Fused rings: decalins, adamantane, the steroid core

every carbon on a diamond-lattice point  ·  C–C 1.54 Å, all angles 109.47°, all dihedrals ±60°/180° ⌂ Home

Pick a structure

Ring-fusion geometry

Click a row to select those atoms in the model. At a fusion carbon the bond to the other ring is either equatorial (trans fusion) or axial (cis fusion) with respect to the first ring.

Exercise: count the gauche interactions

Compare trans- and cis-decalin: the difference in gauche count × 0.9 kcal/mol is the textbook explanation of why trans-decalin is more stable (≈ 2.7 kcal/mol).

Why the lattice matters

Every six-membered ring that can be drawn on the diamond lattice is automatically a perfect chair, and any number of chairs can be fused as long as each fusion bond is a lattice bond. A five-membered ring can never be placed on the lattice, which is why the steroid D ring is missing here (see the ring-strain module).

honestmolecules.com · © 2026 Thomas R. Hoye and Daniel Lee. All rights reserved. Free for classroom and personal study with attribution; no redistribution, modification, or commercial use without written permission.