Electrophilic aromatic directing groups information
In electrophilic aromatic substitution reactions, existing substituent groups on the aromatic ring influence the overall reaction rate or have a directing effect on positional isomer of the products that are formed.
An electron donating group (EDG) or electron releasing group (ERG, Z in structural formulas) is an atom or functional group that donates some of its electron density into a conjugated π system via resonance (mesomerism) or inductive effects (or induction)—called +M or +I effects, respectively—thus making the π system more nucleophilic.[1][2] As a result of these electronic effects, an aromatic ring to which such a group is attached is more likely to participate in electrophilic substitution reaction. EDGs are therefore often known as activating groups, though steric effects can interfere with the reaction.
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.
EDGs and EWGs also determine the positions (relative to themselves) on the aromatic ring where substitution reactions are most likely to take place. Electron donating groups are generally ortho/para directors for electrophilic aromatic substitutions, while electron withdrawing groups (except the halogens) are generally meta directors. The selectivities observed with EDGs and EWGs were first described in 1892 and have been known as the Crum Brown–Gibson rule.[4]
^"Electron withdrawing group". Illustrated Glossary of Organic Chemistry. UCLA Department of Chemistry. Retrieved 16 November 2012.
^ abHunt, Ian. "Substituent Effects". University of Calgary Department of Chemistry. Retrieved 16 November 2012.
^"Electron donating group". Illustrated Glossary of Organic Chemistry. UCLA Department of Chemistry. Retrieved 16 November 2012.
^Brown, A. Crum; Gibson, John (1892). "XXX.—A rule for determining whether a given benzene mono-derivative shall give a meta-di-derivative or a mixture of ortho- and para-di-derivatives". J. Chem. Soc.61: 367–369. doi:10.1039/ct8926100367.
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