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The mesomeric effect however, deals with restructuring and occurs when the electron pair of the substituents shift around. The inductive effect only acts on alpha carbons, while the mesomeric utilizes pi bonds between atoms. [4] While these two paths often lead to the similar molecules and resonance structures, the mechanism is different.
The strength of inductive effect is also dependent on the distance between the substituent group and the main group that react; the longer the distance, the weaker the effect. Inductive effects can be expressed quantitatively through the Hammett equation, which describes the relationship between reaction rates and equilibrium constants with ...
where is the ratio of the rate of the substituted reaction compared to the reference reaction, ρ* is the sensitivity factor for the reaction to polar effects, σ* is the polar substituent constant that describes the field and inductive effects of the substituent, δ is the sensitivity factor for the reaction to steric effects, and E s is ...
Field effects, F, are defined to include all effects (inductive and pure field). Likewise, effects due to resonance, R, are due to the average of electron-donating ability and electron-accepting ability. These two effects are assumed to be independent of each other and therefore can be written as a linear combination:
An electric effect influences the structure, reactivity, or properties of a molecule but is neither a traditional bond nor a steric effect. [1] In organic chemistry , the term stereoelectronic effect is also used to emphasize the relation between the electronic structure and the geometry ( stereochemistry ) of a molecule.
The inductive and resonance properties compete with each other but the resonance effect dominates for purposes of directing the sites of reactivity. For nitration, for example, fluorine directs strongly to the para position because the ortho position is inductively deactivated (86% para, 13% ortho, 0.6% meta).
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