Related Experiment Video
Updated: Mar 26, 2026

Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Interplay between aromaticity and strain in double group transfer reactions to 1,2-benzyne
Israel Fernández1, Fernando P Cossío2,3
1Departamento De Química Orgánica I, Facultad De Ciencas Químicas, Universidad Complutense De Madrid, Madrid, 28040, Spain.
Abstract:
Density Functional Theory calculations are used to explore the double hydrogen atom transfer from different alkanes to 1,2-benzyne. State-of-the-art calculations including the Activation Strain Model of reactivity, Energy Decomposition Analysis, and Valence Bond methods, reveal the origins of the relatively low activation barriers computed for these processes compared to the analogous reaction involving acetylene. In addition, the interplay between the in-plane aromaticity of the corresponding transition states and the variation of the π-aromaticity associated with the benzyne moiety as well as their influence on the barrier heights of the transformations are analyzed in detail.
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
NMR Spectroscopy of Benzene Derivatives
Conformations of Cycloalkanes
π Electron Effects on Chemical Shift: Aromatic and Antiaromatic Compounds
Directing and Steric Effects in Disubstituted Benzene Derivatives
¹H NMR: Long-Range Coupling
In alkenes, spin information is communicated via σ–π overlap, as seen in allylic (four-bond) and homoallylic (five-bond) couplings. These coupling interactions are stronger when the σ bond is parallel to the alkene...

