{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:59:07Z","timestamp":1787029147293,"version":"build-2736575974"},"reference-count":86,"publisher":"MDPI AG","issue":"7","license":[{"start":{"date-parts":[[2025,3,21]],"date-time":"2025-03-21T00:00:00Z","timestamp":1742515200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Universit\u00e0 degli Studi di Padova"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Phenolic compounds are important antioxidants with great ROS scavenging potential and the presence of the hydroxyl groups is fundamental for this chemical activity. Therefore, changing the chalcogen atom (oxygen) with any of its siblings of group 16 (sulfur, selenium and tellurium) may affect the reactivity of these compounds. In this work, the ROS scavenging activity and mechanism of phenyl chalcogenols was evaluated in silico, unravelling better performance with heavier chalcogens, both thermodynamically and kinetically. Furthermore, a scavenging mechanism switch is reported, moving from Concerted Proton Electron Transfer (CPET) in phenols to Hydrogen Atom Transfer (HAT) in the other phenyl chalcogenols. Both kinetic trends and mechanistic features are rationalized in the framework of Activation Strain Analysis (ASA). Lastly, the role of aromaticity is evidenced by analyzing the differences between the phenol\/phenoxyl and methanol\/methoxyl self-exchange reactions, as well as between the corresponding processes with the other chalcogens.<\/jats:p>","DOI":"10.3390\/molecules30071408","type":"journal-article","created":{"date-parts":[[2025,3,24]],"date-time":"2025-03-24T04:48:18Z","timestamp":1742791698000},"page":"1408","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":9,"title":["The Role of Chalcogen in the ROS Scavenging Mechanism of Model Phenyl Compounds"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0961-0764","authenticated-orcid":false,"given":"Davide","family":"Zeppilli","sequence":"first","affiliation":[{"name":"Dipartimento di Scienze Chimiche, Universit\u00e0 degli Studi di Padova, Via Marzolo 1, 35131 Padova, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Veronica","family":"Pedergnana","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche, Universit\u00e0 degli Studi di Padova, Via Marzolo 1, 35131 Padova, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0009-1249-5630","authenticated-orcid":false,"given":"Matteo","family":"Filippi","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche, Universit\u00e0 degli Studi di Padova, Via Marzolo 1, 35131 Padova, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1673-5111","authenticated-orcid":false,"given":"Laura","family":"Orian","sequence":"additional","affiliation":[{"name":"Dipartimento di Scienze Chimiche, Universit\u00e0 degli Studi di Padova, Via Marzolo 1, 35131 Padova, Italy"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,3,21]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1016\/j.redox.2015.01.002","article-title":"Oxidative Stress: A Concept in Redox Biology and Medicine","volume":"4","author":"Sies","year":"2015","journal-title":"Redox Biol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"715","DOI":"10.1146\/annurev-biochem-061516-045037","article-title":"Oxidative Stress","volume":"86","author":"Sies","year":"2017","journal-title":"Annu. Rev. Biochem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1038\/nrd1330","article-title":"Neurodegenerative Diseases and Oxidative Stress","volume":"3","author":"Barnham","year":"2004","journal-title":"Nat. Rev. Drug. Discov."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Dubois-Deruy, E., Peugnet, V., Turkieh, A., and Pinet, F. (2020). Oxidative Stress in Cardiovascular Diseases. Antioxidants, 9.","DOI":"10.3390\/antiox9090864"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"4771","DOI":"10.2174\/1381612825666190215121712","article-title":"Oxidative Stress and Cancer","volume":"24","author":"Klaunig","year":"2019","journal-title":"Curr. Pharm. Des."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"567","DOI":"10.2147\/NDT.S44282","article-title":"Mitochondrial Dysfunction, Oxidative Stress, and Major Depressive Disorder","volume":"9","author":"Tobe","year":"2013","journal-title":"Neuropsychiatr. Dis. Treat."