Frost developed this mnemonic patterning as an extension of the HuckelHückel (4n+2$4n+2$) rule. A Frost diagram is usually applied to all-carbon, monocyclic, piπ systems. It allows one to find the number of molecular orbitals in the molecule's piπ system and their energetic positions. To construct a Frost diagram, proceed as follows:
- Draw a circle and inscribe a regular polygon with a vertex located at the bottom of the circle. IfThe polygon has the same shape as the ring you are interested in. For example, if you are interested in benzene, draw a hexagon,hexagon; for the tropylium ion, draw a heptagon.
- Energy-wise, the top and bottom of the circle are defined as $\ce{+2\beta}$$\alpha+2\beta$ and $\ce{-2\beta}$$\alpha-2\beta$ respectively (so the circle has radius $\ce{2\beta}$$2\beta$); the center of the circle is located at $\ce{0\beta}$$\alpha$; other points can be interpolated accordingly; the bottom of the circle is at lower energy than the top of the circle.
- Wherever a vertex of the polygon touches the circle, that is the energetic location of a molecular orbital.
- Include an $\ce{\alpha}$ in front of the $\ce{\beta}$ term in order to properly state the energy of the molecular orbital (MO)
Using benzene as an example, the lowest MO has energy $\ce{\alpha-2\beta}$$\alpha-2\beta$; the HOMO is degenerate (2 MO's) and located at $\ce{\alpha{-}\beta}$$\alpha-\beta$; the LUMO is also degenerate and located at $\ce{\alpha{+}\beta}$$\alpha+\beta$. Any orbital below the center of the circle is bonding, any orbital at the center is non-bonding and any orbital in the top-half of the circle is antibonding.