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An electron-withdrawing group (EWG) is a group or atom that has the ability to draw electron density toward itself and away from other adjacent atoms. [1] This electron density transfer is often achieved by resonance or inductive effects.
Delocalizing the radical ion stabilizes the transition state structure. As a result, the energy of activation decreases, enhancing the rate of the overall reaction. According to the captodative effect, the rate of a reaction is the greatest when both the EDG and EWG are able to delocalize the radical ion in the transition state structure. [7]
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.
In organic chemistry, the term stereoelectronic effect is also used to emphasize the relation between the electronic structure and the geometry (stereochemistry) of a molecule. The term polar effect is sometimes used to refer to electronic effects, but also may have the more narrow definition of effects resulting from non-conjugated substituents.
In 1998, Mander et al. synthesized the diterpenoid tropone, harringtonolide [6] using the Buchner intramolecular ring expansion annulation chemistry. A rhodium catalyst (Rh 2 (mandelate) 4) and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) were used to generate the carbene. This natural product was found to have antineoplastic and antiviral properties.
The overall reaction mechanism, denoted by the Hughes–Ingold mechanistic symbol S E Ar, [3] begins with the aromatic ring attacking the electrophile E + (2a). This step leads to the formation of a positively charged and delocalized cyclohexadienyl cation, also known as an arenium ion, Wheland intermediate, or arene σ-complex (2b).
An example of the E1cB reaction mechanism in the degradation of a hemiketal under basic conditions. The E1cB elimination reaction is a type of elimination reaction which occurs under basic conditions, where the hydrogen to be removed is relatively acidic, while the leaving group (such as -OH or -OR) is a relatively poor one.
Reductive elimination is an elementary step in organometallic chemistry in which the oxidation state of the metal center decreases while forming a new covalent bond between two ligands. It is the microscopic reverse of oxidative addition, and is often the product-forming step in many catalytic processes. Since oxidative addition and reductive ...