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"185","DOI":"10.1097\/YCO.0000000000000054","article-title":"Oxidative Stress and Schizophrenia","volume":"27","author":"Emiliani","year":"2014","journal-title":"Curr. Opin. Psychiatry"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"413","DOI":"10.1080\/10715762.2017.1315114","article-title":"In Vivo ROS Production and Use of Oxidative Stress-Derived Biomarkers to Detect the Onset of Diseases Such as Alzheimer\u2019s Disease, Parkinson\u2019s Disease, and Diabetes","volume":"51","author":"Umeno","year":"2017","journal-title":"Free Radic. Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1482","DOI":"10.3109\/10715762.2012.727991","article-title":"Oxidative Stress as a Potential Biomarker for Determining Disease Activity in Patients with Rheumatoid Arthritis","volume":"46","author":"Kundu","year":"2012","journal-title":"Free Radic. Res."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"411","DOI":"10.1111\/jpi.12362","article-title":"Apoptosis Signaling Pathways in Osteoarthritis and Possible Protective Role of Melatonin","volume":"61","author":"Hosseinzadeh","year":"2016","journal-title":"J. Pineal Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1089\/ars.2016.6755","article-title":"The Role of Oxidative Stress and Hypoxia in Pancreatic Beta-Cell Dysfunction in Diabetes Mellitus","volume":"26","author":"Gerber","year":"2017","journal-title":"Antioxid. Redox Signal."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Juan, C.A., P\u00e9rez de la Lastra, J.M., Plou, F.J., and P\u00e9rez-Lebe\u00f1a, E. (2021). The Chemistry of Reactive Oxygen Species (ROS) Revisited: Outlining Their Role in Biological Macromolecules (DNA, Lipids and Proteins) and Induced Pathologies. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22094642"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"219","DOI":"10.1016\/0891-5849(88)90043-3","article-title":"Why Is the Hydroxyl Radical the Only Radical That Commonly Adds to DNA? Hypothesis: It Has a Rare Combination of High Electrophilicity, High Thermochemical Reactivity, and a Mode of Production That Can Occur near DNA","volume":"4","author":"Pryor","year":"1988","journal-title":"Free Radic. Biol. Med."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/qua.25665","article-title":"Computational Strategies for Predicting Free Radical Scavengers\u2019 Protection against Oxidative Stress: Where Are We and What Might Follow?","volume":"119","author":"Galano","year":"2019","journal-title":"Int. J. Quantum Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"657","DOI":"10.1146\/annurev.ph.48.030186.003301","article-title":"Oxy-Radicals and Related Species: Their Formation, Lifetimes, and Reactions","volume":"48","author":"Pryor","year":"1986","journal-title":"Annu. Rev. Physiol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1365","DOI":"10.1093\/carcin\/8.10.1365","article-title":"Peroxyl Free Radicals: Potential Mediators of Tumor Initiation and Promotion","volume":"8","author":"Marnett","year":"1987","journal-title":"Carcinogenesis"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"235","DOI":"10.1016\/0891-5849(94)90079-5","article-title":"Importance of SE-Glutathione Peroxidase, Catalase, and CU\/ZN-SOD for Cell Survival against Oxidative Stress","volume":"17","author":"Michiels","year":"1994","journal-title":"Free Radic. Biol. Med."},{"key":"ref_18","first-page":"95","article-title":"Glutathione Peroxidase: Fact and Fiction","volume":"65","year":"1978","journal-title":"Ciba Found. Symp."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Orian, L., and Floh\u00e9, L. (2021). Selenium-Catalyzed Reduction of Hydroperoxides in Chemistry and Biology. Antioxidants, 10.","DOI":"10.3390\/antiox10101560"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"113","DOI":"10.1016\/j.freeradbiomed.2022.05.003","article-title":"The Glutathione Peroxidase Family: Discoveries and Mechanism","volume":"187","author":"Toppo","year":"2022","journal-title":"Free Radic. Biol. Med."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Eleutherio, E.C.A., Silva Magalh\u00e3es, R.S., de Ara\u00fajo Brasil, A., Monteiro Neto, J.R., and de Holanda Paranhos, L. (2021). SOD1, More than Just an Antioxidant. Arch. Biochem. Biophys., 697.","DOI":"10.1016\/j.abb.2020.108701"},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Narayanaperumal, S., Alberto, E.E., de Andrade, F.M., Lenard\u00e3o, E.J., Taube, P.S., and Braga, A.L. (2009). Ionic Liquid: An Efficient and Recyclable Medium for Synthesis of Unsymmetrical Diorganyl Selenides Promoted by InI. Org. Biomol. Chem., 7.","DOI":"10.1039\/b910699e"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"e12514","DOI":"10.1111\/jpi.12514","article-title":"Melatonin and Its Metabolites vs. Oxidative Stress: From Individual Actions to Collective Protection","volume":"65","author":"Galano","year":"2018","journal-title":"J. Pineal Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1111\/j.1600-079X.2011.00916.x","article-title":"Melatonin as a Natural Ally against Oxidative Stress: A Physicochemical Examination","volume":"51","author":"Galano","year":"2011","journal-title":"J. Pineal Res."