Bent Bonds, the Antiperiplanar Hypothesis and the Theory of Resonance. A Simple Model to Understand Reactivity in Organic Chemistry
The paper that started it all.
By taking into consideration bent bonds (τ-bonds, tau-bonds), the antiperiplanar hypothesis, the classic theory of resonance, and the preference for staggered bonds over eclipsed bonds in tetrahedral systems, a simple qualitative model is presented to rationalize the conformation and reactivity for a wide range of compounds containing double bonds and/or carbonyl groups. Alkenes, carbonyl and carboxyl derivatives, conjugated systems as well as other functional groups are revisited. This also leads to a simple model to understand aromaticity, and electrocyclic reactions. The bent bond model and the antiperiplanar hypothesis provide a qualitative model for better understanding the electron delocalization and the reactivity inherent to unsaturated organic systems by an alternative view of the classic resonance theory.
G. Deslongchamps, P. Deslongchamps, “Bent Bonds, the Antiperiplanar Hypothesis and the Theory of Resonance. A Simple Model to Understand Reactivity in Organic Chemistry“, Org. Biomol. Chem., 2011, 9, 5321-5333.
The paper was among the top ten most accessed articles for July 2011.