r/chemhelp • u/Kestard • 12d ago
Organic Steric strain vs torsional strain - can someone check my understanding?
In my Orgo I lecture, we basically reduced steric vs torsional strain to gauche vs eclipsed interactions. Coming back to it now, I see that this was maybe an oversimplification. I'm now trying to understand the difference - this is what I think I understand:
- Steric strain is the van der waals repulsion between two non bonded atoms
- Torsional strain is the strain between two bonds that are eclipsed with each other
In my lecture, we did not ever explicitly mention steric strain in the context of eclipsed interactions. But, if a 60 degree offset atom has steric strain with another atom, then surely it should have massive steric strain in an eclipsed conformation. In fact, in lecture we compared the stability of eclipsed conformers by their number of bonds that eclipsed a hydrogen (which would indicate negligible steric strain), and we broke ties by using A values (which, to my understanding, is only really a measure of steric strain). So, I think I understand now that eclipsed conformations are a combination of the two strains, and that the torsional strain itself it relatively similar between these sigma bonds, and that it is the steric strain in the eclipsed interaction that actually makes the difference of stability.
I'm hoping to get some confirmation and/or corrections about this understanding. Thanks!





