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(S)-N-[(2-hydroxynaphthalen-1-yl)methylidene]valine – a valuable ligand for the preparation of chiral complexes
Inorganica Chimica Acta Pub Date : 2018-11-01 , DOI: 10.1016/j.ica.2018.08.011
Sandra Schwarzer , Uwe Böhme , Sabine Fels , Betty Günther , Erica Brendler

Abstract The reaction of (S)-N-[(2-hydroxynaphthalen-1-yl)methylidene]valine (H2L), 1, with organoelement halides from group 4 and 14 leads to different hypercoordinated complexes depending on the substitution of the starting material. The dianion of 1 therein acts as tridentate ligand in κ3O,N,O’ coordination mode. Complexes with silicon, germanium, tin, and titanium have been prepared in that way and are presented here as proof of concept. With one exception diorganoelement chlorides R2ECl2 yield pentacoordinate complexes LER2. Element tetrachlorides yield hexacoordinate complexes L2E. The prepared compounds were characterized via NMR, IR and UV/Vis spectroscopy, elemental and X-ray structure analysis. Furthermore solid state NMR measurements and chemical shift tensor analysis with the help of quantum chemical methods were used to investigate the electron density distribution around the central atoms of several products. This study demonstrates the ability of 1 to form chiral hypercoordinate complexes with different elements.

中文翻译:

(S)-N-[(2-羟基萘-1-基)亚甲基]缬氨酸–用于制备手性配合物的有价值的配体

摘要(S)-N-[(2-羟基萘-1-基)亚甲基]缬氨酸(H2L),1与第4组和第14组有机卤化物的反应导致不同的超配位络合物,具体取决于原料的取代。其中的二价阴离子在κ3O,N,O'配位模式下充当三齿配体。硅,锗,锡和钛的配合物已通过这种方式制备,并在此处作为概念证明提供。除了一个例外,双有机元素氯化物R2EC12产生五配位络合物LER2。元素四氯化物产生六配位络合物L2E。通过NMR,IR和UV / Vis光谱,元素和X射线结构分析来表征所制备的化合物。此外,固态NMR测量和借助量子化学方法的化学位移张量分析被用于研究几种产物中心原子周围的电子密度分布。这项研究表明1形成具有不同元素的手性超坐标配合物的能力。
更新日期:2018-11-01
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