Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5222929 | Tetrahedron | 2009 | 7 Pages |
Abstract
Ring strain energies (RSEs) of heterocyclic compounds are predicted compared to their analogous homocyclic compounds using the G3 method. Suitable reference compounds are devised for row 2 and row 3 heterobicyclic alkenes. Any difference in energy between the ring and the reference is due to RSE. Row 3 heterobicyclic alkene RSEs are less than those of row 2. As the electronegativity of the heteroatom increases, the RSE increases. Substitutents at the bridgehead carbons cause a decrease in RSE. [3.2.1] Heterobicyclic alkenes are significantly less strained than their [2.2.1] counterparts. Relative and absolute RSEs are reported for heterobicyclic alkenes and their derivatives.
Graphical abstractDownload full-size image
Keywords
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Jennifer Howell, John D. Goddard, William Tam,