{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T09:07:32Z","timestamp":1785920852185,"version":"3.56.0"},"reference-count":28,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2023,12,11]],"date-time":"2023-12-11T00:00:00Z","timestamp":1702252800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["21672111"],"award-info":[{"award-number":["21672111"]}]},{"name":"National Natural Science Foundation of China","award":["21472099"],"award-info":[{"award-number":["21472099"]}]},{"name":"National Natural Science Foundation of China","award":["21390400"],"award-info":[{"award-number":["21390400"]}]},{"name":"National Natural Science Foundation of China","award":["21102074"],"award-info":[{"award-number":["21102074"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Compounds with benzopyran as the core structure play an important role in the total synthesis of antioxidants, drugs, and natural products. Herein, the thermodynamic data of benzopyran compounds and their intermediates were measured and calculated by combining thermodynamics with kinetics. The mechanism of reactions between four benzopyran compounds and organic hydride acceptors was proven to be a one-step hydride transfer. The thermodynamic properties of these compounds and their corresponding intermediates were elucidated. The rationality and accuracy of the electrochemical measurement method were proved. Furthermore, the essential rule of unique structures being present between the C\u2013H bond and para-substituent constants on the benzene ring, as shown in previous studies, was investigated. A simultaneous correlation between thermodynamics and kinetics was found for the hydride transfer reaction, in which the reaction site is connected with the substituent through the benzene ring, a double bond, or a N atom. The likely reason for the correlation between thermodynamic and kinetic is that the benzene ring, double bond, or N atom have the role of transferring the electronic effect. This finding can be applied to the calculation of the activation energy of hydride self-exchange reactions, the prediction of kinetic isotope effects, and explorations of selective reduction processes of hydride transfer in such organic hydride compounds.<\/jats:p>","DOI":"10.3390\/molecules28248039","type":"journal-article","created":{"date-parts":[[2023,12,11]],"date-time":"2023-12-11T14:12:51Z","timestamp":1702303971000},"page":"8039","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["Essential Rule Derived from Thermodynamics and Kinetics Studies of Benzopyran Compounds"],"prefix":"10.3390","volume":"28","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4614-2242","authenticated-orcid":false,"given":"Baolong","family":"Chen","sequence":"first","affiliation":[{"name":"The State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin","family":"Hu","sequence":"additional","affiliation":[{"name":"School of Chemistry and Chemical Engineering, Nanchang University, Nanchang 330031, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2785-640X","authenticated-orcid":false,"given":"Xiaoqing","family":"Zhu","sequence":"additional","affiliation":[{"name":"The State Key Laboratory of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,12,11]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1080\/10408398.2021.1947772","article-title":"Enhancement of bioavailability and bioactivity of diet-derived flavonoids by application of nanotechnology: A review","volume":"63","author":"Teng","year":"2023","journal-title":"Crit. Rev. Food. Sci."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2178","DOI":"10.1080\/10408398.2021.1971945","article-title":"Citrus polyphenols and risk of type 2 diabetes: Evidence from mechanistic studies","volume":"63","author":"Visvanathan","year":"2023","journal-title":"Crit. Rev. Food. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"613","DOI":"10.1080\/14786419.2022.2065485","article-title":"Anti-arboviral activity and chemical characterization of hispidulin and ethanolic extracts from Millingtonia hortensis L.f. and Oroxylum indicum (L.) Kurz (Bignoniaceae)","volume":"37","author":"Valente","year":"2023","journal-title":"Nat. Prod. Res."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"44","DOI":"10.1080\/10286020.2022.2032677","article-title":"LSD1 inhibitors from the roots of Pueraria lobate","volume":"25","author":"Tian","year":"2023","journal-title":"J. Asian. Nat. Prod. Res."},{"key":"ref_5","doi-asserted-by":"crossref","unstructured":"Aboshabana, R., Elmansi, H., and El-Enany, N. (2023). Investigation of facile spectroscopic approaches for rapid calycosin determination in invitro biological samples and pharmaceuticals; application to the content uniformity of capsules. Spectrochim. Acta Part A Mol. Biomol. Spectrosc., 286.","DOI":"10.1016\/j.saa.2022.121904"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"111498","DOI":"10.1016\/j.plantsci.2022.111498","article-title":"Integration of transcriptomic and metabolomic analyses provides insights into response mechanisms to nitrogen and phosphorus deficiencies in soybean","volume":"326","author":"Metzger","year":"2023","journal-title":"Plant. Sci."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1078","DOI":"10.1080\/10408398.2021.1959295","article-title":"Halophytes as source of bioactive phenolic compounds and their potential applications","volume":"63","author":"Lopes","year":"2023","journal-title":"Crit. Rev. Food. Sci."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1007\/s13596-021-00607-1","article-title":"Ethnopharmacological survey of indigenous medicinal plants of Palampur, Himachal Pradesh in north-western Himalaya, India","volume":"23","author":"Arya","year":"2023","journal-title":"Adv. Tradit. Med."