Understanding Thermodynamic Control in Covalent Self-Assembly: A Mixed Synthetic–Computational Experiment for the Undergraduate Organic-Chemistry Laboratory

• Adam G. L. Schafer ^[1] ; Ellen J. Yezierski ^[1] ; C. Scott Hartley ^[1]
  1. [1] Miami University

     Miami University

     Township of Oxford, Estados Unidos

     
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 96, Nº 6, 2019, págs. 1230-1235
• Idioma: inglés
• Texto completo no disponible (Saber más ...)
• Resumen

  • A laboratory experiment was developed that connects the interpretation of computer-generated models to the self-assembly of macrocycles. Students compare the reactions of terephthalaldehyde and isophthalaldehyde by reacting each with (R,R)-(−)-1,2-diaminocyclohexane. These isomeric systems serve as the foundation for a discussion about the impact of entropy and enthalpy on macrocycle formation. This experiment requires students to use multiple data sources to develop evidence-based explanations about the impact of the starting-material geometry on macrocyclization. Results from laboratory implementation indicate that a majority of students were able to successfully demonstrate competency of the learning goals.