3
$\begingroup$

This recent question about the gauche effect led me to read this rather older answer. The problem is that I notice I am still confused.

To take the case of 1,2 difluoroethane, I drew these orbitals: orbitals of C2H4F2 in the gauche (1,2) and anti (3,4) confromations Figure1: orbitals of $\ce{C2H4F2}$ in the gauche (1,2) and anti (3,4) confromations

Now I understand that 1 (gauche) leads to more stabilization than 3 (anti). But 2 (gauche) leads to less stabilization than 4 (anti). I don't know which effect is strongest: the destabilization in 2 or the stabilisation in 1. So I don't know why the gauche conformation (1,2) leads to more stabilization than the anti (3,4).

Did I draw something wong? Did I make a mistake in reasoning? Did I miss something else? Is this one too many error-acknowledgement questions?

$\endgroup$
2
  • $\begingroup$ The most important interaction in depicted in image 1. The energetic match of these oribtals is the best from all the listed. $\endgroup$
    – EJC
    Aug 4, 2016 at 15:41
  • $\begingroup$ Yes, but how do I know that it's enough to compensate for the loss of stabilization in 2 vs. 4? $\endgroup$
    – SCH
    Aug 4, 2016 at 15:55

1 Answer 1

1
$\begingroup$

In figures 2, it looks like you're saying the sigma of the C-F will be donating into the sigma* of the C-H, and that causes stabilization. However, a C-F sigma bond is a much poorer donor than a C-H due to the high electronegativity.

Since there is little to no donation actually occurring in 2 (or 4, for the matter) those interactions are much less relevant than depicted in 1/3 where there is significant donation for C-H sigma into C-F sigma*. Frankly I would never have even thought to draw 2/4 since there is so little electron density in the H lobe of the C-F sigma, but cool!

$\endgroup$
1
  • $\begingroup$ Wow I'd given up hope on this one. $\endgroup$
    – SCH
    Nov 17, 2021 at 16:32

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge that you have read and understand our privacy policy and code of conduct.

Not the answer you're looking for? Browse other questions tagged or ask your own question.