Chlorine and Hydrogen Bonding: Examining the Strength and Nature of Interactions

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Chlorine does not participate in hydrogen bonding in the same way that elements like nitrogen, oxygen, and fluorine do. Hydrogen bonds are weak noncovalent interactions that occur specifically between molecules containing O-H, N-H, or F-H groups, where hydrogen is partially ionized. While there may be some evidence for weak interactions such as O-H...Cl hydrogen bonds in certain cases, chlorine's size and lower electron density limit its ability to form strong hydrogen bonds. Consequently, hydrogen chloride (HCl) forms a covalent bond rather than a hydrogen bond, and chlorine's electronegativity is similar to nitrogen's, but this does not enable it to participate in hydrogen bonding effectively.
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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?
 
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If it doesn't, could Hydrogen Chloride form?
 
Drakkith said:
If it doesn't, could Hydrogen Chloride form?

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".
 
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.
 
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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.
 
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