Saura-Sanmartin Adrian, Lopez-Sanchez Jorge, Lopez-Leonardo Carmen, Pastor Aurelia, Berna Jose
Departamento de Química Orgánica, Facultad de Química, Regional Campus of International Excellence "Campus Mare Nostrum", Universidad de Murcia, E-30100 Murcia, Spain.
J Chem Educ. 2023 Aug 1;100(9):3355-3363. doi: 10.1021/acs.jchemed.3c00163. eCollection 2023 Sep 12.
The synthesis of a [2]rotaxane through three- or five-component coupling reactions has been adapted to an organic chemistry experiment for upper-division students. The experimental procedure addresses the search for the most favorable reaction conditions for the synthesis of the interlocked compound, which is obtained in a yield of up to 71%. Moreover, the interlocked nature of the rotaxane is proven by NMR spectroscopy. The content of the sessions has been designed on the basis of a proactive methodology whereby upper-division undergraduate students have a dynamic role. The laboratory experience not only introduces students to the chemistry of the mechanical bond but also reinforces their previous knowledge of basic organic laboratory procedures and their skills with structural elucidation techniques such as NMR and FT-IR spectroscopies. The experiment has been designed in such a customizable way that both experimental procedures and laboratory material can be adapted to a wide range of undergraduate course curricula.
通过三组分或五组分偶联反应合成[2]轮烷已被改编为面向高年级学生的有机化学实验。实验步骤涉及寻找合成互锁化合物的最有利反应条件，该化合物的产率高达71%。此外，通过核磁共振光谱法证明了轮烷的互锁性质。课程内容基于一种积极主动的方法进行设计，使高年级本科生发挥动态作用。实验室体验不仅向学生介绍了机械键的化学知识，还强化了他们之前对基础有机实验室操作的了解以及使用核磁共振和傅里叶变换红外光谱等结构解析技术的技能。该实验的设计具有高度可定制性，实验步骤和实验室材料都可以适应广泛的本科课程设置。
