Jump to main content
Jump to site search

Issue 15, 2011
Previous Article Next Article

Bent bonds, the antiperiplanar hypothesis and the theory of resonance. A simple model to understand reactivity in organic chemistry

Author affiliations

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.

Graphical abstract: Bent bonds, the antiperiplanar hypothesis and the theory of resonance. A simple model to understand reactivity in organic chemistry

Back to tab navigation

Publication details

The article was received on 13 Mar 2011, accepted on 12 May 2011 and first published on 12 May 2011


Article type: Perspective
DOI: 10.1039/C1OB05393K
Citation: Org. Biomol. Chem., 2011,9, 5321-5333
  •   Request permissions

    Bent bonds, the antiperiplanar hypothesis and the theory of resonance. A simple model to understand reactivity in organic chemistry

    G. Deslongchamps and P. Deslongchamps, Org. Biomol. Chem., 2011, 9, 5321
    DOI: 10.1039/C1OB05393K

Search articles by author

Spotlight

Advertisements