{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,15]],"date-time":"2025-12-15T19:46:58Z","timestamp":1765828018970,"version":"build-2065373602"},"reference-count":69,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2021,3,21]],"date-time":"2021-03-21T00:00:00Z","timestamp":1616284800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund","doi-asserted-by":"publisher","award":["KK.01.1.1.04.0013"],"award-info":[{"award-number":["KK.01.1.1.04.0013"]}],"id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Density functional theory calculations elucidated the precise reaction mechanism for the conversion of diphenylacetylenes into benzonitriles involving the cleavage of the triple C\u2261C bond, with N-iodosuccinimide (NIS) as an oxidant and trimethylsilyl azide (TMSN3) as a nitrogen donor. The reaction requires six steps with the activation barrier \u0394G\u2021 = 33.5 kcal mol\u22121 and a highly exergonic reaction free-energy \u0394GR = \u2212191.9 kcal mol\u22121 in MeCN. Reaction profiles agree with several experimental observations, offering evidence for the formation of molecular I2, interpreting the necessity to increase the temperature to finalize the reaction, and revealing thermodynamic aspects allowing higher yields for alkynes with para-electron-donating groups. In addition, the proposed mechanism indicates usefulness of this concept for both internal and terminal alkynes, eliminates the option to replace NIS by its Cl- or Br-analogues, and strongly promotes NaN3 as an alternative to TMSN3. Lastly, our results advise increasing the solvent polarity as another route to advance this metal-free strategy towards more efficient processes.<\/jats:p>","DOI":"10.3390\/ijms22063193","type":"journal-article","created":{"date-parts":[[2021,3,21]],"date-time":"2021-03-21T22:00:37Z","timestamp":1616364037000},"page":"3193","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Direct Metal-Free Transformation of Alkynes to Nitriles: Computational Evidence for the Precise Reaction Mechanism"],"prefix":"10.3390","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0731-1293","authenticated-orcid":false,"given":"Lucija","family":"Hok","sequence":"first","affiliation":[{"name":"Division of Organic Chemistry and Biochemistry, Ru\u0111er Bo\u0161kovi\u0107 Institute, Bijeni\u010dka Cesta 54, 10000 Zagreb, Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1779-4524","authenticated-orcid":false,"given":"Robert","family":"Vianello","sequence":"additional","affiliation":[{"name":"Division of Organic Chemistry and Biochemistry, Ru\u0111er Bo\u0161kovi\u0107 Institute, Bijeni\u010dka Cesta 54, 10000 Zagreb, Croatia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,3,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"122","DOI":"10.1038\/s41467-018-07985-2","article-title":"Iron-catalyzed carboazidation of alkenes and alkynes","volume":"10","author":"Xiong","year":"2019","journal-title":"Nat. Commun."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1016\/j.ccr.2019.02.011","article-title":"Noncovalent interactions in metal complex catalysis","volume":"387","author":"Mahmudov","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1016\/j.ccr.2019.01.024","article-title":"Recent advances in tridentate iron and cobalt complexes for alkene and alkyne hydrofunctionalizations","volume":"386","author":"Wen","year":"2019","journal-title":"Coord. Chem. Rev."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1593","DOI":"10.1021\/jacs.8b11039","article-title":"Direct Transformation of Terminal Alkynes into Amidines by a Silver-Catalyzed Four-Component Reaction","volume":"141","author":"Liu","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Trost, B.M., and Li, C.-J. (2014). Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations, Wiley.","DOI":"10.1002\/9783527677894"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"4563","DOI":"10.1002\/1521-3773(20021202)41:23<4563::AID-ANIE4563>3.0.CO;2-U","article-title":"Highly efficient AuI-catalyzed hydration of alkynes","volume":"41","author":"Mizushima","year":"2002","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"448","DOI":"10.1021\/ja809403e","article-title":"[(NHC)AuI]-Catalyzed Acid-Free Alkyne Hydration at Part-per-Million Catalyst Loadings","volume":"131","author":"Marion","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1021\/ja908911n","article-title":"Dioxygen Activation under Ambient Conditions: Cu-Catalyzed Oxidative Amidation-Diketonization of Terminal Alkynes Leading to \u03b1-Ketoamides","volume":"132","author":"Zhang","year":"2010","journal-title":"J. Am. Chem. Soc."