Observing the Transient Assembly and Disassembly of Carboxylic Anhydrides in the Organic Chemistry Laboratory
Observing the Transient Assembly and Disassembly of Carboxylic Anhydrides in the Organic Chemistry Laboratory
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DOI：
10.1021/acs.jchemed.3c00731
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发表时间：
2023-12
影响因子：
3
通讯作者：
Sumalatha Peddi;Jacob R. Franklin;C. S. Hartley
中科院分区：
文献类型：
--
作者：
Sumalatha Peddi;Jacob R. Franklin;C. S. Hartley
模拟生物化学中ATP水解作用的化学反应是目前非平衡系统化学的研究热点。这些反应形成的瞬态键可以驱动分子机器或产生具有时间依赖特性的材料。虽然这些系统的行为可能很复杂，但潜在的化学成分通常很简单：因此，它们是有机化学本科入门学生潜在的有趣话题，将系统化学的最新进展与直接的反应相结合。在这里，我们开发了一个教学实验，探索在碳二亚胺水合作用下苯甲酸衍生物的瞬态组装。学生们以小组为单位，使用碳二亚胺“燃料”，研究两种苯甲酸中酸酐的形成和分解。学生们使用两种独立的方法，核磁共振和红外光谱来研究酸酐水解的经典反应动力学。然后，他们探索了碳二亚胺的数量如何影响苯甲酸酐沉淀的寿命，作为一个简单的不平衡自组装的例子。
Chemical reactions that mimic the function of ATP hydrolysis in biochemistry are of current interest in nonequilibrium systems chemistry. The formation of transient bonds from these reactions can drive molecular machines or generate materials with time-dependent properties. While the behavior of these systems can be complicated, the underlying chemistry is often simple: they are therefore potentially interesting topics for undergraduate introductory organic chemistry students, combining state-of-the-art advances in systems chemistry with straightforward reactions. Here, a teaching experiment has been developed that explores the transient assembly of benzoic acid derivatives driven by carbodiimide hydration. Working in teams, students examine the formation and decomposition of anhydrides from two benzoic acids using a carbodiimide “fuel”. The students examine classic reaction kinetics of anhydride hydrolysis using two independent methods, NMR and IR spectroscopies. They then explore how the amount of carbodiimide affects the lifetimes of precipitates of benzoic anhydride as a simple example of out-of-equilibrium self-assembly.