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1111\/jpi.12196","article-title":"Melatonin and Its Metabolites as Copper Chelating Agents and Their Role in Inhibiting Oxidative Stress: A Physicochemical Analysis","volume":"58","author":"Galano","year":"2015","journal-title":"J. Pineal Res."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1657","DOI":"10.1002\/fsn3.3217","article-title":"Natural Antioxidants from Some Fruits, Seeds, Foods, Natural Products, and Associated Health Benefits: An Update","volume":"11","author":"Rahaman","year":"2023","journal-title":"Food Sci. Nutr."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1163","DOI":"10.2174\/0929867043365323","article-title":"Oxidative Stress and Cell Signalling","volume":"11","author":"Poli","year":"2004","journal-title":"Curr. Med. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1093\/mp\/ssp106","article-title":"Phenylpropanoid Biosynthesis","volume":"3","author":"Vogt","year":"2010","journal-title":"Mol. Plant"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"134677","DOI":"10.1016\/j.foodchem.2022.134677","article-title":"The Mechanistic Insights into the Role of PH and Solvent on Antiradical and Prooxidant Properties of Polyphenols\u2014Nine Compounds Case Study","volume":"407","author":"Spiegel","year":"2023","journal-title":"Food Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1673","DOI":"10.1211\/jpp.59.12.0010","article-title":"Antioxidant Properties of Phenols","volume":"59","author":"Foti","year":"2007","journal-title":"J. Pharm. Pharmacol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1379","DOI":"10.1002\/ptr.5643","article-title":"Prooxidant Activity of Polyphenols, Flavonoids, Anthocyanins and Carotenoids: Updated Review of Mechanisms and Catalyzing Metals","volume":"30","author":"Eghbaliferiz","year":"2016","journal-title":"Phytother. Res."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"112528","DOI":"10.1016\/j.phytochem.2020.112528","article-title":"Antioxidant Action of Deprotonated Flavonoids: Thermodynamics of Sequential Proton-Loss Electron-Transfer","volume":"180","author":"Biela","year":"2020","journal-title":"Phytochemistry"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1016\/j.comptc.2015.09.003","article-title":"The 2H+\/2e\u2212 Free Radical Scavenging Mechanisms of Uric Acid: Thermodynamics of NH Bond Cleavage","volume":"1077","year":"2016","journal-title":"Comput. Theor. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"11913","DOI":"10.1002\/anie.201805511","article-title":"CPCET versus HAT: A Direct Theoretical Method for Distinguishing X\u2013H Bond-Activation Mechanisms","volume":"57","author":"Klein","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"17090","DOI":"10.1021\/ja408073m","article-title":"Dichotomous Hydrogen Atom Transfer vs. Proton-Coupled Electron Transfer During Activation of X\u2013H Bonds (X = C, N, O) by Nonheme Iron\u2013Oxo Complexes of Variable Basicity","volume":"135","author":"Usharani","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1146\/annurev.physchem.55.091602.094446","article-title":"Proton-Coupled Electron Transfer: A Reaction Chemist\u2019s View","volume":"55","author":"Mayer","year":"2004","journal-title":"Annu. Rev. Phys. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1089\/ars.2017.7115","article-title":"GPx4, Lipid Peroxidation, and Cell Death: Discoveries, Rediscoveries, and Open Issues","volume":"29","author":"Maiorino","year":"2018","journal-title":"Antioxid. Redox Signal."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"907","DOI":"10.2174\/1389203720666190206130003","article-title":"Glutathione, an Antioxidant Tripeptide: Dual Roles in Carcinogenesis and Chemoprevention","volume":"20","author":"Narayanankutty","year":"2019","journal-title":"Curr. Protein Pept. Sci."