Single-Crystal X-ray Analysis of the Diketo form of Asymmetric Curcuminoids and Coupled with NMR Insights into Its β-Keto-enol Tautomerization at Ambient Temperature
學年 113
學期 1
出版（發表）日期 2024-08-26
作品名稱 Single-Crystal X-ray Analysis of the Diketo form of Asymmetric Curcuminoids and Coupled with NMR Insights into Its β-Keto-enol Tautomerization at Ambient Temperature
作品名稱（其他語言）
著者 Cheng, Yang-je; Lin, Jyun-yi; Shih, Tzenge-lien; Hsieh, Chung-hung
單位
出版者
著錄名稱、卷期、頁數 Journal of the Chinese Chemical Society 71(11),　p.1396-1401
摘要 In this study, we present a detailed analysis of the structural forms of asymmetric curcuminoids through single-crystal X-ray diffraction and nuclear magnetic resonance (NMR) spectroscopy. Curcuminoids substituted with electron-withdrawing groups (Cl and Br) predominantly adopt the β-keto-enol form, whereas those with an OMe group exhibit both diketo and β-keto-enol forms. Variable-temperature X-ray diffraction studies confirm that the structural state of curcuminoids is influenced by temperature. Our findings also reveal that the β-keto-enol form is favored in acidic and neutral conditions, while the diketo form is more prevalent in basic environments. The theoretical Density Functional Theory (DFT) calculations further elucidate the energy differences between the diketo and β-keto-enol forms, emphasizing the significance of electronic effects and temperature on tautomeric distributions. These insights enhance our understanding of the structural dynamics of curcuminoids, with implications for their biological activity and pharmacological applications.
關鍵字 β-keto-enol tautomerization;curcuminoids;DFT calculations;NMR spectroscopy;structural analysis;X-ray crystallography
語言 en_US
ISSN 2192-6549
期刊性質 國內
收錄於 SCI
產學合作
通訊作者
審稿制度 否
國別 TWN
公開徵稿
出版型式 ,電子版
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機構典藏連結 ( http://tkuir.lib.tku.edu.tw:8080/dspace/handle/987654321/126480 )