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截短四面体亚胺笼与铵离子的主客体化学

Host-Guest Chemistry of Truncated Tetrahedral Imine Cages with Ammonium Ions.

作者信息

Lauer Jochen C, Pang Ziwei, Janßen Paul, Rominger Frank, Kirschbaum Tobias, Elstner Marcus, Mastalerz Michael

机构信息

Organisch-Chemisches Institut Ruprecht-Karls-Universität Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Germany.

Institut für Physikalische Chemie Theoretische Chemische Biologie Universität Karlsruhe Geb. 30.44 Kaiserstr. 12 76131 Karlsruhe Germany.

出版信息

ChemistryOpen. 2020 Feb 3;9(2):183-190. doi: 10.1002/open.201900357. eCollection 2020 Feb.

DOI:10.1002/open.201900357
PMID:32025463
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6996569/
Abstract

Three shape-persistent [4+4] imine cages with truncated tetrahedral geometry with different window sizes were studied as hosts for the encapsulation of tetra--alkylammonium salts of various bulkiness. In various solvents the cages behave differently. For instance, in dichloromethane the cage with smallest window size takes up NEt but not NMe which is in contrast to the two cages with larger windows hosting both ions. To find out the reason for this, kinetic experiments were carried out to determine the velocity of uptake but also to deduce the activation barriers for these processes. To support the experimental results, calculations for the guest uptakes have been performed by molecular mechanics' simulations. Finally, the complexation of pharmaceutical interested compounds, such as acetylcholine, muscarine or denatonium have been determined by NMR experiments.

摘要

研究了三种具有截顶四面体几何形状且窗口尺寸不同的形状持久型[4+4]亚胺笼作为主体，用于封装各种体积大小的四烷基铵盐。在各种溶剂中，这些笼子表现不同。例如，在二氯甲烷中，窗口尺寸最小的笼子能容纳NEt，但不能容纳NMe，这与另外两个窗口较大的笼子能容纳两种离子形成对比。为找出其中原因，进行了动力学实验以确定摄取速度，并推导这些过程的活化能垒。为支持实验结果，通过分子力学模拟对客体摄取进行了计算。最后，通过核磁共振实验确定了乙酰胆碱、毒蕈碱或苯甲地那铵等药物相关化合物的络合情况。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/da1370ee9dae/OPEN-9-183-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/7118fcdbbdf9/OPEN-9-183-g011.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/4c820a7b39b3/OPEN-9-183-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/fbb9dd6a403b/OPEN-9-183-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/da1370ee9dae/OPEN-9-183-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/7118fcdbbdf9/OPEN-9-183-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/5310775255ce/OPEN-9-183-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/7db56ae0fe6c/OPEN-9-183-g002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/e428225a1aaa/OPEN-9-183-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/89bbdb91eb64/OPEN-9-183-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/e72e3d55a2f3/OPEN-9-183-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/f6b201f31736/OPEN-9-183-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/4c820a7b39b3/OPEN-9-183-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/fbb9dd6a403b/OPEN-9-183-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/630e/6996569/da1370ee9dae/OPEN-9-183-g010.jpg

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Chem Commun (Camb). 2019 Sep 19;55(76):11434-11437. doi: 10.1039/c9cc05968g.
3
Ammonium Complexes of Orthoester Cryptands Are Inherently Dynamic and Adaptive.原酸酯穴醚的铵配合物具有内在的动态性和适应性。
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Chemistry. 2022 Sep 12;28(51):e202201527. doi: 10.1002/chem.202201527. Epub 2022 Jul 21.
4
Examination of the Dynamic Covalent Chemistry of [2 + 3]-Imine Cages.[2 + 3] - 亚胺笼的动态共价化学研究
J Org Chem. 2020 Nov 6;85(21):13757-13771. doi: 10.1021/acs.joc.0c01887. Epub 2020 Oct 9.
5
A Giant [8+12] Boronic Ester Cage with 48 Terminal Alkene Units in the Periphery for Postsynthetic Alkene Metathesis.外围具有 48 个末端烯烃单元的[8+12]大硼酯笼用于后合成烯烃复分解反应。
Chemistry. 2021 Jan 4;27(1):233-237. doi: 10.1002/chem.202003675. Epub 2020 Nov 19.
6
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Angew Chem Int Ed Engl. 2020 Sep 14;59(38):16755-16763. doi: 10.1002/anie.202007571. Epub 2020 Jul 16.
J Am Chem Soc. 2019 Jun 5;141(22):8868-8876. doi: 10.1021/jacs.9b01350. Epub 2019 May 22.
4
Organic Imine Cages: Molecular Marriage and Applications.有机亚胺笼：分子结合与应用
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5
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