氘同位素效应对 10-羟基苯并[h]喹啉的 ¹³C-NMR 化学位移的影响。
Deuterium isotope effects on ¹³C-NMR chemical shifts of 10-hydroxybenzo[h]quinolines.
机构信息
Department of Science, Systems and Models, Roskilde University, P.O. Box 260, DK-4000 Roskilde, Denmark.
出版信息
Molecules. 2013 Apr 17;18(4):4544-60. doi: 10.3390/molecules18044544.
Deuterium isotope effects on ¹³C-NMR chemical shifts are investigated in a series of 10-hydroxybenzo[h]quinolines (HBQ's) The OH proton is deuteriated. The isotope effects on ¹³C chemical shifts in these hydrogen bonded systems are rather unusual. The formal four-bond effects are found to be negative, indicating transmission via the hydrogen bond. In addition unusual long-range effects are seen. Structures, NMR chemical shifts and changes in nuclear shieldings upon deuteriation are calculated using DFT methods. Two-bond deuterium isotope effects on 13C chemical shifts are correlated with calculated OH stretching frequencies. Isotope effects on chemical shifts are calculated for systems with OH exchanged by OD. Hydrogen bond potentials are discussed. New and more soluble nitro derivatives are synthesized.
氘同位素效应对一系列 10-羟基苯并[h]喹啉（HBQ）的 ¹³C-NMR 化学位移的影响进行了研究。OH 质子被氘化。在这些氢键体系中，对 ¹³C 化学位移的同位素效应相当不寻常。发现正式的四键效应为负，表明通过氢键进行传递。此外，还观察到不寻常的远程效应。使用 DFT 方法计算结构、NMR 化学位移和氘化时核屏蔽的变化。对 13C 化学位移的两键氘同位素效应与计算出的 OH 伸缩频率相关联。对 OH 被 OD 取代的系统计算了同位素对化学位移的影响。讨论了氢键势。合成了新的、更易溶的硝基衍生物。
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