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  2. Phenyl group - Wikipedia

    en.wikipedia.org/wiki/Phenyl_group

    It is generally considered an inductively withdrawing group (-I), because of the higher electronegativity of sp 2 carbon atoms, and a resonance donating group (+M), due to the ability of its π system to donate electron density when conjugation is possible. [5] The phenyl group is hydrophobic. Phenyl groups tend to resist oxidation and reduction.

  3. Electrophilic aromatic directing groups - Wikipedia

    en.wikipedia.org/wiki/Electrophilic_aromatic...

    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.

  4. Dakin oxidation - Wikipedia

    en.wikipedia.org/wiki/Dakin_oxidation

    Adding boric acid to the acid-catalyzed reaction mixture increases the yield of phenol product over phenyl carboxylic acid product, even when using phenyl aldehyde or ketone reactants with electron-donating groups meta to the carbonyl group or electron-withdrawing groups ortho or para to the carbonyl group. Boric acid and hydrogen peroxide form ...

  5. Mesomeric effect - Wikipedia

    en.wikipedia.org/wiki/Mesomeric_effect

    The +M effect, also known as the positive mesomeric effect, occurs when the substituent is an electron donating group. The group must have one of two things: a lone pair of electrons, or a negative charge. In the +M effect, the pi electrons are transferred from the group towards the conjugate system, increasing the density of the system.

  6. Arene substitution pattern - Wikipedia

    en.wikipedia.org/wiki/Arene_substitution_pattern

    Trimethylsilyl, tert-butyl, and isopropyl groups can form stable carbocations, hence are ipso directing groups. Meso-substitution refers to the substituents occupying a benzylic position. It is observed in compounds such as calixarenes and acridines. Peri-substitution occurs in naphthalenes for substituents at the 1 and 8 positions. [citation ...

  7. Inductive effect - Wikipedia

    en.wikipedia.org/wiki/Inductive_effect

    In Organic chemistry, the inductive effect in a molecule is a local change in the electron density due to electron-withdrawing or electron-donating groups elsewhere in the molecule, resulting in a permanent dipole in a bond. [1] It is present in a σ (sigma) bond, unlike the electromeric effect which is present in a π (pi) bond.

  8. Pi electron donor-acceptor - Wikipedia

    en.wikipedia.org/wiki/Pi_electron_donor-acceptor

    The more positive is the value of pEDA the more pi-electron donating is a substituent. The more negative pEDA, the more pi-electron withdrawing is the substituent (see the table below). The pEDA parameter for a given substituent is calculated by means of quantum chemistry methods. The model molecule is the monosubstituted benzene.

  9. Captodative effect - Wikipedia

    en.wikipedia.org/wiki/Captodative_effect

    The captodative effect is the stabilization of radicals by a synergistic effect of an electron-withdrawing substituent and an electron-donating substituent. [2] [3] The name originates as the electron-withdrawing group (EWG) is sometimes called the "captor" group, whilst the electron-donating group (EDG) is the "dative" substituent. [3]