What will be the effects of intramolecular hydrogen bonding on the stability of a molecule? Will it increase or decrease the overall stability of a molecule? Or will it not have any impact on the stability?

Why do I think intramolecular hydrogen bonding increases the stability?
I've learn that formation of a bond lowers the energy or increases the stability of a molecule. Thus, formation of intramolecular hydrogen bond makes the molecule more stable.

Why do I think intramolecular hydrogen bonding decreases the stability?
Let us consider the following molecule:

enter image description here

Intramolecular hydrogen bonding exists between oxygen atom of the carbonyl group and hydrogen atom of the hydroxyl group. Due to the hydrogen bond, these oxygen and hydrogen atoms are under attractive forces. I think this causes strain in the molecule, thereby increasing the energy or decreasing the stability of the molecule.

However, I don't know which of the above two arguments is correct. It would be helpful if you could explain the effects of intramolecular hydrogen bonding on the stability and the appropriate reason behind it.

  • $\begingroup$ Given that an unstabilizing effect won't take place you are left with a stabilization effect. This kind of doubts come from chemistry on paper. It might be related to phrasing. Besides this note, in the example sketched the effect is that of overall stabilization. The conformer giving room to internal H bond has in fact more bonds. Note that the formed cycle is not a strained one. But $\endgroup$ – Alchimista Feb 9 at 8:21
  • $\begingroup$ .... again in case of strained system the H bond won't take place. If it lowers stability perhaps only detailed mechanisms studies would be able to ascertain that (as for we can see the molecules with and without H bond as two different ones existing in equilibrium). $\endgroup$ – Alchimista Feb 9 at 8:22

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