Investigation of two- and three-bond carbon-hydrogen coupling constants in cinnamic acid based compounds

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• 作者：Gregory K. Pierens ; Taracad K. Venkatachalam and David C. Reutens
• 刊名：Magnetic Resonance in Chemistry
• 出版年：2016
• 出版时间：December 2016
• 年：2016
• 卷：54
• 期：12
• 页码：941-946
• 全文大小：1352K
• ISSN：1097-458Xa

文摘

Two- and three-bond coupling constants (²J_HC and ³J_HC) were determined for a series of 12 substituted cinnamic acids using a selective 2D inphase/antiphase (IPAP)-single quantum multiple bond correlation (HSQMBC) and 1D proton coupled ¹³C NMR experiments. The coupling constants from two methods were compared and found to give very similar values. The results showed coupling constant values ranging from 1.7 to 9.7 Hz and 1.0 to 9.6 Hz for the IPAP-HSQMBC and the direct ¹³C NMR experiments, respectively. The experimental values of the coupling constants were compared with discrete density functional theory (DFT) calculated values and were found to be in good agreement for the ³J_HC. However, the DFT method under estimated the ²J_HC coupling constants. Knowing the limitations of the measurement and calculation of these multibond coupling constants will add confidence to the assignment of conformation or stereochemical aspects of complex molecules like natural products. Copyright