOI":"10.6060\/mhc171254z","article-title":"Synthesis of New Bioinorganic Systems Based on Nitrilium Derivatives of Closo-Decaborate Anion and Meso-Arylporphyrins with Pendant Amino Groups","volume":"10","author":"Ezhov","year":"2017","journal-title":"Macroheterocycles"},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Nelyubin, A.V., Selivanov, N.A., Bykov, A.Y., Klyukin, I.N., Novikov, A.S., Zhdanov, A.P., Karpechenko, N.Y., Grigoriev, M.S., Zhizhin, K.Y., and Kuznetsov, N.T. (2021). Primary Amine Nucleophilic Addition to Nitrilium Closo-Dodecaborate [B12H11NCCH3]\u2212: A Simple and Effective Route to the New BNCT Drug Design. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms222413391"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Voinova, V.V., Selivanov, N.A., Plyushchenko, I.V., Vokuev, M.F., Bykov, A.Y., Klyukin, I.N., Novikov, A.S., Zhdanov, A.P., Grigoriev, M.S., and Rodin, I.A. (2021). Fused 1,2-Diboraoxazoles Based on Closo-Decaborate Anion\u2013Novel Members of Diboroheterocycle Class. Molecules, 26.","DOI":"10.3390\/molecules26010248"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"983","DOI":"10.1080\/10426507.2019.1631312","article-title":"Nitrilium Derivatives of Polyhedral Boron Compounds (Boranes, Carboranes, Metallocarboranes): Synthesis and Reactivity","volume":"194","author":"Stogniy","year":"2019","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3051","DOI":"10.1039\/D1DT04174F","article-title":"Nucleophilic Addition Reactions to Nitrilium Derivatives [B12H11NCCH3]\u2212 and [B12H11NCCH2CH3]\u2212. Synthesis and Structures of Closo -Dodecaborate-Based Iminols, Amides and Amidines","volume":"51","author":"Laskova","year":"2022","journal-title":"Dalton Trans."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1075","DOI":"10.1002\/cplu.201200257","article-title":"Coupling of Azomethine Ylides with Nitrilium Derivatives of Closo -Decaborate Clusters: A Synthetic and Theoretical Study","volume":"77","author":"Mindich","year":"2012","journal-title":"Chempluschem"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"372","DOI":"10.1016\/j.ica.2017.11.054","article-title":"Push-Pull Alkenes Bearing Closo-Decaborate Cluster Generated via Nucleophilic Addition of Carbanions to Borylated Nitrilium Salts","volume":"471","author":"Daines","year":"2018","journal-title":"Inorganica Chim. Acta"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"2016","DOI":"10.1039\/D0SC03278F","article-title":"Phosphorus-Ylides: Powerful Substituents for the Stabilization of Reactive Main Group Compounds","volume":"12","author":"Sarbajna","year":"2021","journal-title":"Chem. Sci."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"11838","DOI":"10.1021\/acs.joc.5c01055","article-title":"Synthesis of 1-Fluoroalkyl-5-Substituted-1,2,3-Triazoles from Carbonyl-Stabilized Phosphonium Ylides","volume":"90","author":"Filgas","year":"2025","journal-title":"J. Org. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1608","DOI":"10.1021\/acsmacrolett.3c00524","article-title":"Unveiling the Antifouling Potential of Stabilized Poly(Phosphorus Ylides)","volume":"12","author":"Karagrigoriou","year":"2023","journal-title":"ACS Macro Lett."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1608","DOI":"10.1021\/acs.organomet.4c00204","article-title":"Groups 9 and 10 Complexes of C\u2013Donor Ligands Derived from Pyridinium-Stabilized Phosphorus Ylides","volume":"43","author":"Poddar","year":"2024","journal-title":"Organometallics"},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Turyshev, E.S., Golubev, A.V., Bykov, A.Y., Zhizhin, K.Y., and Kuznetsov, N.T. (2025). Preparation of a New Active Component 1,10-B10H8(S(C18H37)2)2 for Potentiometric Membranes for the Determination of Terbinafine Hydrochloride. Inorganics, 13.","DOI":"10.20944\/preprints202411.2079.v1"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"123239","DOI":"10.1016\/j.talanta.2022.123239","article-title":"Potentiometric Quantitation of General Local Anesthetics with a New Highly Sensitive Membrane Sensor","volume":"241","author":"Turyshev","year":"2022","journal-title":"Talanta"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3617","DOI":"10.1021\/ic00019a009","article-title":"Platinum-Assisted Addition of Carbonyl-Stabilized Phosphorus Ylides to Benzonitrile to Give Iminophosphorane Complexes of Platinum(II). Crystal and Molecular Structure of Trans-[PtCl2{E-N(:PPh3)C(Ph):CHCO2Et}(NCPh)].Cntdot.1\/2Me2CO.","volume":"30","author":"Vicente","year":"1991","journal-title":"Inorg. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"5441","DOI":"10.1021\/ic00126a012","article-title":"Platinum-Assisted C-C Bond Formation. Synthesis of Platinum Imidoyl Phosphorus Ylide Complexes and the First Crystal Structure of an Imidoyl Phosphorus Ylide Complex","volume":"34","author":"Vicente","year":"1995","journal-title":"Inorg. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"1015","DOI":"10.1021\/jo01015a015","article-title":"The Reaction of Stable Phosphoranes with Acid Anhydrides. A New Synthesis of Acetylenic Ketones","volume":"30","author":"Chopard","year":"1965","journal-title":"J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","unstructured":"Aitken, R.A., Karodia, N., and Lightfoot, P. (2000). The Solid State Conformation of Oxo Stabilised Ylides: X-Ray Structures of Four New Polyoxo Phosphorus Ylides. J. Chem. Soc. Perkin Trans. 