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In meta-substitution, the substituents occupy positions 1 and 3 (corresponding to R and meta in the diagram). In para-substitution, the substituents occupy the opposite ends (positions 1 and 4, corresponding to R and para in the diagram). The toluidines serve as an example for these three types of substitution.
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.
Electrophilic aromatic substitution (S E Ar) 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 ...
The ortho to para selectivity is low: [7] No reaction takes place when the solvent is replaced by tetrachloromethane. In contrast, when the reactant is 2-phenylethylamine, it is possible to employ relatively apolar solvents with exclusive ortho-regioselectivity due to the intermediate formation of a chloramine, enabling the Intramolecular reaction.
For nitration, for example, fluorine directs strongly to the para position because the ortho position is inductively deactivated (86% para, 13% ortho, 0.6% meta). On the other hand, iodine directs to ortho and para positions comparably (54% para and 45% ortho, 1.3% meta). [12]
Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a functional group in a compound, which is typically, but not always, aromatic. Aromatic substitution reactions are characteristic of aromatic compounds and are common ways of introducing functional groups into benzene rings.
Steric inhibition of protonation caused by substitution of anilines to become weaker bases, compared to substitution of isomers in the meta and para position. Electrophilic aromatic substitution of disubstituted benzene compounds causes steric effects which determines the regioselectivity of an incoming electrophile in disubstituted benzene ...
[11] [page needed]) For ortho-para directing groups (electron donating group or EDG), σ’ more positive than σ meta and σ para. The difference between σ para and σ’ (σ para – σ’) is greater than that between σ meta and σ’(σ meta − σ’). This is expected as electron resonance effects are felt more strongly at the p-positions.