• 主题
高级搜索  >
历史搜索 清空历史
首页> 外文期刊>RSC Advances >Correlating experimental electrochemistry and theoretical calculations in 2 '-hydroxy chalcones: the role of the intramolecular hydrogen bond
【24h】

Correlating experimental electrochemistry and theoretical calculations in 2 '-hydroxy chalcones: the role of the intramolecular hydrogen bond

机译：在2'-羟基查耳酮中关联实验电化学和理论计算：分子内氢键的作用

获取原文
获取原文并翻译 | 示例
           
页面导航
  • 摘要
  • 著录项
  • 相似文献
  • 相关主题

摘要

In this work we present a study on the molecular structure and electrochemical behavior of a series of methoxylated 2'-hydroxychalcones, whose antitumor activity has been previously described. Cyclic voltammetry was used to quantitatively characterize the formation and stability of the anion radicals. The molecular structure of the neutral compounds and their anion radicals, particularly the intramolecular hydrogen bonds (IHB), were investigated through density functional theory (DFT) calculations. Geometrical and frontier orbital changes in the anion, relative to the neutral species, were examined and the adiabatic and vertical electron affinities (AEA, VEA) as well as vertical detachment energy (VDE) were calculated. Natural bond orbital (NBO) analysis was used to obtain insights into the electronic characteristics of the IHB and the results were correlated with H-1-NMR chemical shifts. A direct relation among the substitution pattern on rings A and B, the strength of the IHBs and the reduction potentials was found. NBO energies (Delta E-ij((2))) show that the main contributions to the stabilization of the IHBs arises from LP -> sigma* interactions. The strength of IHBs, given by Delta E-ij((2)), exhibit a notable quantitative correlation with the experimental reduction potential, which, at least to the best of our knowledge, has not been described before for any type of molecule. The results show the importance of the methoxy substitution pattern on the IHB and redox properties of these compounds. Our findings have potential implications in the design of antitumor chalcones.
机译：在这项工作中，我们介绍了一系列抗甲氧基化2'-羟基查耳酮的分子结构和电化学行为的研究，其抗肿瘤活性已在前面进行了描述。循环伏安法用于定量表征阴离子自由基的形成和稳定性。通过密度泛函理论（DFT）计算研究了中性化合物及其阴离子自由基的分子结构，特别是分子内氢键（IHB）。相对于中性物种，检查了阴离子的几何和边界轨道变化，并计算了绝热和垂直电子亲和力（AEA，VEA）以及垂直脱离能（VDE）。使用自然键轨道（NBO）分析来获得有关IHB电子特性的见解，并将结果与​​H-1-NMR化学位移相关。发现在环A和B上的取代方式，IHB的强度和还原电位之间存在直接关系。 NBO能量（ΔE-ij（（2）））表明，对IHBs稳定的主要贡献来自LP-> sigma *相互作用。由Delta E-ij（（2））给出的IHBs的强度与实验的还原电位表现出明显的定量相关性，至少就我们所知，对于任何类型的分子，以前都没有描述过。结果显示了甲氧基取代模式对这些化合物的IHB和氧化还原特性的重要性。我们的发现对抗肿瘤查耳酮的设计具有潜在的影响。

著录项

相似文献

  • 外文文献
  • 中文文献
  • 专利
获取原文

客服邮箱：kefu@zhangqiaokeyan.com

京公网安备：11010802029741号 ICP备案号：京ICP备15016152号-6 六维联合信息科技 (北京) 有限公司©版权所有

  • 客服微信

  • 服务号