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2142","DOI":"10.1021\/ol500592m","article-title":"Synthesis of \u03b1-Diketones from Alkylaryl- and Diarylalkynes Using Mercuric Salts","volume":"16","author":"Jung","year":"2014","journal-title":"Org. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2709","DOI":"10.1021\/jo5003517","article-title":"PIFA-Mediated Esterification Reaction of Alkynes with Alcohols via Oxidative Cleavage of Carbon Triple Bonds","volume":"79","author":"Jiang","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"11048","DOI":"10.1039\/C6OB01912A","article-title":"Transformations of alkynes to carboxylic acids and their derivatives via C\u2261C bond cleavage","volume":"14","author":"Kolle","year":"2016","journal-title":"Org. Biomol. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"500","DOI":"10.1002\/adsc.201500906","article-title":"Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C\u2261C Bond Cleavage under Aqueous Conditions","volume":"358","author":"Dighe","year":"2016","journal-title":"Adv. Synth. Catal."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"3285","DOI":"10.1039\/C5GC00528K","article-title":"Efficient bromination of olefins, alkynes, and ketones with dimethyl sulfoxide and hydrobromic acid","volume":"17","author":"Song","year":"2015","journal-title":"Green Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"936","DOI":"10.1016\/j.tetlet.2019.02.041","article-title":"Iodination of terminal alkynes using KI\/CuSO4\u2014A facile method with potential for radio-iodination","volume":"60","author":"Ferris","year":"2019","journal-title":"Tetrahedron Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"11332","DOI":"10.1021\/ja062610q","article-title":"Cleavage of a Carbon-Carbon Triple Bond via Gold-Catalyzed Cascade Cyclization\/Oxidative Cleavage Reactions of (Z)-Enynols with Molecular Oxygen","volume":"128","author":"Liu","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"164","DOI":"10.1039\/C7CC08792F","article-title":"Arylacetylenes as two-carbon synthons: Synthesis of eight-membered rings via C\u2261C bond cleavage","volume":"54","author":"Zhou","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3391","DOI":"10.1002\/adsc.201800592","article-title":"Oxidative Radical Cyclization of N-methyl-N-arylpropiolamide to Isatins via Cleavage of the Carbon-carbon Triple Bond","volume":"360","author":"Liao","year":"2018","journal-title":"Adv. Synth. Catal."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1021\/ar700133y","article-title":"Metal-organic cooperative catalysis in C-H and C-C bond activation and its concurrent recovery","volume":"41","author":"Park","year":"2008","journal-title":"Acc. Chem. Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1137","DOI":"10.1021\/ar400259e","article-title":"Direct approaches to nitriles via highly efficient nitrogenation strategy through C-H or C-C bond cleavage","volume":"47","author":"Wang","year":"2014","journal-title":"Acc. Chem. Res."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"860","DOI":"10.1021\/acs.orglett.6b00147","article-title":"Aryl Nitriles from Alkynes Using tert-Butyl Nitrite: Metal-Free Approach to C\u2261C Bond Cleavage","volume":"18","author":"Dutta","year":"2016","journal-title":"Org. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"6677","DOI":"10.1002\/anie.201300193","article-title":"Silver-catalyzed nitrogenation of alkynes: A direct approach to nitriles through C\u2261C bond cleavage","volume":"52","author":"Shen","year":"2013","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2571","DOI":"10.1021\/ol401311h","article-title":"Cleavage of Carbon-Carbon Triple Bond: Direct Transformation of Alkynes to Nitriles","volume":"15","author":"Okamoto","year":"2013","journal-title":"Org. