The Melting Point Alternation inα,ω-Alkanediols andα,ω-Alkanediamines: Interplay between Hydrogen Bonding and Hydrophobic Interactions

Efficient hydrophobic packing, driven by molecular offset within the hydrogen-bonded layers of α,ω-alkanediols and diamines, is allowed by the geometry of the even-numbered members (left in the picture). In contrast, the geometry of the odd-numbered members (right in the picture) forbids such packing and leads to the observed density and melting point alternation.