Exploring cation-π interactions in a sophomore Organic Chemistry Laboratory experiment

An Organic Chemistry Lab experiment is being developed and adapted from work recently published by Maity and Lepore [1] investigating the cyclization of substituted β-alkynyl hydrazines to yield azaproline derivatives. The mechanism of this reaction is putatively driven by cation-π interaction of alkynyl hydrazine with a tetrabutylammonium ion. This experiment will present students with a cutting-edge research concept to explore the role of tetrabutylammonium in the cyclization of substituted β-alkynyl hydrazines. Reaction kinetics will be probed by thin-layer chromatography and azaproline derivative product(s) will be characterized by IR spectroscopy. Ultimately, our goal is to implement a modern research-based, cost-effective, and safe bioorganic experiment into Florida Atlantic University’s undergraduate Organic Chemistry Laboratory curriculum.