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I think the reason for this is the way that the electrons are distributed within the elements. The hydrogens have a more polar bond, so their electrons are distributed in a way that causes their bond to be stronger, whereas the ion-dipole bond has a greater distance between their electrons so their bond is weaker. It may be helpful to consider the size of the atoms too, smaller atoms (hydrogen) would have stronger bonds, and larger atoms would have a weaker bond.
The greater electronegativity of the hydrogen bond acceptor makes hydrogen bonds very strong. Hydrogen bonds are a form of dipole-dipole bonding, but it is stronger than other dipole-dipole interactions due to the electronegativity and the size is very small, allowing the H atoms to be closer to each other.
I believe the reason why Hydrogen Bonds are stronger than ion-dipole interactions is because Hydrogen bonds involve greater differences in electronegativity. This can then create a large electric dipole of positive and negative charges.
I know this topic has already been discussed thoroughly, but I always thought of hydrogen bonds as the "stronger of the weaker bonds" and the "weaker of the stronger bonds". The accuracy of this statement may be questionable, but it is a way I have always thought of hydrogen bonds in comparison to other bonds.
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