{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,27]],"date-time":"2025-10-27T16:09:18Z","timestamp":1761581358771,"version":"build-2065373602"},"reference-count":62,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2015,10,21]],"date-time":"2015-10-21T00:00:00Z","timestamp":1445385600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia","doi-asserted-by":"publisher","award":["UID\/QUI\/00100\/2013"],"award-info":[{"award-number":["UID\/QUI\/00100\/2013"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Council of Scientific and Industrial Research, New Delhi"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Microwave assisted synthesis of the Cu(I) compound [Cu(\u00b54-4-ptz)]n [1, 4-ptz = 5-(4-pyridyl)tetrazolate] has been performed by employing a relatively easy method and within a shorter period of time compared to its sister compounds. The syntheses of the Cu(II) compounds [Cu3(\u00b53-4-ptz)4(\u00b52-N3)2(DMF)2]n\u2219(DMF)2n (2) and [Cu(\u00b52-4-ptz)2(H2O)2]n (3) using a similar method were reported previously by us. MOFs 1-3 revealed high catalytic activity toward oxidation of cyclic alkanes (cyclopentane, -hexane and -octane) with aqueous hydrogen peroxide, under very mild conditions (at room temperature), without any added solvent or additive. The most efficient system (2\/H2O2) showed, for the oxidation of cyclohexane, a turnover number (TON) of 396 (TOF of 40 h\u22121), with an overall product yield (cyclohexanol and cyclohexanone) of 40% relative to the substrate. Moreover, the heterogeneous catalytic systems 1\u20133 allowed an easy catalyst recovery and reuse, at least for four consecutive cycles, maintaining ca. 90% of the initial high activity and concomitant high selectivity.<\/jats:p>","DOI":"10.3390\/molecules201019203","type":"journal-article","created":{"date-parts":[[2015,10,22]],"date-time":"2015-10-22T03:05:31Z","timestamp":1445483131000},"page":"19203-19220","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Greener Selective Cycloalkane Oxidations with Hydrogen Peroxide Catalyzed by Copper-5-(4-pyridyl)tetrazolate  Metal-Organic Frameworks"],"prefix":"10.3390","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5403-9352","authenticated-orcid":false,"given":"Lu\u00edsa","family":"Martins","sequence":"first","affiliation":[{"name":"Chemical Engineering Departament, Instituto Superior de Engenharia de Lisboa,  Instituto Polit\u00e9cnico de Lisboa, R. Conselheiro Em\u00eddio Navarro, 1959-007 Lisboa, Portugal"},{"name":"Centro de Qu\u00edmica Estrutural, Complexo I, Instituto Superior T\u00e9cnico, Universidade de Lisboa,  Av. Rovisco Pais, 1049-001 Lisboa, Portugal"}]},{"given":"Rajendar","family":"Nasani","sequence":"additional","affiliation":[{"name":"Department of Chemistry, School of Basic Sciences, Indian Institute of Technology Indore,  IET-DAVV Campus, Khandwa Road, Indore 452017, India"}]},{"given":"Manideepa","family":"Saha","sequence":"additional","affiliation":[{"name":"Department of Chemistry, School of Basic Sciences, Indian Institute of Technology Indore,  IET-DAVV Campus, Khandwa Road, Indore 452017, India"}]},{"given":"Shaikh","family":"Mobin","sequence":"additional","affiliation":[{"name":"Department of Chemistry, School of Basic Sciences, Indian Institute of Technology Indore,  IET-DAVV Campus, Khandwa Road, Indore 452017, India"}]},{"given":"Suman","family":"Mukhopadhyay","sequence":"additional","affiliation":[{"name":"Department of Chemistry, School of Basic Sciences, Indian Institute of Technology Indore,  IET-DAVV Campus, Khandwa Road, Indore 452017, India"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8323-888X","authenticated-orcid":false,"given":"Armando","family":"Pombeiro","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural, Complexo I, Instituto Superior T\u00e9cnico, Universidade de Lisboa,  Av. Rovisco Pais, 1049-001 Lisboa, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2015,10,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/j.inoche.2012.09.002","article-title":"A hexa-nuclear {Cu6(ptz)6} cluster containing five [Cu2N4] units with cycle connecting cycle mode induced by tetrazole-based ligand to modify Keggin anions","volume":"25","author":"Wang","year":"2012","journal-title":"Inorg. Chem. Commun."