2, 333\u2013340.","DOI":"10.1039\/a905747a"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1794","DOI":"10.1039\/C5OB02467F","article-title":"Synthesis, Structure and Pyrolysis of Stabilised Phosphonium Ylides Containing Saturated Oxygen Heterocycles","volume":"14","author":"Aitken","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"284","DOI":"10.1016\/j.molstruc.2011.08.022","article-title":"Molecular Structures and Preferred Conformations of Stabilized Keto Diester Phosphonium Ylides","volume":"1004","author":"Silva","year":"2011","journal-title":"J. Mol. Struct."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"432","DOI":"10.3184\/0308234041423637","article-title":"Reactions of \u03b2-Oxo-\u03b1,\u03b2-Bis(Alkoxycarbonyl)Phosphonium Ylides Based on P-Heterocycles","volume":"2004","author":"Keglevich","year":"2004","journal-title":"J. Chem. Res."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"15257","DOI":"10.1002\/chem.201904131","article-title":"A Highly Stabilized Phosphonium Ylide That Forms Supramolecular Dimers in Solution and the Solid State","volume":"25","author":"Kim","year":"2019","journal-title":"Chem. A Eur. J."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"710","DOI":"10.3184\/030823410X12857507693419","article-title":"X-Ray Crystal Structures of Ethoxycarbonyl-, Diethyl-2-Triphenyl-\u039b5-Phosphoranylidene-N.-Phenylimide Derivatives","volume":"34","author":"Arsanious","year":"2010","journal-title":"J. Chem. Res."},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R. (1987). Tables of Bond Lengths Determined by X-Ray and Neutron Diffraction. Part I. Bond Lengths in Organic Compounds. J. Chem. Soc. Perkin Trans. 2, S1\u2013S19.","DOI":"10.1039\/p298700000s1"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"2527","DOI":"10.1351\/pac199466122527","article-title":"Recommendations for Nomenclature of Ionselective Electrodes (IUPAC Recommendations 1994)","volume":"66","author":"Buck","year":"1994","journal-title":"Pure Appl. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/0026-265X(79)90047-X","article-title":"Extraction-Spectrophotometric Determination of Palladium with Triphenylphosphine (TPP)","volume":"24","author":"Mojski","year":"1979","journal-title":"Microchem. J."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1016\/0026-265X(84)90039-0","article-title":"Extraction and Spectrophotometric Determination of Niobium by Tetraphenylarsonium and Phosphonium Chloride from a Hydrochloric Acid Solution","volume":"30","author":"Tamhina","year":"1984","journal-title":"Microchem. J."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"319","DOI":"10.1016\/j.aca.2004.11.085","article-title":"Chemical Speciation of Chromium(III, VI) Employing Extractive Spectrophotometry and Tetraphenylarsonium Chloride or Tetraphenylphosphonium Bromide as Ion-Pair Reagent","volume":"534","author":"Hassan","year":"2005","journal-title":"Anal. Chim. Acta"},{"key":"ref_51","unstructured":"(APEX2, 2006). APEX2, version 2.1-0."},{"key":"ref_52","unstructured":"(SADABS, 2004). SADABS, version 2004\/1."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A Short History of SHELX","volume":"64","author":"Sheldrick","year":"2007","journal-title":"Acta Crystallogr. A"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT\u2014Integrated Space-Group and Crystal-Structure Determination","volume":"71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. A"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A Complete Structure Solution, Refinement and Analysis Program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Crystallogr."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2250","DOI":"10.1021\/ac00086a009","article-title":"Response Mechanism of Polymer Membrane-Based Potentiometric Polyion Sensors","volume":"66","author":"Fu","year":"1994","journal-title":"Anal. Chem."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"8351","DOI":"10.1021\/jo101589h","article-title":"Drying of Organic Solvents: Quantitative Evaluation of the Efficiency of Several Desiccants","volume":"75","author":"Williams","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4528","DOI":"10.1002\/chem.201800313","article-title":"Enantioselective Alkylation of 2-Oxindoles Catalyzed by a Bifunctional Phase-Transfer Catalyst: Synthesis of (\u2212)-Debromoflustramine\u2005B","volume":"24","author":"Craig","year":"2018","journal-title":"Chem. A Eur. J."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1987","DOI":"10.1021\/ja065790c","article-title":"CH Activation Reactions of Ruthenium N-Heterocyclic Carbene Complexes: Application in a Catalytic Tandem Reaction Involving CC Bond Formation from Alcohols","volume":"129","author":"Burling","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"468","DOI":"10.1134\/S0036023617040210","article-title":"Hydrolysis of Nitrilium Derivatives of the Closo-Decaborate Anion [2-B10H9(N\u2261CR)]\u2013 (R = CH3, C2H5, C(CH3)3, or C6H5)","volume":"62","author":"Zhdanov","year":"2017","journal-title":"Russ. J. Inorg. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/2\/231\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,1,11]],"date-time":"2026-01-11T05:23:29Z","timestamp":1768109009000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/31\/2\/231"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,1,9]]},"references-count":60,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2026,1]]}},"alternative-id":["molecules31020231"],"URL":"https:\/\/doi.org\/10.3390\/molecules31020231","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,1,9]]}}}