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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.
Also, in aromatic carboxylic acids, electron-withdrawing groups substituted at the ortho and para positions can enhance the acid strength. Since the carboxyl group is itself an electron-withdrawing group, dicarboxylic acids are, in general, stronger acids than their monocarboxyl analogues. The Inductive effect will also help in polarization of ...
Diagram showing the ortho, meta and para positions relative to a substituent X on a benzene ring. Electron donating groups are typically divided into three levels of activating ability (The "extreme" category can be seen as "strong".) Electron withdrawing groups are assigned to similar groupings.
With respect to acidity, a common trend to note is that, inductively, an electron-withdrawing substituent in the vicinity of an acidic proton will lower the pKa (i.e. increase the acidity) and, correspondingly, an electron-donating substituent will raise the pKa. [7] The reorganization of charge due to field effects will have the same result.
The effect is used in a qualitative way and describes the electron withdrawing or releasing properties of substituents based on relevant resonance structures and is symbolized by the letter M. [2] The mesomeric effect is negative ( –M ) when the substituent is an electron-withdrawing group , and the effect is positive ( +M ) when the ...
The more positive is the value of sEDA the more sigma-electron donating is a substituent. The more negative sEDA, the more sigma-electron withdrawing is the substituent (see the table below). The sEDA parameter for a given substituent is calculated by means of quantum chemistry methods. The model molecule is the monosubstituted benzene.
The captodative effect is the stabilization of radicals by a synergistic effect of an electron-withdrawing substituent and an electron-donating substituent. [2] [3] The name originates as the electron-withdrawing group (EWG) is sometimes called the "captor" group, whilst the electron-donating group (EDG) is the "dative" substituent. [3]
When this center is an electron rich carbanion or an alkoxide anion, the presence of the electron-withdrawing substituent has a stabilizing effect. Similarly, an electron-releasing group (ERG) or electron-donating group (EDG) releases electrons into a reaction center and as such stabilizes electron deficient carbocations.