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7142","DOI":"10.1039\/D0CY01692F","article-title":"Transition-metal-free trifluoromethylative difunctionalization of olefins and alkynes: Approaches and challenges ahead","volume":"10","author":"Keerthika","year":"2020","journal-title":"Catal. Sci. Technol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1002\/cssc.200900180","article-title":"Metal-free heterogeneous catalysis for sustainable chemistry","volume":"3","author":"Su","year":"2010","journal-title":"ChemSusChem"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3056","DOI":"10.1002\/ejoc.201600438","article-title":"Cleavage of the Carbon-Carbon Triple Bonds of Arylacetylenes for the Synthesis of Arylnitriles without a Metal Catalyst","volume":"2016","author":"Lin","year":"2016","journal-title":"Eur. J. Org. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"4245","DOI":"10.1038\/ncomms5245","article-title":"Facile scission of isonitrile carbon-nitrogen triple bond using a diborane(4) reagent","volume":"5","author":"Asakawa","year":"2014","journal-title":"Nat. Commun."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"213213","DOI":"10.1016\/j.ccr.2020.213213","article-title":"Metal-mediated cleavage of unsaturated C-C bonds","volume":"413","author":"Chan","year":"2020","journal-title":"Coord. Chem. Rev."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"350","DOI":"10.1002\/anie.201508347","article-title":"Splitting a Substrate into Three Parts: Gold-Catalyzed Nitrogenation of Alkynes by C-C and C\u2261C Bond Cleavage","volume":"55","author":"Qin","year":"2016","journal-title":"Angew. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5030","DOI":"10.1021\/ja8002217","article-title":"Palladium-Catalyzed Cleavage Reaction of Carbon-Carbon Triple Bond with Molecular Oxygen Promoted by Lewis Acid","volume":"130","author":"Wang","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1021\/cs300733s","article-title":"Palladium-Catalyzed C-C Triple Bond Cleavage: Efficient Synthesis of 4H-Benzo[d][1,3]oxazin-4-ones","volume":"3","author":"Liu","year":"2013","journal-title":"ACS Catal."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"6646","DOI":"10.1021\/ja034105o","article-title":"Carbon-Carbon Bond Cleavage of Diynes through the Hydroamination with Transition Metal Catalysts","volume":"125","author":"Shimada","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"9294","DOI":"10.1021\/ja036246w","article-title":"A New Ruthenium-Catalyzed Cleavage of a Carbon-Carbon Triple Bond: Efficient Transformation of Ethynyl Alcohol into Alkene and Carbon Monoxide","volume":"125","author":"Datta","year":"2003","journal-title":"J. Am. Chem. Soc."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"751","DOI":"10.1021\/ja0033537","article-title":"The C-C bond activation and skeletal rearrangement of cycloalkanone imine by Rh (I) catalysts","volume":"123","author":"Jun","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"6355","DOI":"10.1039\/C5SC02126J","article-title":"Copper-catalyzed direct transformation of simple alkynes to alkenyl nitriles via aerobic oxidative N-incorporation","volume":"6","author":"Huang","year":"2015","journal-title":"Chem. Sci."},{"key":"ref_35","doi-asserted-by":"crossref","unstructured":"Rappoport, Z. (1970). The Cyano Group, Wiley.","DOI":"10.1002\/9780470771242"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"32","DOI":"10.5923\/j.ajoc.20120202.06","article-title":"Utility of new activated nitriles in the synthesis of some new heterocyclic compounds","volume":"2","author":"Fadda","year":"2012","journal-title":"Am. J. Org. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1366","DOI":"10.1002\/slct.201601984","article-title":"Facile Transformation of Nitriles into Thioamides: Application to C-Glycosyl Nitrile Derivatives","volume":"2","author":"Ghosh","year":"2017","journal-title":"ChemistrySelect"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"7902","DOI":"10.1021\/jm100762r","article-title":"Nitrile-containing pharmaceuticals: Efficacious roles of the nitrile pharmacophore","volume":"53","author":"Fleming","year":"2010","journal-title":"J. Med. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1097\/COH.0000000000000471","article-title":"Doravirine: A review","volume":"13","author":"Colombier","year":"2018","journal-title":"Curr. Opin. HIV AIDS"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"303","DOI":"10.2147\/OTT.S182443","article-title":"Evaluating ivosidenib for the treatment of relapsed\/refractory AML: Design, development, and place in therapy","volume":"12","author":"Nassereddine","year":"2018","journal-title":"Onco. Targets Ther."