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"250","DOI":"10.1080\/10408347.2020.1797466","article-title":"Recent Progress in Small-Molecule Fluorescent Probes for Detecting Mercury Ions. Critical Reviews in Analytical Chemistry","volume":"52","author":"Yuan","year":"2022","journal-title":"Crit. Rev. Anal. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"515","DOI":"10.1080\/14786419.2020.1789632","article-title":"A new ceramide from the leaves of Lannea schimperi (Hochst. ex A. Rich.) Engl","volume":"36","author":"Nguemo","year":"2022","journal-title":"Nat. Prod. Res."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1007\/s10557-020-07091-w","article-title":"Effect of Statin Therapy on the Plasma Concentrations of Retinol, Alpha-Tocopherol and Coenzyme Q10 in Children with Familial Hypercholesterolemia","volume":"36","author":"Motkowski","year":"2022","journal-title":"Cardiovasc Drug. Ther."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"1942","DOI":"10.1080\/07391102.2020.1834455","article-title":"Molecular networking based dereplication of AChE inhibitory compounds from the medicinal plant Vincetoxicum funebre (Boiss. & Kotschy)","volume":"40","author":"Moridi","year":"2022","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_13","first-page":"5919","article-title":"Catalytic stereoselective benzylic C\u2013H functionalizations by oxidative C\u2013H activation and organocatalysis","volume":"39","author":"Fides","year":"2009","journal-title":"Chem. Commun."},{"key":"ref_14","first-page":"3167","article-title":"Enantioselective Synthesis of Chromanes by Iridium-Catalyzed Asymmetric Hydrogenation of 4H-Chromenes","volume":"20","author":"Carine","year":"2008","journal-title":"Synlett"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"4455","DOI":"10.1016\/S0040-4039(00)85924-9","article-title":"Oxythallation of flavenes. I: Direct conversion of flavenes to flavenes with thallium (III) nitrate","volume":"24","author":"Hatnm","year":"1983","journal-title":"Tetrahedron Lett."},{"key":"ref_16","first-page":"1831","article-title":"Reactions of Flav-2-enes and Flav-2-en-4-ones (Flavones)","volume":"8","author":"Geoffrey","year":"1983","journal-title":"J. Chem. Soc. Perkin Trans. I"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1021\/ar00029a010","article-title":"Bond energies in solution from electrode potentials and thermochemical cycles. A simplified and general approach","volume":"26","author":"Wayner","year":"1993","journal-title":"Acc. Chem. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"4774","DOI":"10.1021\/jo3005952","article-title":"Conversion and Origin of Normal and Abnormal Temperature Dependences of Kinetic Isotope Effect in Hydride Transfer Reactions","volume":"77","author":"Zhu","year":"2012","journal-title":"J. Org. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2501","DOI":"10.1021\/ja075523m","article-title":"Hydride, Hydrogen Atom, Proton, and Electron Transfer Driving Forces of Various Five-Membered Heterocyclic Organic Hydrides and Their Reaction Intermediates in Acetonitrile","volume":"130","author":"Zhu","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"6071","DOI":"10.1039\/c3ob40831k","article-title":"A Classical but New Kinetic Equation for Hydride Transfer Reactions","volume":"11","author":"Zhu","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"695","DOI":"10.1021\/ac00227a028","article-title":"Theory of square wave voltammetry for kinetic systems","volume":"53","author":"Osteryoung","year":"1981","journal-title":"Anal. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1779","DOI":"10.1021\/acs.jpca.5b10135","article-title":"Prediction of Kinetic Isotope Effects for Various Hydride Transfer Reactions Using a New Kinetic Model","volume":"120","author":"Shen","year":"2016","journal-title":"J. Phys. Chem. A"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4451","DOI":"10.1002\/1099-0690(200112)2001:23<4451::AID-EJOC4451>3.0.CO;2-F","article-title":"Kinetics of the Reactions of Flavylium Ions with \u03c0-Nucleophiles","volume":"2001","author":"Claudia","year":"2001","journal-title":"Eur. J. Org. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"872","DOI":"10.1021\/acsomega.7b01911","article-title":"Theoretical Prediction of Activation Free Energies of Various Hydride Self-Exchange Reactions in Acetonitrile at 298 K","volume":"3","author":"Li","year":"2018","journal-title":"ACS Omega"},{"key":"ref_25","first-page":"1035","article-title":"Synthesis, Molecular Docking Studies and Biological Evaluation of 3-Iminoaurones as Acetylcholinesterase and Butyrylcholinesterase Inhibitors","volume":"14","author":"Ehsan","year":"2017","journal-title":"Lett. Drug. Des. Discov."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"2736","DOI":"10.1016\/j.tet.2010.01.084","article-title":"Water as the reaction medium for multicomponent reactions basedon boronic acids","volume":"66","author":"Nuno","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1205","DOI":"10.1002\/jhet.5570240453","article-title":"Tandem Arylation-Reduction of Acyl Heterocycles Convenient Synthesis of Benzyl [1,2]","volume":"24","author":"Stan","year":"1987","journal-title":"J. Heterocyclic. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"9383","DOI":"10.1021\/jo7015604","article-title":"TFA-Mediated Tandem Friedel-Crafts Alkylation\/Cyclization\/Hydrogen Transfer Process for the Synthesis of Flavylium Compounds","volume":"72","author":"Wu","year":"2007","journal-title":"J. Org. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/24\/8039\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T21:36:42Z","timestamp":1760132202000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/28\/24\/8039"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,12,11]]},"references-count":28,"journal-issue":{"issue":"24","published-online":{"date-parts":[[2023,12]]}},"alternative-id":["molecules28248039"],"URL":"https:\/\/doi.org\/10.3390\/molecules28248039","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,12,11]]}}}