The frontier molecular orbital (FMO) theory has been widely adopted in recent years in the belief that it represents the best available qualitative/semiquantitative treatment of chemistry in terms of quantum theory. While the dubious nature of the approximation on which it is based has been recognized, its apparent success has been taken as sufficient justification. While it has also been recognized that it fails in certain cases, these have been regarded as rare consequences of special circumstances. The claim that FMO theory alone can account for the course of pericyclic reactions, if true, would certainly indicate its superiority to earlier theoretical treatments. However, no in-depth criticism of these claims has as yet been published. The purpose here is to provide such an analysis.

A critique of frontier orbital theory

Metathesis reactions of carbohydrates: Recent highlights in cross-metathesis

Steric effects vs secondary orbital interactions in nitrone cycloadditions : Steric effects in cycloreversions of isoxazolidines

Investigations on Peri-, Regio- and Stereoselectivities in Thermal Cycloadditions Involving C -(4-Oxo-4 H [1]benzopyran-3-yl)- N -phenylnitrones: Role of Steric Factors and Secondary Interactions in 1,3-Dipolar Cycloadditions

Bent bonds and the antiperiplanar hypothesis as a simple model to predict Diels–Alder reactivity: retrospective or perspective?

La cycloaddition du vinyl-1 cyclohexene au methoxycarbonyl-3 et -4 benzoquinones-1,2 obtenues in situ donne les monoadduits; la structure cristalline de ces 2 adduits est determinee par diffraction RX

Diels-Alder reaction between vinylcyclohexene and benzoquinones. A shortcoming of the FMO approach

On prepare un compose tricyclique de structure voisine de celle des precurseurs des podocarpanes, par cycloaddition du vinylcyclohexene avec l'acide benzoquinone-1,4 carboxylique. On etudie la structure cristalline du compose et on explique par une etude theorique la stereochimie de la reaction

9,10-syn-podocarpane diterpenoids. An approach to the tricyclic skeleton by Diels-Alder cycloaddition: related crystal structure determination and theoretical aspects

Ezio Abbondanti

Papers

Diels-Alder reaction between vinylcyclohexene and benzoquinones. A shortcoming of the FMO approach

9,10-syn-podocarpane diterpenoids. An approach to the tricyclic skeleton by Diels-Alder cycloaddition: related crystal structure determination and theoretical aspects