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水中亚胺离子的分子识别与稳定化

Molecular recognition and stabilization of iminium ions in water.

作者信息

Dong Vy M, Fiedler Dorothea, Carl Barbara, Bergman Robert G, Raymond Kenneth N

机构信息

Department of Chemistry, University of California, Berkeley, California 94720-1460, USA.

出版信息

J Am Chem Soc. 2006 Nov 15;128(45):14464-5. doi: 10.1021/ja0657915.

DOI:10.1021/ja0657915
PMID:17090022
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2562236/
Abstract

Iminium ions are known to exist only transiently in aqueous solution due to their high reactivity toward hydrolysis. In this communication, we report on the generation and stabilization of iminium ions in aqueous solution via molecular encapsulation using a K12Ga4L6 host. Our studies revealed that tetrahedral host 1 can encapsulate a variety of iminium cations in a molecular recognition process that is selective based on the charge, hydrophobicity, size, and shape of the guest.

摘要

由于亚胺离子对水解具有高反应活性,已知其仅在水溶液中短暂存在。在本通讯中,我们报道了通过使用K12Ga4L6主体进行分子包封,在水溶液中生成并稳定亚胺离子。我们的研究表明,四面体主体1可以在基于客体的电荷、疏水性、大小和形状具有选择性的分子识别过程中包封多种亚胺阳离子。

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本文引用的文献

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Self-fulfilling cavitands: packing alkyl chains into small spaces.自我实现的空穴化合物:将烷基链填充到小空间中。
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Design, formation and properties of tetrahedral M(4)L(4) and M(4)L(6) supramolecular clusters.四面体M(4)L(4)和M(4)L(6)超分子簇的设计、形成与性质
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Stabilization of a Reactive Cationic Species by Supramolecular Encapsulation Coordination Number Incommensurate Cluster Formation, Part 15. This research was supported by NSF grant CHE-9709621. We gratefully acknowledge Prof. Julie A. Leary and Dr. Ulla Andersen for their assistance with mass spectrometry. We also thank the Miller Foundation for a postdoctoral fellowship to M.Z. and the NIH for a postdoctoral fellowship to J.L.B. Part 14: J. Xide, K. N. Raymond, Angew. Chem. 2000, 112, 2857-2859; Angew. Chem. Int. Ed. 2000, 39, 2745-2747.通过超分子包封稳定反应性阳离子物种:配位数不匹配簇的形成,第15部分。本研究得到美国国家科学基金会(NSF)CHE - 9709621号资助。我们非常感谢朱莉·A·利里教授和乌拉·安德森博士在质谱分析方面提供的帮助。我们还要感谢米勒基金会为M.Z.提供博士后奖学金,以及美国国立卫生研究院(NIH)为J.L.B.提供博士后奖学金。第14部分:J. 西德,K. N. 雷蒙德,《德国应用化学》,2000年,112卷,2857 - 2859页;《德国应用化学》国际版,2000年,39卷,2745 - 2747页。
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Virtual combinatorial libraries: dynamic generation of molecular and supramolecular diversity by self-assembly.虚拟组合库:通过自组装动态生成分子和超分子多样性。
Proc Natl Acad Sci U S A. 1997 Mar 18;94(6):2106-10. doi: 10.1073/pnas.94.6.2106.