title: Bent bonds, the antiperiplanar hypothesis and the theory of resonance. A simple model to understand reactivity in organic chemistry.
abstract: 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.
authors.affiliation: Department of Chemistry, University of New Brunswick, P. O. Box 4400, Fredericton, NB, Canada E3B 5A3. ghislain@unb.ca
authors.forename: Ghislain
authors.initials: G
authors.lastname: Deslongchamps
authors.forename: Pierre
authors.initials: P
authors.lastname: Deslongchamps