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Topological transformation of a trefoil knot into a [2]catenane
Dalton Transactions ( IF 3.5 ) Pub Date : 2017-10-23 00:00:00 , DOI: 10.1039/c7dt03582a Thirumurugan Prakasam 1, 2, 3, 4 , Rana A. Bilbeisi 5, 6, 7, 8, 9 , Roberto El-Khoury 1, 2, 3, 4 , Loïc J. Charbonnière 10, 11, 12, 13, 14 , Mourad Elhabiri 12, 13, 14, 15, 16 , Gennaro Esposito 1, 2, 3, 4, 17 , John-Carl Olsen 18, 19, 20, 21, 22 , Ali Trabolsi 1, 2, 3, 4
Dalton Transactions ( IF 3.5 ) Pub Date : 2017-10-23 00:00:00 , DOI: 10.1039/c7dt03582a Thirumurugan Prakasam 1, 2, 3, 4 , Rana A. Bilbeisi 5, 6, 7, 8, 9 , Roberto El-Khoury 1, 2, 3, 4 , Loïc J. Charbonnière 10, 11, 12, 13, 14 , Mourad Elhabiri 12, 13, 14, 15, 16 , Gennaro Esposito 1, 2, 3, 4, 17 , John-Carl Olsen 18, 19, 20, 21, 22 , Ali Trabolsi 1, 2, 3, 4
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Topological transformation of a zinc-templated trefoil knot, Zn-TK, into a zinc-templated [2]catenane, Zn-[2]C, was studied. The net reaction 2 Zn-TK → 3 Zn-[2]C was accomplished in 89% yield by heating a solution of Zn-TK in D2O. Kinetic investigation by 1H NMR spectroscopy and high resolution mass spectrometry revealed that the mechanism is complex, involving a large pool of intermediates that form after imine bond cleavage. Bromide ions, which can occupy the central cavity of Zn-TK, inhibited the reaction. Two similar transformations were also studied, one of a cadmium-containing trefoil knot, Cd-TK, into a cadmium-containing catenane, Cd-[2]C, and the other of Cd-TK into Zn-[2]C. The latter transformation could be achieved in one step at high temperature or in two steps via transmetallation to form Zn-TK at room temperature followed by topological conversion of Zn-TK to Zn-[2]C at high temperature.
中文翻译：
将三叶形结拓扑转换为[2]烷
研究了以锌为模板的三叶结Zn-TK拓扑转换为以锌为模板的[2]环戊烷Zn- [2] C的过程。通过加热Zn-TK在D 2 O中的溶液，完成了净反应2 Zn-TK → 3 Zn- [2] C的合成，收率89％。通过1 H NMR光谱和高分辨率质谱的动力学研究表明该机理它是复杂的，涉及亚胺键断裂后形成的大量中间体。可以占据Zn-TK中心腔的溴离子抑制了反应。还研究了两种类似的转化，一种含镉的三叶结Cd-TK成含镉索烃，CD-[2]Ç，其它的镉-TK成含有Zn [2]Ç。后者变换可以在一个步骤中在高温下可以实现或在两个步骤中通过金属转移形成的Zn-TK在室温下，随后的拓扑转换的Zn-TK到含有Zn [2]ç在高温下。
更新日期：2017-11-17
中文翻译：
将三叶形结拓扑转换为[2]烷
研究了以锌为模板的三叶结Zn-TK拓扑转换为以锌为模板的[2]环戊烷Zn- [2] C的过程。通过加热Zn-TK在D 2 O中的溶液，完成了净反应2 Zn-TK → 3 Zn- [2] C的合成，收率89％。通过1 H NMR光谱和高分辨率质谱的动力学研究表明该机理它是复杂的，涉及亚胺键断裂后形成的大量中间体。可以占据Zn-TK中心腔的溴离子抑制了反应。还研究了两种类似的转化，一种含镉的三叶结Cd-TK成含镉索烃，CD-[2]Ç，其它的镉-TK成含有Zn [2]Ç。后者变换可以在一个步骤中在高温下可以实现或在两个步骤中通过金属转移形成的Zn-TK在室温下，随后的拓扑转换的Zn-TK到含有Zn [2]ç在高温下。
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