Glycerol- Three adjacent "OH" groups.

*I know that there is inter-molecular hydrogen bonding between the molecules of glycerol.

*What makes the adjacent alcohol groups behave differently towards each other as compared to when they interact through separate molecules?

*(additional question) - How many Carbon-Carbon single bonds worth do hydrogen bonds persist?

  • $\begingroup$ The hydrogen and oxygen are not close enough. If they made a 6-membered ring with the h-bond they might be, but here the best they can do is a 5-member ring and that is too far. $\endgroup$
    – matt_black
    Aug 18, 2020 at 13:45
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    $\begingroup$ @matt_black 5-membered rings are perfectly fine for h-bonds and OP is spawning nonsense here. $\endgroup$
    – Mithoron
    Aug 18, 2020 at 13:58
  • $\begingroup$ Do the adjacent "OH' have hydrogen bonds between each other? $\endgroup$
    – JKR
    Aug 18, 2020 at 14:09
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    $\begingroup$ @Mithoron Do you have an example? Given that a 'strong' hydrogen bond should have a ~180° angle around H, I wouldn't expect five membered rings to be anywhere large enough. $\endgroup$ Aug 18, 2020 at 15:44
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    $\begingroup$ @mithoron indeed, you're absolutely right. It is not strong, bit it would be wrong to disregard this interaction. // With that statement I meant that the hydrogen in the hydrogen bond should ideally be linearly coordinated, i.e. the bond angle $\angle\ce{O-H...O}\approx 180^\circ$. $\endgroup$ Aug 19, 2020 at 3:20


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