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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.
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 .
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]
Groups that are electron-withdrawing by resonance decrease the electron density especially at positions 2, 4 and 6, leaving positions 3 and 5 as the ones with comparably higher reactivity, so these types of groups are meta directors (see below).
If the electronegative atom (missing an electron, thus having a positive charge) is then joined to a chain of atoms, typically carbon, the positive charge is relayed to the other atoms in the chain. This is the electron-withdrawing inductive effect, also known as the -I effect. In short, alkyl groups tend to donate electrons, leading to the +I ...
The +M effect, also known as the positive mesomeric effect, occurs when the substituent is an electron donating group. The group must have one of two things: a lone pair of electrons, or a negative charge. In the +M effect, the pi electrons are transferred from the group towards the conjugate system, increasing the density of the system.
The sulfonyl functional group (RS(O) 2 R') has become an important electron-withdrawing group for modern organic chemistry. α-Sulfonyl carbanions may be used as nucleophiles in alkylation reactions, Michael-type additions, and other processes. [3] After having served their synthetic purpose, sulfonyl groups are often removed.
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.