异黄酮的抗氧化作用及其在水溶液中的去质子化形式的热化学:氢或电子转移?

IF 0.9 Q4 CHEMISTRY, MULTIDISCIPLINARY
Monika Biela, A. Kleinová, E. Klein
{"title":"异黄酮的抗氧化作用及其在水溶液中的去质子化形式的热化学:氢或电子转移?","authors":"Monika Biela, A. Kleinová, E. Klein","doi":"10.2478/acs-2022-0004","DOIUrl":null,"url":null,"abstract":"Abstract Isoflavones possessing several weak acidic hydroxyl groups can undergo successive deprotonations in aqueous solutions. Therefore, their antioxidant properties cannot be ascribed only to the neutral forms but also to corresponding phenoxide anions. It was already confirmed that isoflavones prefer the formation of dianions in aqueous solution. For eight isoflavones and their preferred (poly)deprotonated forms, thermochemistry of hydrogen atom transfer and electron abstraction was studied in terms of corresponding reaction enthalpies, i.e., O—H bond dissociation enthalpies and ionization potentials. Our results clearly indicate that the increase in negative charge causes significant drop in ionization potential and bond dissociation enthalpy. On the other hand, proton affinities show the opposite trend. Thus, it is unfeasible to find a generally valid trend for dianions — corresponding reaction enthalpies strongly depend on the structure of isoflavone, especially on the number/positions of OH groups.","PeriodicalId":7088,"journal":{"name":"Acta Chimica Slovaca","volume":null,"pages":null},"PeriodicalIF":0.9000,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Thermochemistry of antioxidant action of isoflavones and their deprotonated forms in aqueous solution: hydrogen or electron transfer?\",\"authors\":\"Monika Biela, A. Kleinová, E. Klein\",\"doi\":\"10.2478/acs-2022-0004\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Abstract Isoflavones possessing several weak acidic hydroxyl groups can undergo successive deprotonations in aqueous solutions. Therefore, their antioxidant properties cannot be ascribed only to the neutral forms but also to corresponding phenoxide anions. It was already confirmed that isoflavones prefer the formation of dianions in aqueous solution. For eight isoflavones and their preferred (poly)deprotonated forms, thermochemistry of hydrogen atom transfer and electron abstraction was studied in terms of corresponding reaction enthalpies, i.e., O—H bond dissociation enthalpies and ionization potentials. Our results clearly indicate that the increase in negative charge causes significant drop in ionization potential and bond dissociation enthalpy. On the other hand, proton affinities show the opposite trend. Thus, it is unfeasible to find a generally valid trend for dianions — corresponding reaction enthalpies strongly depend on the structure of isoflavone, especially on the number/positions of OH groups.\",\"PeriodicalId\":7088,\"journal\":{\"name\":\"Acta Chimica Slovaca\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.9000,\"publicationDate\":\"2022-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta Chimica Slovaca\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.2478/acs-2022-0004\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Chimica Slovaca","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2478/acs-2022-0004","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

摘要

具有几个弱酸性羟基的异黄酮在水溶液中可发生连续的去质子化。因此,它们的抗氧化性能不能仅仅归因于中性形式,也归因于相应的苯氧阴离子。已经证实异黄酮在水溶液中倾向于形成阴离子。对8种异黄酮及其优选的(聚)去质子形式,根据相应的反应焓,即O-H键解离焓和电离势,研究了氢原子转移和电子抽离的热化学性质。我们的结果清楚地表明,负电荷的增加导致电离势和键解离焓的显著下降。另一方面,质子的亲合力则呈现相反的趋势。因此,寻找一个普遍有效的趋势是不可能的,相应的反应焓强烈地依赖于异黄酮的结构,特别是OH基团的数目/位置。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Thermochemistry of antioxidant action of isoflavones and their deprotonated forms in aqueous solution: hydrogen or electron transfer?
Abstract Isoflavones possessing several weak acidic hydroxyl groups can undergo successive deprotonations in aqueous solutions. Therefore, their antioxidant properties cannot be ascribed only to the neutral forms but also to corresponding phenoxide anions. It was already confirmed that isoflavones prefer the formation of dianions in aqueous solution. For eight isoflavones and their preferred (poly)deprotonated forms, thermochemistry of hydrogen atom transfer and electron abstraction was studied in terms of corresponding reaction enthalpies, i.e., O—H bond dissociation enthalpies and ionization potentials. Our results clearly indicate that the increase in negative charge causes significant drop in ionization potential and bond dissociation enthalpy. On the other hand, proton affinities show the opposite trend. Thus, it is unfeasible to find a generally valid trend for dianions — corresponding reaction enthalpies strongly depend on the structure of isoflavone, especially on the number/positions of OH groups.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Acta Chimica Slovaca
Acta Chimica Slovaca CHEMISTRY, MULTIDISCIPLINARY-
自引率
12.50%
发文量
11
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信