Chlorine and hydrogen bonding

Woopydalan

Does chlorine make a hydrogen bond? I was doing a practice problem in my book and the question was regarding the intermolecular forces, and the compound had chlorine and it said no, but my professor said it does. Which is true?

Drakkith

If it doesn't, could Hydrogen Chloride form?

chill_factor

That's a covalent bond between hydrogen and chlorine, not a hydrogen bond. Hydrogen bonds are a form of weak noncovalent bonding acting between molecules that contain O-H, N-H and F-H groups where the hydrogen is partially ionized.

Now whether chlorine participates in hydrogen bonding is something I don't know but I'll personally say "no".

JohnRC

There is not a Cl–H...X bond. (X = N, O, or F)
There might be some evidence for weak O–H...Cl hydrogen bonds in some cases.

AGNuke

The electronegativity of Nitrogen and Chlorine are almost same, and Nitrogen makes H-Bond, so yes, Chlorine also makes bond.

But the thing is that due to the size of chlorine, the electron density, which is required on chlorine for dipole-dipole attraction between partial positive H atom and partial negative Cl atom, is low, therefore, these "hydrogen" bonds are not strong enough to be comparable with Hydrogen bonds with N, O & F.