TABLE 2

Computationally obtained electronic effects of aromatic hydroxylation of quinoline The tetrahedral intermediate for aromatic hydroxylation of each position of quinoline was computationally modeled to obtain relative heats of formation of the tetrahedral intermediate.

Position
ΔΔHtetrahedral intermediatea
ΔΔG‡b
kcal/mol kcal/mol
2 5.19 1.47
3 6.26 3.04
4 2.17 0.73
5 0.77 0.95
6 6.17 2.08
7 6.67 2.20
8
0
0

  • ↵ a Relative heats of formation were used to calculate the relative activation energies

  • ↵ b Relative activation energies predict the electronically favored positions for aromatic hydroxylation of quinoline