How does singlet oxygen work in pericyclics?

Join the discussion
Ask a follow-up here, or get your own question answered by working scientists, mathematicians and engineers — people, not an autocomplete.
Real named experts · corrections over time · the nuance an AI answer skips
1 reply · 3K views
CrimpJiggler
Messages
141
Reaction score
1
0dd50c496df40e817213b79f87298753.png

and here's the diagram for the 1O2 dienophile:
1efc1d4587d91c99eaf8224ed3667f8d.png

Its the 1E+g the one I'm interested in. I see that its single electrons are in a couple of degenerate pi orbitals. I'm having trouble figuring out what the LUMO is here. Does it even matter that I have 2 LUMOs? I kinda suspect, that would make it much more reactive since unpaired electrons are pretty unstable. Is this oxygen singlet species technically a diradical?
 
Last edited:
Chemistry news on Phys.org
The MO diagram for singlet oxygen from wikipedia is not quite correct insofar as it is not a pi_x or pi_y orbital which is doubly occupied in singlet oxygen but rather a ##\pi^*_\pm=\frac{1}{\sqrt{2}}(\pi^*_x\pm i\pi^*_y)## orbital.
So let's say that the ##\pi^*_+## is doubly occupied, then the ##\pi^*_-## is the LUMO.