Electron Withdrawing and Electron Donating Groups

Certain atoms or groups of atoms can add or withdrawal electron density to a system. Electron withdrawing groups EWG remove electron density from a system and tend to stabilize anions or electron rich structures. Conversely, EWG destabilize cations or electron poor structures. Electron donating groups EDG add electron density to a system and tend to stabilize cations or electron poor systems. Conversely, EDG destabilize anions or electron rich systems. There two ways electron density can distribute itself through a molecule. It can move through -bonds or through -bonds. The movement of electron density through -bonds is called inductive effects. The movement of electron density through -bonds is called resonance effects. Whether an atom or group of atoms is ED or EW by inductive effects or resonance effects depends on certain physical features such as electronegativity, lone pair electrons, and the presence of multiple bonds. Groups that are EWG inductively but EDG through resonance. These are electronegative atoms with lone pair electrons
X rarely an (EDG)R

Groups that are EDG only by inductive effects. Alkyl groups, the more branched, the more donating
CH3 CH2CH3 CH(CH3)2

OH NH2 the strongest (EDR)R

Groups that are EWG only by inductive effects. Atoms with no lone pair electrons but have a partial positive charge or a formal +1 charge.
F + C F F H H

Groups that are EWG by resonance. The atom that is attached to the molecule is involved in a multiple bond.

O CH O C R C N O C OR

+ N H

Groups that are EWG inductively and EWG by resonance.

+ O N = -NO2 O since the nitro group is both (EWG)i and (EWG)r it is the strongest EWG

Groups that can be either EWG or EDG by resonance.

C CH2 H