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Main arene substitution patterns. In ortho-substitution, two substituents occupy positions next to each other, which may be numbered 1 and 2. In the diagram, these positions are marked R and ortho. In meta-substitution the substituents occupy positions 1 and 3 (corresponding to R and meta in the diagram). In para-substitution, the substituents ...
Electrophilic aromatic substitution (SEAr) is an organic reaction in which an atom that is attached to an aromatic system (usually hydrogen) is replaced by an electrophile. Some of the most important electrophilic aromatic substitutions are aromatic nitration, aromatic halogenation, aromatic sulfonation, alkylation Friedel–Crafts reaction and ...
Electrophilic aromatic directing groups. 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 ...
Ortho effect is an organic chemistry phenomenon where the presence of a chemical group at the at ortho position or the 1 and 2 position of a phenyl ring, relative to the carboxylic compound changes the chemical properties of the compound. This is caused by steric effects and bonding interactions along with polar effects caused by the various ...
Hammett equation. In organic chemistry, the Hammett equation describes a linear free-energy relationship relating reaction rates and equilibrium constants for many reactions involving benzoic acid derivatives with meta- and para- substituents to each other with just two parameters: a substituent constant and a reaction constant. [1][2] This ...
Directed ortho metalation. Directed ortho metalation (DoM) is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho- position of a direct metalation group or DMG through the intermediary of an aryllithium compound. [1] The DMG interacts with lithium through a hetero atom.
Directed ortho metalation. Directed ortho metalation is an important tool in the synthesis of regiospecific substituted aromatic compounds. This approach to lithiation and subsequent quenching of the intermediate lithium species with electrophile is often better than the electrophilic aromatic substitution due to its high regioselectivity.
Monosubstituted phenyl groups (that is, disubstituted benzenes) are associated with electrophilic aromatic substitution reactions and the products follow the arene substitution pattern. So, a given substituted phenyl compound has three isomers, ortho (1,2-disubstitution), meta (1,3-disubstitution) and para (1,4-disubstitution). A disubstituted ...