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"11864","DOI":"10.1021\/bi050815q","article-title":"Elucidation of the Mechanism of Selenoprotein Glutathione Peroxidase (GPx)-Catalyzed Hydrogen Peroxide Reduction by Two Glutathione Molecules: A Density Functional Study","volume":"44","author":"Prabhakar","year":"2005","journal-title":"Biochemistry"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.freeradbiomed.2022.06.227","article-title":"A White Paper on Phospholipid Hydroperoxide Glutathione Peroxidase (GPx4) Forty Years Later","volume":"188","author":"Ursini","year":"2022","journal-title":"Free Radic. Biol. Med."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"12075","DOI":"10.1021\/ic201603v","article-title":"Modeling the Mechanism of the Glutathione Peroxidase Mimic Ebselen","volume":"50","author":"Antony","year":"2011","journal-title":"Inorg. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3680","DOI":"10.1002\/ejic.201300279","article-title":"Modeling the Glutathione Peroxidase-Like Activity of a Cyclic Seleninate by DFT and Solvent-Assisted Proton Exchange","volume":"2013","author":"Bayse","year":"2013","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"e202403003","DOI":"10.1002\/chem.202403003","article-title":"50 Years of Organoselenium Chemistry, Biochemistry and Reactivity: Mechanistic Understanding, Successful and Controversial Stories","volume":"30","author":"Madabeni","year":"2024","journal-title":"Chem. Eur. J."},{"key":"ref_44","unstructured":"Alvarez, B., Comini, M.A., Salinas, G., and Trujillo, M. (2022). Therapeutic Applications of Low-Molecular-Weight Thiols and Selenocompounds. Redox Chemistry and Biology of Thiols, Elsevier."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"17288","DOI":"10.1021\/acs.inorgchem.3c02568","article-title":"Role of Group 12 Metals in the Reduction of H2O2 by Santi\u2019s Reagent: A Computational Mechanistic Investigation","volume":"62","author":"Zeppilli","year":"2023","journal-title":"Inorg. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"18583","DOI":"10.1039\/D0RA03509B","article-title":"Fluoxetine Scaffold to Design Tandem Molecular Antioxidants and Green Catalysts","volume":"10","author":"Ribaudo","year":"2020","journal-title":"RSC Adv."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"8314","DOI":"10.1021\/acsomega.1c05567","article-title":"ROS-Scavenging Selenofluoxetine Derivatives Inhibit In Vivo Serotonin Reuptake","volume":"7","author":"Ribaudo","year":"2022","journal-title":"ACS Omega"},{"key":"ref_48","doi-asserted-by":"crossref","unstructured":"Zeppilli, D., Aldinio-Colbachini, A., Ribaudo, G., Tubaro, C., Dalla Tiezza, M., Bortoli, M., Zagotto, G., and Orian, L. (2023). Antioxidant Chimeric Molecules: Are Chemical Motifs Additive? The Case of a Selenium-Based Ligand. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms241411797"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"3763","DOI":"10.1002\/cmdc.202100546","article-title":"Radical Scavenging Potential of the Phenothiazine Scaffold: A Computational Analysis","volume":"16","author":"Hamlin","year":"2021","journal-title":"ChemMedChem"},{"key":"ref_50","doi-asserted-by":"crossref","unstructured":"Mangiavacchi, F., Botwina, P., Menichetti, E., Bagnoli, L., Rosati, O., Marini, F., Fonseca, S.F., Abenante, L., Alves, D., and Dabrowska, A. (2021). Seleno-Functionalization of Quercetin Improves the Non-Covalent Inhibition of Mpro and Its Antiviral Activity in Cells against SARS-CoV-2. Int. J. Mol. Sci., 22.","DOI":"10.3390\/ijms22137048"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"857","DOI":"10.1080\/004982500433282","article-title":"Sulphation of Resveratrol, a Natural Compound Present in Wine, and Its Inhibition by Natural Flavonoids","volume":"30","author":"Pietrabissa","year":"2000","journal-title":"Xenobiotica"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"6312","DOI":"10.1039\/D5CP00690B","article-title":"Concerted Proton Electron Transfer or Hydrogen Atom Transfer? An Unequivocal Strategy to Discriminate These Mechanisms in Model Systems","volume":"27","author":"Zeppilli","year":"2025","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1111\/j.1749-6632.2002.tb02905.x","article-title":"Chemistry of the Antioxidant Effect of Polyphenols","volume":"957","author":"Bors","year":"2002","journal-title":"Ann. N. Y. Acad. Sci."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2082","DOI":"10.1021\/jp3116319","article-title":"Free Radical Scavenging by Natural Polyphenols: Atom versus Electron Transfer","volume":"117","author":"Lemaur","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"S1703","DOI":"10.1016\/j.arabjc.2013.06.019","article-title":"Effect of Donor and Acceptor Groups on Radical Scavenging Activity of Phenol by Density Functional Theory","volume":"10","author":"Irfan","year":"2017","journal-title":"Arab. J. