Substitution électrophile aromatique dans l'anhydride sulfureux liquide. Etude cinétique de la réaction de bromation d'anisoles monosubstitués. Transmission des effets électroniques et caractéristiques de l'état de transition
✍ Scribed by Paul Castellonèse; Pierre Villa
- Publisher
- John Wiley and Sons
- Year
- 1983
- Tongue
- German
- Weight
- 457 KB
- Volume
- 66
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Reactivity‐structure correlations for anisole and eleven of its substituted derivatives established from bromination rate constants in liquid SO~2~, unlike observations in water, show the reaction to be highly sensitive to substituent effects, (ρ = −7.1; ρ = −10.51). This result is ascribed to the solvation of the methoxy group which decreases the conjugation of para‐substituted (ρ = −9.70) compared to that of ortho‐substituted derivatives (ρ = −8.86). The highly solvated transition state lies far from reactants on the reaction coordinate and the positive charge developed in this state is nearly unity.