Publication:
Exploring the Chemistry of the Mechanical Bond: Synthesis of a [2]Rotaxane through Multicomponent Reactions

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Exploring the Chemistry of the Mechanical Bond Synthesis of a [2]Rotaxane through Multicomponent Reactions.pdf(3.22 MB)
Date
2023-08-01
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Authors
Saura Sanmartín, Adrián ; Lopez-Sanchez, Jorge ; Lopez-Leonardo, Carmen ; Pastor Vivero, Aurelia ; Berná, José
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Saura Sanmartín, Adrián ; Berná, José
Publisher
American Chemical Society and Divisionof Chemical Education,Inc
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Química Orgánica
DOI
https://doi.org/10.1021/acs.jchemed.3c00163
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info:eu-repo/semantics/article
Description
© 2023 The Authors. Published by American Chemical Society and Division of Chemical Education, Inc. This manuscript version is made available under the CC-BY 4.0 license https://creativecommons.org/licenses/by/4.0/ This document is the Published Manuscript version of a Published Work that appeared in final form in Journal of Chemical Education. To access the final edited and published work see https://doi.org/10.1021/acs.jchemed.3c00163
Abstract
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.
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Nuclear magnetic resonance spectroscopy , Rotaxanes , Students , Supramolecular chemistry , Undergraduates
Citation
Journal of Chemical Education, 100, 9, 2023, 3355–3363
URI
http://hdl.handle.net/10201/135765
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