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"1667","DOI":"10.1039\/C2DT31951A","article-title":"Secondary spacer modulated assembly of polyoxometalate based metal\u2013organic frameworks","volume":"42","author":"Sha","year":"2013","journal-title":"Dalton Trans."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1016\/j.ica.2012.06.008","article-title":"Solid state coordination chemistry of copper with pyridyltetrazoles: Structural consequences of incorporation of coordinating anions","volume":"392","author":"Darling","year":"2012","journal-title":"Inorg. Chim. Acta"},{"key":"ref_4","first-page":"765","article-title":"Tetrazoles: LI. Synthesis of 5-Substituted Tetrazoles under Microwave Activation","volume":"43","author":"Myznikov","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"9983","DOI":"10.1021\/ja030204q","article-title":"Why Is Tetrazole Formation by Addition of Azide to Organic Nitriles Catalyzed by Zinc(II) Salts?","volume":"125","author":"Himo","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"2624","DOI":"10.1080\/00397910903318583","article-title":"Amine Salt\u2013Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles","volume":"40","author":"Zhou","year":"2010","journal-title":"Synth. Commun."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"8440","DOI":"10.1002\/anie.200701045","article-title":"1,3-Dipolar Cycloaddition: Click Chemistry for the Synthesis of 5-Substituted Tetrazoles from Organoaluminum Azides and Nitriles","volume":"46","author":"Aureggi","year":"2007","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"9944","DOI":"10.1039\/C4DT00531G","article-title":"Copper-organic frameworks assembled from in-situ generated 5-(4-pyridyl)tetrazole building blocks: Synthesis, structural features, topological analysis and catalytic oxidation of alcohols","volume":"43","author":"Nasani","year":"2014","journal-title":"Dalton Trans."},{"key":"ref_9","doi-asserted-by":"crossref","unstructured":"Pombeiro, A.J.L. (2014). Advances in Organometallic Chemistry and Catalysis, The Silver\/Gold Jubilee ICOMC Celebratory Book, John Wiley & Sons.","DOI":"10.1002\/9781118742952"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2741","DOI":"10.1016\/j.ccr.2012.07.022","article-title":"Multicopper complexes and coordination polymers for mild oxidative functionalization of alkanes","volume":"256","author":"Kirillov","year":"2012","journal-title":"Coord. Chem. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1016\/j.ccr.2014.01.013","article-title":"Tris(pyrazol-1yl)methane metal complexes for catalytic mild oxidative functionalizations of alkanes, alkenes and ketones","volume":"265","author":"Martins","year":"2014","journal-title":"Coord. Chem. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2303","DOI":"10.1021\/acs.cgd.5b00083","article-title":"Novel Coordination Polymers with (Pyrazolato)-based Tectons: Catalytic Activity in the Peroxidative Oxidation of Alcohols and Cyclohexane","volume":"15","author":"Timokhin","year":"2015","journal-title":"Cryst. Growth Des."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Di Nicola, C., Garau, F., Karabach, Y.Y., Martins, L.M.D.R.S., Monari, M., Pandolfo, L., Pettinari, C., and Pombeiro, A.J.L. (2009). Trinuclear Triangular Copper(II) Clusters. Synthesis, Electrochemical Studies and Catalytic Peroxidative Oxidation of Cycloalkanes. Eur. J. Inorg. Chem., 666\u2013676.","DOI":"10.1002\/ejic.200800842"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3959","DOI":"10.1002\/ejic.201500440","article-title":"Trinuclear Cu(II) structural isomers: Coordination, magnetism, electrochemistry and catalytic activity toward oxidation of alkanes","volume":"2015","author":"Sutradhar","year":"2015","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3887","DOI":"10.1021\/ja310866k","article-title":"Introducing Copper as Catalyst for Oxidative Alkane Dehydrogenation","volume":"135","author":"Conde","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1288","DOI":"10.1039\/c2cc37829a","article-title":"Oxidation of cycloalkanes by H2O2 using a copper\u2013hemicryptophane complex as a catalyst","volume":"49","author":"Perraud","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"2822","DOI":"10.1039\/c0dt01527j","article-title":"Complexes of copper(II) with 3-(ortho-substituted phenylhydrazo)pentane-2,4-diones: Syntheses, properties and catalytic activity for cyclohexane oxidation","volume":"40","author":"Kopylovich","year":"2011","journal-title":"Dalton Trans."