Figures index

From

Introduction of a Computational Chemistry Course-Based Undergraduate Research Experience (CURE) into an Advanced Organic Chemistry Lab: An Investigation of Propellane Formation

Phillip J. Alexander, Dillon Button-Jennings, Claudia N. Evans, Mason B. Hemstreet, Marissa E. Henager, Stephanie Jacob, Charles S. Jolly, Maayan R. Lantzman, Alexandra Saputo, Nolan R. Stager, Elizabeth L. Whitman, Bohdi J. Young, Gary W. Breton

World Journal of Chemical Education. 2021, 9(3), 88-93 doi:10.12691/wjce-9-3-4
  • Figure 1. The propellanes investigated in this study. The terms syn and anti are defined with respect to the one-carbon bridge
  • Scheme 1. Formation of [1.1.1] propellane via intramolecular attack of the anionic lone pair onto the bridgehead carbon bearing the bromo leaving group
  • Figure 2. (A) Structure of the PM3-optimized geometry of the [1.1.1] anionic bromide derivative. Note the intact C–Br bond. (B) Final structure observed upon B3LYP-optimization of the [2.2.2] anionic bromide. Note that the C–Br bond has been broken (the bromide ion is to the right of the structure) but no central propellane bond is formed. (C) Final structure observed upon B3LYP-optimization of the [3.2.2] anionic bromide. Note that the C–Br bond has been broken (the bromide ion has migrated behind the structure), and that in addition to the lack of a central propellane bond, one of the C2 bridges has broken to afford C=C bonds with the former bridgehead carbons