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","unstructured":"Platzer, M., Kiese, S., Tybussek, T., Herfellner, T., Schneider, F., Schweiggert-Weisz, U., and Eisner, P. (2022). Radical Scavenging Mechanisms of Phenolic Compounds: A Quantitative Structure-Property Relationship (QSPR) Study. Front. Nutr., 9.","DOI":"10.3389\/fnut.2022.882458"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"25974","DOI":"10.1021\/acsomega.2c03291","article-title":"Natural Antioxidant Compounds as Potential Pharmaceutical Tools against Neurodegenerative Diseases","volume":"7","author":"Marino","year":"2022","journal-title":"ACS Omega"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"221","DOI":"10.1111\/j.1541-4337.2011.00156.x","article-title":"Natural Antioxidants: Sources, Compounds, Mechanisms of Action, and Potential Applications","volume":"10","author":"Brewer","year":"2011","journal-title":"Compr. Rev. Food Sci. Food Saf."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"27986","DOI":"10.1039\/C4RA13315C","article-title":"Free Radicals, Natural Antioxidants, and Their Reaction Mechanisms","volume":"5","author":"Nimse","year":"2015","journal-title":"RSC Adv."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"64","DOI":"10.1016\/j.comptc.2016.01.014","article-title":"Theoretical Study of the Substituent Effect on the Hydrogen Atom Transfer Mechanism of Meta- and Para-Substituted Benzenetellurols","volume":"1079","author":"Poliak","year":"2016","journal-title":"Comput. Theor. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1315","DOI":"10.1002\/cphc.201701363","article-title":"Nucleophilic Substitution (SN2): Dependence on Nucleophile, Leaving Group, Central Atom, Substituents, and Solvent","volume":"19","author":"Hamlin","year":"2018","journal-title":"ChemPhysChem"},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"11142","DOI":"10.1021\/ja012732c","article-title":"Proton-Coupled Electron Transfer versus Hydrogen Atom Transfer in Benzyl\/Toluene, Methoxyl\/Methanol, and Phenoxyl\/Phenol Self-Exchange Reactions","volume":"124","author":"Mayer","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"6199","DOI":"10.1021\/ja068090g","article-title":"Lone Pair\u2212\u03c0 and \u03a0\u2212\u03c0 Interactions Play an Important Role in Proton-Coupled Electron Transfer Reactions","volume":"129","author":"DiLabio","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"2367","DOI":"10.1021\/jp111210c","article-title":"Proton-Coupled Electron Transfer versus Hydrogen Atom Transfer: Generation of Charge-Localized Diabatic States","volume":"115","author":"Sirjoosingh","year":"2011","journal-title":"J. Phys. Chem. A"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"222","DOI":"10.1021\/ar0682029","article-title":"Solvent Effects on the Rates and Mechanisms of Reaction of Phenols with Free Radicals","volume":"40","author":"Litwinienko","year":"2007","journal-title":"Acc. Chem. Res."},{"key":"ref_66","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 B.01, Gaussian, Inc."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1007\/s00214-007-0310-x","article-title":"The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals","volume":"120","author":"Zhao","year":"2008","journal-title":"Theor. Chem. Acc."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"104103","DOI":"10.1063\/1.1856451","article-title":"All-Electron and Relativistic Pseudopotential Studies for the Group 1 Element Polarizabilities from K to Element 119","volume":"122","author":"Lim","year":"2005","journal-title":"J. Chem. Phys."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"2721","DOI":"10.1021\/acs.jchemed.2c00443","article-title":"Not That DDT: A Databank of Dynamics Trajectories for Organic Reactions","volume":"99","author":"Zhang","year":"2022","journal-title":"J. Chem. Educ."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"4834","DOI":"10.1021\/ct400687b","article-title":"Intrinsic Atomic Orbitals: An Unbiased Bridge between Quantum Theory and Chemical Concepts","volume":"9","author":"Knizia","year":"2013","journal-title":"J. Chem. Theory Comput."