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Clerici, M.G., and Kholdeeva, O. (2013). Liquid Phase Oxidation via Heterogeneous Catalysis, Organic Synthesis and Industrial Applications, John Wiley & Sons. Chapter 8.","DOI":"10.1002\/9781118356760"},{"key":"ref_19","unstructured":"Weissermel, K., and Arpe, H.J. (1993). Industrial Organic Chemistry, VCH Press. [2nd ed.]."},{"key":"ref_20","doi-asserted-by":"crossref","unstructured":"Clark, J.H., and Macquarrie, D.J. (2002). Handbook of Green Chemistry and Technology, Wiley.","DOI":"10.1002\/9780470988305"},{"key":"ref_21","unstructured":"(2002). Ullmann\u2019s Encyclopedia of Industrial Chemistry, Wiley-VCH. [6th ed.]."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"4083","DOI":"10.1016\/j.jorganchem.2004.07.034","article-title":"Organometallic alkane CH activation","volume":"689","author":"Crabtree","year":"2004","journal-title":"J. Organomet. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Shilov, A.E., and Shul\u2019pin, G.B. (2000). Activation and Catalytic Reactions of Saturated Hydrocarbons in the Presence of Metal Complexes, Kluwer Academic Publishers.","DOI":"10.1007\/0-306-46945-6"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Beller, M., and Bolm, C. (2004). Transition Metals for Organic Synthesis, Wiley-VCR. [2nd ed.].","DOI":"10.1002\/9783527619405"},{"key":"ref_25","doi-asserted-by":"crossref","unstructured":"Derouane, E.G., Parmon, V., Lemos, F., and R\u00e2moa Ribeiro, F. (2005). Sustainable Strategies for the Upgrading of Natural Gas: Fundamentals, Challenges, and Opportunities, Springer.","DOI":"10.1007\/1-4020-3310-9"},{"key":"ref_26","doi-asserted-by":"crossref","unstructured":"Sheldon, R.A., Arends, I., and Hanefeld, U. (2007). Green Chemistry and Catalysis, Wiley-VCH.","DOI":"10.1002\/9783527611003"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/S0926-860X(01)00472-0","article-title":"Cyclohexane oxidation continues to be a challenge","volume":"211","author":"Schuchardt","year":"2001","journal-title":"Appl. Catal. A Gen."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1007\/BF02070104","article-title":"Formation of alkyl peroxides in oxidation of alkanes by H2O2 catalyzed by transition metal complexes","volume":"48","author":"Nizova","year":"1992","journal-title":"React. Kinet. Catal. Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1006\/jcat.1993.1196","article-title":"Efficient H2O2 Oxidation of Alkanes and Arenes to Alkyl Peroxides and Phenols Catalyzed by the System Vanadate-Pyrazine-2-Carboxylic Acid","volume":"142","author":"Attanasio","year":"1993","journal-title":"J. Catal."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"6487","DOI":"10.1016\/0040-4039(96)01418-9","article-title":"Methyltrioxorhenium catalyzed oxidation of saturated and aromatic hydrocarbons by H2O2 in air","volume":"37","author":"Schuchardt","year":"1996","journal-title":"Tetrahedron Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/S1381-1169(02)00196-6","article-title":"Metal-catalyzed hydrocarbon oxygenations in solutions: The dramatic role of additives: A review","volume":"189","year":"2002","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1002\/adsc.200303147","article-title":"Hydrogen Peroxide Oxygenation of Alkanes Including Methane and Ethane Catalyzed by Iron Complexes in Acetonitrile","volume":"346","author":"Nizova","year":"2004","journal-title":"Adv. Synth. Catal."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1016\/j.apcata.2004.06.031","article-title":"Oxidation of cyclohexane with molecular oxygen using heterogeneous silica gel catalyst bonded with [1,2-bis(salicylidene amino)-phenylene] zirconium complex","volume":"273","author":"Anisia","year":"2004","journal-title":"Appl. Catal. A Gen."