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Exercises · 4.39

Q.Define hydrogen bond. Is it weaker or stronger than the van der Waals forces?

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A hydrogen bond is an electrostatic attraction between a hydrogen atom covalently bonded to a highly electronegative atom (N, O, or F) and another electronegative atom with a lone pair. It is significantly stronger than van der Waals forces, typically 5–10 times the strength of dipole-dipole interactions.

What is a hydrogen bond?

A hydrogen bond isn't a true chemical bond in the covalent or ionic sense. Instead, it's a special type of intermolecular force that arises under very specific conditions.

The key players are:

  • A hydrogen atom covalently bonded to a highly electronegative atom (nitrogen, oxygen, or fluorine)
  • Another electronegative atom nearby that has at least one lone pair of electrons

When hydrogen bonds to N, O, or F, the bond is so polar that hydrogen becomes partially positive (δ+\delta^+) to an unusual degree—almost like a bare proton with a tiny electron cloud. This exposed positive charge is then attracted to the lone pair on another electronegative atom, creating a bridge between molecules.

We represent it as: X−H ⋯Y\ce{X-H \cdots Y}, where X\ce{X} and Y\ce{Y} are N, O, or F, and the dotted line shows the hydrogen bond.

Classic examples:

  • Water (HX2O\ce{H2O}): Each molecule can form up to four hydrogen bonds (two through its hydrogens, two through its lone pairs)
  • Ammonia (NHX3\ce{NH3}): Forms hydrogen bonds through its N–H bonds
  • DNA base pairs: Adenine-thymine (2 H-bonds) and guanine-cytosine (3 H-bonds)
  • Proteins: Hydrogen bonds stabilize secondary structures like α-helices and β-sheets
Important

The three requirements for hydrogen bonding:

  1. Hydrogen must be covalently bonded to N, O, or F
  2. A nearby electronegative atom must have a lone pair
  3. The geometry must allow the H and lone pair to approach closely (typically 1.5–2.5 Å)

Strength comparison with van der Waals forces

Van der Waals forces is an umbrella term covering three types of weak intermolecular attractions:

TypeOriginTypical strength
London dispersionTemporary dipoles from electron movement0.5–2 kJ/mol
Dipole-dipolePermanent dipoles in polar molecules2–5 kJ/mol
Dipole-induced dipolePolar molecule inducing dipole in nonpolar1–3 kJ/mol

Hydrogen bonds, by contrast, have energies of 10–40 kJ/mol—roughly an order of magnitude stronger than typical van der Waals forces, though still much weaker than covalent bonds (150–400 kJ/mol).

Why the difference? Hydrogen bonding involves: …

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