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In Organic chemistry, the inductive effect in a molecule is a local change in the electron density due to electron-withdrawing or electron-donating groups elsewhere in the molecule, resulting in a permanent dipole in a bond. [1] It is present in a σ (sigma) bond, unlike the electromeric effect which is present in a π (pi) bond.
The inductive effect is the transmission of charge through covalent bonds and Bent's rule provides a mechanism for such results via differences in hybridisation. In the table below, [ 26 ] as the groups bonded to the central carbon become more electronegative, the central carbon becomes more electron-withdrawing as measured by the polar ...
The polarization of a molecule through its bonds is a separate phenomenon known as induction. [3] Field effects are relatively weak, and diminish rapidly with distance, but have still been found to alter molecular properties such as acidity. [1] Field effect on a carbonyl arising from the dipole in a C-F bond.
Electron-withdrawing groups exert an "inductive" or "electron-pulling" effect on covalent bonds. The strength of the electron-withdrawing group is inversely proportional to the pKa of the carboxylic acid. [2] The inductive effect is cumulative: trichloroacetic acid is 1000x stronger than chloroacetic acid.
In organic carboxylic acids, an electronegative substituent can pull electron density out of an acidic bond through the inductive effect, resulting in a smaller value. The effect decreases, the further the electronegative element is from the carboxylate group, as illustrated by the following series of halogenated butanoic acids .
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:
This effect is depicted in scheme 3, where, in a para substituted arene 1a, one resonance structure 1b is a quinoid with positive charge on the X substituent, releasing electrons and thus destabilizing the Y substituent. This destabilizing effect is not possible when X has a meta orientation. Scheme 3. Hammett Inductive Mesomeric Effects
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 ...