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Clerici, M.G., and Kholdeeva, O. (2013). Liquid Phase Oxidation via Heterogeneous Catalysis, Organic Synthesis and Industrial Applications, John Wiley & Sons. Chapter 1.","DOI":"10.1002\/9781118356760"},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Mukhopadhyay, S., Lasri, J., Charmier, M.A.J., Silva, M.F.C.G., and Pombeiro, A.J.L. (2007). Microwave synthesis of mono- and bis-tetrazolato complexes via 1,3-dipolar cycloaddition of organonitriles with platinum(II)-bound azides. Dalton Trans., 5297\u20135304.","DOI":"10.1039\/b709959b"},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Smolenski, P., Mukhopadhyay, S., Guedes Silva, M.F.C., Charmier, M.A.J., and Pombeiro, A.J.L. (2008). New water-soluble azido- and derived tetrazolato-platinum(II) complexes with PTA. Easy metal-mediated synthesis and isolation of 5-substituted tetrazoles. Dalton Trans., 6546\u20136555.","DOI":"10.1039\/b808156e"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1016\/S1631-0748(03)00021-3","article-title":"Metal-catalysed hydrocarbon oxidations","volume":"6","year":"2003","journal-title":"C. R. Chim."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"10480","DOI":"10.1021\/ic901576r","article-title":"Extremely Efficient Alkane Oxidation by a New Catalytic Reagent H2O2\/Os3(CO)12\/Pyridine","volume":"48","author":"Kozlov","year":"2009","journal-title":"Inorg. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1002\/aoc.1641","article-title":"Oxidation of alkanes and alcohols with hydrogen peroxide catalyzed by complex Os3(CO)10(\u00b5-H)2","volume":"24","author":"Kozlov","year":"2010","journal-title":"Appl. Organomet. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"12794","DOI":"10.1039\/c3dt51004b","article-title":"C\u2013H functionalization: thoroughly tuning ligands at a metal ion, a chemist can greatly enhance catalyst\u2019s activity and selectivity","volume":"42","year":"2013","journal-title":"Dalton Trans."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Pombeiro, A.J.L. (2014). Advances in Organometallic Chemistry and Catalysis, the Silver\/Gold Jubilee ICOMC Celebratory Book, John Wiley & Sons. Chapter 22.","DOI":"10.1002\/9781118742952"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"14388","DOI":"10.1039\/c3dt50966d","article-title":"Hexanuclear and Undecanuclear Iron(III) Carboxylates as Catalyst Precursors for Cyclohexane Oxidation","volume":"42","author":"Milunovic","year":"2013","journal-title":"Dalton Trans."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"11229","DOI":"10.1021\/ic3017062","article-title":"A Hexanuclear Oxovanadium(IV,V) Complex Bearing N,O-Ligand as a Highly Efficient Alkane Oxidation Catalyst","volume":"51","author":"Sutradhar","year":"2012","journal-title":"Inorg. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1132","DOI":"10.1002\/asia.201301331","article-title":"Cobalt complexes with pyrazole ligands as catalysts for the peroxidative oxidation of cyclohexane. XAS studies and biological applications","volume":"9","author":"Silva","year":"2014","journal-title":"Chem. Asian J."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"706","DOI":"10.1002\/adsc.200700529","article-title":"Scorpionate vanadium, iron and copper complexes as selective catalysts for the peroxidative oxidation of cyclohexane under mild conditions","volume":"350","author":"Silva","year":"2008","journal-title":"Adv. Synth. Catal."},{"key":"ref_46","doi-asserted-by":"crossref","unstructured":"Contaldi, S., di Nicola, C., Garau, F., Karabach, Y.Y., Martins, L.M.D.R.S., Monari, M., Pandolfo, L., Pettinari, C., and Pombeiro, A.J.L. (2009). New coordination polymers based on triangular [Cu3(m3-OH)(m-pz)3]2+ units and unsaturated carboxylates. Molecular structures, electrochemical behaviour and catalytic peroxidative oxidation of cycloalkanes. Dalton Trans., 4928\u20134941.","DOI":"10.1039\/b823370e"},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Silva, T.F.S., Mishra, G.S., Silva, M.F.G., Wanke, R., Martins, L.M.D.R.S., and Pombeiro, A.J.L. (2009). CuII complexes bearing the 2,2,2-tris(1-pyrazolyl)ethanol or 2,2,2-tris(1-pyrazolyl)ethyl methanesulfonate scorpionates. X-ray structural characterization and application in the mild catalytic peroxidative oxidation of cyclohexane. Dalton Trans., 9207\u20139215.","DOI":"10.1039\/b911990f"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"9110","DOI":"10.1021\/ic301460q","article-title":"Heterometallic CoIII4FeIII2 Schiff Base Complex: Structure, Electron Paramagnetic Resonance, and Alkane Oxidation Catalytic Activity","volume":"51","author":"Nesterov","year":"2012","journal-title":"Inorg. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1002\/adsc.200900660","article-title":"Novel scorpionate and pyrazole dioxovanadium complexes, catalysts for carboxylation and peroxidative oxidation of alkanes","volume":"352","author":"Silva","year":"2010","journal-title":"Adv. Synth. Catal."