Addition/Correction Cite This: J. Chem. Educ. XXXX, XXX, XXX-XXX
pubs.acs.org/jchemeduc
Correction to “Pericyclic or Pseudopericyclic? The Case of an Allylic Transposition in the Synthesis of a Saccharin Derivative” Stephanie R. Hare and Dean J. Tantillo* J. Chem. Educ. 2017, 94 (8), 988−993. DOI: 10.1021/acs.jchemed.6b00825 In Figure 3 (top row) and Figure 4, structures for the reactant and product were inaccurately positioned. The corrected Figures 3 and 4 are shown.
Figure 3. Top row: Optimized structures of the reactant, transition state, and product of this reaction and their electronic energies (in kcal/mol) relative to the reactant structure, calculated at the B3LYP/6-31G(d) level of theory. Bottom row: The left and middle images show two orientations of the transition state structure to emphasize that the geometry of the migrating group remains “pointing” at the lone pairs of oxygen and nitrogen. The right picture depicts a natural bond orbital calculation result showing overlap between the formally empty p orbital on the migrating methylene and one of the lone pairs on oxygen. All of the orbitals shown have an isovalue of 0.06. See the Supporting Information for details on this type of calculation.
© 2017 American Chemical Society and Division of Chemical Education, Inc.
A
DOI: 10.1021/acs.jchemed.7b00609 J. Chem. Educ. XXXX, XXX, XXX−XXX
Journal of Chemical Education
Addition/Correction
Figure 4. Energy changes along the intrinsic reaction coordinate (IRC) associated with the pseudopericyclic transition state structure (B3LYP/3-21G). Pictures of structures at the points marked in red on the chart are shown with their electronic energies (in kcal/mol) relative to the reactant structure.
B
DOI: 10.1021/acs.jchemed.7b00609 J. Chem. Educ. XXXX, XXX, XXX−XXX
