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EWGs enhance the Lewis acidity, making compounds more reactive as Lewis acids. For example, fluorine is a stronger electron-withdrawing substituent than methyl, resulting in an increased Lewis acidity of boron trifluoride relative to trimethylborane. Electron-withdrawing groups also tend to reduce Lewis basicity. [3]
Monochloroacetic acid (pK a =2.82), though, is stronger than formic acid, due to the electron-withdrawing effect of chlorine promoting ionization. In benzoic acid, the carbon atoms which are present in the ring are sp 2 hybridised. As a result, benzoic acid (pK a =4.20) is a stronger acid than cyclohexanecarboxylic acid (pK a =4.87).
It is generally considered an inductively withdrawing group (-I), because of the higher electronegativity of sp 2 carbon atoms, and a resonance donating group (+M), due to the ability of its π system to donate electron density when conjugation is possible. [5] The phenyl group is hydrophobic. Phenyl groups tend to resist oxidation and reduction.
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.
For meta-directing groups (electron withdrawing group or EWG), σ meta and σ para are more positive than σ’. (The superscript, c, in table denotes data from Hammett, 1940. [11] [page needed]) For ortho-para directing groups (electron donating group or EDG), σ’ more positive than σ meta and σ para.
An electron withdrawing group (EWG) will have the opposite effect on the nucleophilicity of the ring. The EWG removes electron density from a π system, making it less reactive in this type of reaction, [ 2 ] [ 3 ] and therefore called deactivating groups .
Vinylogous reactions are believed to occur when orbitals of the double bonds of the vinyl group and of an attached electron-withdrawing group (EWG; the π orbitals) are aligned and so can overlap and mix (i.e., are conjugated). Electron delocalization enables the EWG to receive electron density through participation of the conjugated system.
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 ...