ArticleJournal of chemical education2017
A Teaching Experiment to Elucidate a Cation-π Effect in an Alkyne Cycloaddition Reaction and Illustrate Hypothesis Driven Design of Experiments.
Article in Journal of chemical education, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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1 citing paper in PubMed, 5 citations in OpenAlex.
- A Brief Introduction to Chemical Reaction Optimization.Chemical reviews · 2023Review
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5 authors at 1 institution in 1 country.
Funding
Abstract
An organic chemistry experiment is described that is based on recent research to elucidate a novel cation-π interaction between tetraalkammonium cations and propargyl hydrazines. This non-bonded interaction is a key component of the mechanism of ammonium-catalyzed intramolecular cycloaddition of nitrogen to the terminal carbon of a C-C triple bond of the propargyl substrate. In this teaching experiment, reactions and control experiments are employed to demonstrate the testing of two alternative mechanistic hypotheses. Specifically, cyclization reactions are performed with a soluble base (sodium phenoxide) with and without tetrabutylammonium bromide under homogeneous conditions. Students observe that the added ammonium salt accelerates the reaction. They are then encouraged to develop a testable hypothesis for the role of the ammonium salt in the cyclization mechanism: typical phase transfer or other. IR spectroscopy is then used to directly observe a dose dependent shift of the alkyne stretching mode due to a cation-π interaction. In this experiment, undergraduate "researchers" were able to practice the scientific method on a contemporary system and see how data are generated and interpreted to adjudicate between rival hypotheses in a way that emulates authentic and current research in a lab setting. This experimental design was tested on students enrolled in the introductory undergraduate Organic Chemistry Lab.
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