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1310","DOI":"10.1016\/j.jorganchem.2010.12.036","article-title":"Synthesis and structural characterization of iron complexes with 2,2,2-tris(1-pyrazolyl)ethanol ligands: application in the peroxidative oxidation of cyclohexane under mild conditions","volume":"696","author":"Silva","year":"2011","journal-title":"J. Organomet. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1217","DOI":"10.1351\/PAC-CON-08-10-08","article-title":"Scorpionate V(III-V) Complexes as Catalyst Precursors for Solvent-free Cyclohexane Oxidation with Dioxygen","volume":"81","author":"Mishra","year":"2009","journal-title":"Pure Appl. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1016\/j.molcata.2012.10.024","article-title":"Pyrazole or tris(pyrazolyl)ethanol oxo-vanadium(IV) complexes as homogeneous or supported catalysts for oxidation of cyclohexane under mild conditions","volume":"367","author":"Silva","year":"2013","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"3847","DOI":"10.1002\/cctc.201300432","article-title":"Heterogenisation of a C-scorpionate Fe(II) complex in carbon materials for cyclohexane oxidation with hydrogen peroxide","volume":"5","author":"Martins","year":"2013","journal-title":"ChemCatChem"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"43","DOI":"10.1016\/j.apcata.2013.05.022","article-title":"Gold Nanoparticles Supported on Carbon Materials for Cyclohexane Oxidation with Hydrogen Peroxide","volume":"464\u2013465","author":"Martins","year":"2013","journal-title":"Appl. Cat. A Gen."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.molcata.2008.01.022","article-title":"Cyclohexane oxidation with dioxygen catalyzed by supported pyrazole rhenium complexes","volume":"285","author":"Mishra","year":"2008","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"3056","DOI":"10.1039\/c3cy00552f","article-title":"Homogeneous and Heterogenised New Gold C-Scorpionate Complexes as Catalysts for Cyclohexane Oxidation","volume":"3","author":"Martins","year":"2013","journal-title":"Catal. Sci. Technol."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"732","DOI":"10.1016\/j.ccr.2012.09.012","article-title":"Pyrazinecarboxylic acid and analogs: Highly efficient co-catalysts in the metal-complex-catalyzed oxidation of organic compounds","volume":"257","author":"Kirillov","year":"2013","journal-title":"Coord. Chem. Rev."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1021\/ic801753t","article-title":"Radical Formation in the [MeReO3]-Catalyzed Aqueous Peroxidative Oxidation of Alkanes: A Theoretical Mechanistic Study","volume":"48","author":"Kuznetsov","year":"2009","journal-title":"Inorg. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1016\/j.jcat.2009.08.006","article-title":"Mechanism of H2O2 Oxidations Catalyzed by Vanadate Anion or Oxovanadium(V) triethanolaminate (Vanadatrane) in Combination with Pyrazine-2-carboxylic acid (PCA): Kinetic and DFT studies","volume":"267","author":"Kirilova","year":"2009","journal-title":"J. Catal."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"1511","DOI":"10.1021\/cs200237m","article-title":"Participation of Oligovanadates in Alkane Oxidation with H2O2 Catalyzed by Vanadate Anion in Acidified Acetonitrile: Kinetic and DFT Studies","volume":"1","author":"Kirilova","year":"2011","journal-title":"ACS Catal."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"112","DOI":"10.1107\/S0108767307043930","article-title":"A short history of SHELX","volume":"A64","author":"Sheldrick","year":"2008","journal-title":"Acta Crystallogr. Sect. A"},{"key":"ref_62","unstructured":"(1997). Program for Crystal Structure Solution and Refinement, University of Goettingen."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/10\/19203\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T20:50:35Z","timestamp":1760215835000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/20\/10\/19203"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,10,21]]},"references-count":62,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2015,10]]}},"alternative-id":["molecules201019203"],"URL":"https:\/\/doi.org\/10.3390\/molecules201019203","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2015,10,21]]}}}