Why aren't the hydrogen bonds in carboxyllic acids like this?

Why don't carboxylic acids form H-bonds in this formation with the red dots (diagonal) instead of the black dots (horizontal)?

I was always taught that H-bonds formed between partially negative and partially positive atoms. I agree that the $$\ce{=O}$$ carboxyl oxygen is partially negative, so there should be a H-bond there from the partially positive H.

However, the $$\ce{O}$$ in $$\ce{OH}$$ is also partially negative. So why aren't the H-bonds denoted with red dots formed?

• And nobody told you that it goes straight to lone pair? – Mithoron Jul 29 at 13:55
• So, while bifurcated hydrogen bonds do exist, it's not the case here. – Mithoron Jul 29 at 15:53
• You need some degree of orbital overlap. Pretty challenging to overlap at that kind of angle. – Josh Mitchell Jul 29 at 16:08
• In reality in carboxylic acids, there are no double bond and single bond on oxygens. It is a hybrid (e.g., where is the $\ce{^{13}C}$-signal for carboxylic carbonyl in NMR?). – Mathew Mahindaratne Jul 29 at 17:52
• Often times you ignore the stuff that is not as important. It's a simple cartoon after all. – Buck Thorn Jul 29 at 20:34