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"5518","DOI":"10.1002\/anie.201410637","article-title":"Electron Flow in Reaction Mechanisms\u2014Revealed from First Principles","volume":"54","author":"Knizia","year":"2015","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"2430","DOI":"10.1002\/jcc.23409","article-title":"A Computational Methodology for Accurate Predictions of Rate Constants in Solution: Application to the Assessment of Primary Antioxidant Activity","volume":"34","author":"Galano","year":"2013","journal-title":"J. Comput. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"324","DOI":"10.1002\/wcms.1221","article-title":"The Activation Strain Model and Molecular Orbital Theory","volume":"5","author":"Wolters","year":"2015","journal-title":"Wiley Interdiscip. Rev. Comput. Mol. Sci."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"10070","DOI":"10.1002\/anie.201701486","article-title":"Analyzing Reaction Rates with the Distortion\/Interaction-Activation Strain Model","volume":"56","author":"Bickelhaupt","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/9780470125922.ch1","article-title":"Kohn-Sham Density Functional Theory: Predicting and Understanding Chemistry","volume":"Volume 15","author":"Lipkowitz","year":"2000","journal-title":"Reviews in Computational Chemistry"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1038\/s41596-019-0265-0","article-title":"Understanding Chemical Reactivity Using the Activation Strain Model","volume":"15","author":"Vermeeren","year":"2020","journal-title":"Nat. Protoc."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"312","DOI":"10.1002\/jcc.20786","article-title":"PyFrag\u2014Streamlining Your Reaction Path Analysis","volume":"29","author":"Guerra","year":"2008","journal-title":"J. Comput. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"931","DOI":"10.1002\/jcc.1056","article-title":"Chemistry with ADF","volume":"22","author":"Bickelhaupt","year":"2001","journal-title":"J. Comput. Chem."},{"key":"ref_79","unstructured":"(2025, January 10). ADF2019, AMS2020, SCM. Theoretical Chemistry. Available online: https:\/\/www.scm.com\/."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"9783","DOI":"10.1063\/1.467943","article-title":"Relativistic Total Energy Using Regular Approximations","volume":"101","author":"Baerends","year":"1994","journal-title":"J. Chem. Phys."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"1672","DOI":"10.1002\/jcc.24383","article-title":"Insights on Selenium and Tellurium Diaryldichalcogenides: A Benchmark DFT Study","volume":"37","author":"Zaccaria","year":"2016","journal-title":"J. Comput. Chem."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"e202400728","DOI":"10.1002\/cphc.202400728","article-title":"Radical Addition Reactions: Hierarchical Ab Initio Benchmark and DFT Performance Study","volume":"26","author":"Hordijk","year":"2025","journal-title":"ChemPhysChem"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"e202200755","DOI":"10.1002\/chem.202200755","article-title":"How the Chalcogen Atom Size Dictates the Hydrogen-Bond Donor Capability of Carboxamides, Thioamides, and Selenoamides","volume":"28","author":"Nieuwland","year":"2022","journal-title":"Chem. Eur. J."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"2224","DOI":"10.1021\/j100007a062","article-title":"Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena","volume":"99","author":"Klamt","year":"1995","journal-title":"J. Phys. Chem."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"2639","DOI":"10.1021\/acs.jcim.2c00104","article-title":"Current Trends in Computational Quantum Chemistry Studies on Antioxidant Radical Scavenging Activity","volume":"62","author":"Spiegel","year":"2022","journal-title":"J. Chem. Inf. Model."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"21856","DOI":"10.1021\/acs.inorgchem.4c02534","article-title":"Radical Scavenging and Anti-Ferroptotic Molecular Mechanism of Olanzapine: Insight from a Computational Analysis","volume":"63","author":"Zeppilli","year":"2024","journal-title":"Inorg. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/7\/1408\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T16:58:15Z","timestamp":1760029095000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/7\/1408"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,3,21]]},"references-count":86,"journal-issue":{"issue":"7","published-online":{"date-parts":[[2025,4]]}},"alternative-id":["molecules30071408"],"URL":"https:\/\/doi.org\/10.3390\/molecules30071408","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,3,21]]}}}