Which Hydrogen Bond is Stronger: Intermolecular or Intramolecular?

Intramolecular hydrogen bonds are generally stronger than intermolecular hydrogen bonds.

• Intramolecular: These occur within a single molecule, pulling its structure tighter and often impacting its reactivity and shape. Because the hydrogen and electronegative atoms are held so close together within the molecule, the bond is strong.
• Intermolecular: These occur between different molecules. While still important, such as in holding water molecules together, they are weaker because the molecules are not as tightly bound.

Thus, compounds with strong intramolecular hydrogen bonding are often less able to form hydrogen bonds with water, affecting solubility and boiling point.