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1080\/17512433.2019.1570846","article-title":"Lorlatinib for the treatment of anaplastic lymphoma kinase-positive non-small cell lung cancer","volume":"12","author":"Yang","year":"2019","journal-title":"Expert Rev. Clin. Pharmacol."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"563","DOI":"10.1021\/ar0000354","article-title":"Designer magnets containing cyanides and nitriles","volume":"34","author":"Miller","year":"2001","journal-title":"Acc. Chem. Res."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"9683","DOI":"10.1021\/ma201662h","article-title":"Flexible Solid Polymer Electrolytes Based on Nitrile Butadiene Rubber\/Poly (ethylene oxide) Interpenetrating Polymer Networks Containing Either LiTFSI or EMITFSI","volume":"44","author":"Goujon","year":"2011","journal-title":"Macromolecules"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2035","DOI":"10.1021\/cr020045d","article-title":"Unsaturated nitriles: Conjugate additions of carbon nucleophiles to a recalcitrant class of acceptors","volume":"103","author":"Fleming","year":"2003","journal-title":"Chem. Rev."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1633","DOI":"10.1002\/cber.18840170219","article-title":"Ueber die Ersetzung der Amidgruppe durch Chlor in den aromatischen Substanzen","volume":"17","author":"Sandmeyer","year":"1884","journal-title":"Chem. Ber."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1749","DOI":"10.1002\/cber.19190520840","article-title":"Das am Ringkohlenstoff gebundene Halogen und sein Ersatz durch andere Substituenten. I. Mitteilung: Ersatz des Halogens durch die Carboxylgruppe","volume":"52","author":"Rosenmund","year":"1919","journal-title":"Chem. Ber."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"779","DOI":"10.1021\/cr00080a006","article-title":"Cyanation of aromatic halides","volume":"87","author":"Ellis","year":"1987","journal-title":"Chem. Rev."},{"key":"ref_48","first-page":"23","article-title":"Palladium-Catalyzed Cyanation Reactions of Thiophene Halides","volume":"1","author":"Erker","year":"2004","journal-title":"Synthesis"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"5049","DOI":"10.1039\/c1cs15004a","article-title":"Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: Synthesis of benzonitriles","volume":"40","author":"Anbarasan","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"202","DOI":"10.1021\/ol5032359","article-title":"Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media","volume":"17","author":"Cohen","year":"2015","journal-title":"Org. Lett."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"825","DOI":"10.1039\/C4QO00158C","article-title":"Chopping unfunctionalized carbon-carbon bonds: A new paradigm for the synthesis of organonitriles","volume":"1","author":"Bisseret","year":"2014","journal-title":"Org. Chem. Front."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2328","DOI":"10.1038\/s41467-020-16201-z","article-title":"Prediction of organic homolytic bond dissociation enthalpies at near chemical accuracy with sub-second computational cost","volume":"11","author":"John","year":"2020","journal-title":"Nat. Commun."},{"key":"ref_53","doi-asserted-by":"crossref","unstructured":"Jasi\u0144ski, R., and Dresler, E. (2020). On the Question of Zwitterionic Intermediates in the [3 + 2] Cycloaddition Reactions: A Critical Review. Organics, 1.","DOI":"10.3390\/org1010005"},{"key":"ref_54","first-page":"1","article-title":"Flow Chemistry for Cycloaddition Reactions","volume":"13","year":"2020","journal-title":"ChemSusChem"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"9051","DOI":"10.1021\/acs.joc.0c00964","article-title":"Diastereocontrolled Formal Syntheses of (\u00b1)-Lepadiformines A, B, and C and the Divergent Synthesis of 2-epi-Lepadiformine C through Unexpected Double Consecutive Epimerizations","volume":"85","author":"Wu","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2828","DOI":"10.1002\/cssc.202000137","article-title":"Green Asymmetric Organocatalysis","volume":"13","year":"2020","journal-title":"ChemSusChem"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"5227","DOI":"10.1021\/cr800421c","article-title":"Recent Progress in Lewis Base Activation and Control of Stereoselectivity in the Additions of Trimethylsilyl Nucleophiles","volume":"108","author":"Gawronski","year":"2008","journal-title":"Chem. Rev."