Abstract
Qualitative potential energy surfaces for electrophilic, photoelectrophilic, nucleophilic, and photonucleophilic aromatic substitutions are constructed and selection rules are derived. It is predicted that the regiochemistry of electrophilic and photonucleophilic aromatic substitutions is controlled by the electron density of the highest occupied MO of the aromatic substrate. On the other hand, the regiochemistry of nucleophilic and photoelectrophilic aromatic substitutions is controlled by the electron density of the lowest unoccupied MO of the aromatic substrate. The dependence of reaction rate and selectivity on polarity is discussed.
| Original language | English |
|---|---|
| Pages (from-to) | 29-33 |
| Number of pages | 5 |
| Journal | Journal of the American Chemical Society |
| Volume | 100 |
| Issue number | 1 |
| DOIs | |
| State | Published - 1978 |
| Externally published | Yes |