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"4814","DOI":"10.1021\/acs.jcim.9b00725","article-title":"A New Basis Set Exchange: An Open, Up-to-date Resource for the Molecular Sciences Community","volume":"59","author":"Pritchard","year":"2019","journal-title":"J. Chem. Inf. Model."},{"key":"ref_59","doi-asserted-by":"crossref","unstructured":"Pti\u010dek, L., Hok, L., Grb\u010di\u0107, P., Topi\u0107, F., Cetina, M., Rissanen, K., Paveli\u0107, S.K., Vianello, R., and Racan\u00e9, L. (2021). Amidino substituted 2-aminophenols: Biologically important building blocks for the amidino-functionalization of 2-substituted benzoxazoles. Org. Biomol. Chem.","DOI":"10.1039\/D1OB00235J"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"12471","DOI":"10.1021\/acs.joc.9b01944","article-title":"Transacylation in Ferrocenoyl-Purines. NMR and Computational Study of the Isomerization Mechanism","volume":"84","author":"Toma","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Cindri\u0107, M., Sovi\u0107, I., Mio\u010d, M., Hok, L., Bo\u010dek, I., Ro\u0161kari\u0107, P., Butkovi\u0107, K., Martin-Kleiner, I., Star\u010devi\u0107, K., and Vianello, R. (2019). Experimental and Computational Study of the Antioxidative Potential of Novel Nitro and Amino Substituted Benzimidazole\/Benzothiazole-2-Carboxamides with Antiproliferative Activity. Antioxidants, 8.","DOI":"10.3390\/antiox8100477"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"16445","DOI":"10.1021\/acs.inorgchem.9b02200","article-title":"Stereochemistry of Hexacoordinated Zn(II), Cu(II), Ni(II), and Co(II) Complexes with Iminodiacetamide Ligands","volume":"58","author":"Juraj","year":"2019","journal-title":"Inorg. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"9002","DOI":"10.1039\/D0DT01244K","article-title":"Copper(II) and Zinc(II) Complexes of Mono- and Bis-1,2,3-triazole substituted Heterocyclic Ligands","volume":"49","author":"Juraj","year":"2020","journal-title":"Dalton Transact."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1380","DOI":"10.1021\/acsomega.7b00130","article-title":"Kukushkin, Copper(I)-Catalyzed 1,3-Dipolar Cycloaddition of Ketonitrones to Dialkylcyanamides: A Step toward Sustainable Generation of 2,3-Dihydro-1,2,4-oxadiazoles","volume":"2","author":"Melekhova","year":"2017","journal-title":"ACS Omega"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"4039","DOI":"10.1021\/acs.inorgchem.5b00253","article-title":"Kukushkin, Bifunctional Reactivity of Amidoximes Observed upon Nucleophilic Addition to Metal-Activated Nitriles","volume":"54","author":"Bolotin","year":"2015","journal-title":"Inorg. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"3532","DOI":"10.1021\/acschemneuro.9b00147","article-title":"Computational Insight into the Mechanism of the Irreversible Inhibition of Monoamine Oxidase Enzymes by the Antiparkinsonian Propargylamine Inhibitors Rasagiline and Selegiline","volume":"10","author":"Vianello","year":"2019","journal-title":"ACS Chem. Neurosci."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2915","DOI":"10.1002\/chem.201605430","article-title":"What a difference a methyl group makes\u2014The selectivity of monoamine oxidase B towards histamine and N-methylhistamine","volume":"23","author":"Vianello","year":"2017","journal-title":"Chem. Eur. J."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"7211","DOI":"10.1021\/ja00544a007","article-title":"Natural hybrid orbitals","volume":"102","author":"Foster","year":"1980","journal-title":"J. Am. Chem. Soc."},{"key":"ref_69","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, Revision C.01, Gaussian, Inc."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/22\/6\/3193\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:38:50Z","timestamp":1760161130000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/22\/6\/3193"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,3,21]]},"references-count":69,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2021,3]]}},"alternative-id":["ijms22063193"],"URL":"https:\/\/doi.org\/10.3390\/ijms22063193","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2021,3,21]]}}}